Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.
   
Martha's Vineyard Vacation Rentals

Oak Bluffs Vacation Rentals

Oak Bluffs is known for its whimsical "gingerbread" houses, many of which were built in the nineteenth century. A popular family vacation area, Oak Bluffs has several public parks, including Ocean Park with its live music throughout the summer.

251 properties
Oak Bluffs Guide
A fee-based feature highlighting availability within the next 4 weeks.

Oak Bluffs vacation rentals that sleep 20
Oak Bluffs
ID 5533
9 BR
4 baths
Sleeps 20
Villa Rosa- Historic Waterfront Victorian Mansion 1875 Gem
Villa Rosa- Historic Waterfront Victorian Mansion 1875 Gem
Distance to beach: Across the street (no obstruction) Oak Bluffs Town Beach and 5 min drive, 15 min bike State Beach
4.86 reviews
Summer:
 $20,000 - $40,000/wk
Off Season:
 $2,500 - $4,000/night
 $10,000 - $30,000/wk
 $30,000 - $50,000/mo

Oak Bluffs vacation rentals that sleep 18
Oak Bluffs
ID 39396
9 BR
3 ½ baths
Sleeps 18
OCEANFRONT SLEEPS 18 PRIME LOCATION!
OCEANFRONT SLEEPS 18 PRIME LOCATION!
Distance to beach: Steps to beach Oak Bluffs Town Beach and Inkwell Beach, State Beach, East ville Beach
OWNER SPECIAL:
Great Location reduce rate for June & July please call asap Book Now !
Summer:
 $15,500 - $30,000/wk
Off Season:
 $15,500 - $18,000/wk
Oak Bluffs
ID 38152
9 BR
6 ½ baths
Sleeps 18
Spectacular Views Completely Updated w/Guest Home- Sleeps 18
Spectacular Views Completely Updated w/Guest Home- Sleeps 18
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Summer:
 $26,000 - $32,000/wk
Off Season:
 $1,200 - $1,500/night
 $15,000 - $30,000/wk

Oak Bluffs vacation rentals that sleep 16
East Chop-Oak Bluffs
ID 14646
8 BR
3 baths
Sleeps 16
Historic East Chop Beach House - NEW PROMO ON OPEN JULY WKS
Historic East Chop Beach House - NEW PROMO ON OPEN JULY WKS
Distance to beach: 300 ft to Jetty Beach
5.07 reviews
Summer:
 $8,500 - $14,000/wk
Off Season:
 $10,500/wk
3
Historic Copeland District
ID 35193
8 BR
3 baths
Sleeps 16
8 BR Grand Victorian near Inkwell Beach sleeps 16 people!
8 BR Grand Victorian near Inkwell Beach sleeps 16 people!
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Summer:
 $13,700 - $19,500/wk
Off Season:
 $1,500 - $2,000/night
 $9,500 - $11,700/wk
Oak Bluffs
ID 28357
6 BR
4 ½ baths
Sleeps 16
Beautiful, Newly Updated, Spacious 6 BR Home
Beautiful, Newly Updated, Spacious 6 BR Home
Distance to beach: 3 miles to Oak Bluffs Inkwell Beach
4.815 reviews
Summer:
 $12,000 - $15,000/wk
Off Season:
 $10,000 - $12,000/wk
5

Oak Bluffs vacation rentals that sleep 15
Oak Bluffs
ID 11056
6 BR
2 ½ baths
Sleeps 15
Beach, Town, and Tennis, Central AC, 100% Renew. Energy.
Beach, Town, and Tennis, Central AC, 100% Renew. Energy.
Distance to beach: 3/10 mi to Inkwell Beach, Oak Bluffs
5.013 reviews
Summer:
 $6,950 - $9,800/wk
Off Season:
 $5,900 - $6,900/wk
4
Oak Bluffs
ID 39526
6 BR
4 baths
Sleeps 15
Island Escape with Water-Views; Lap Pool & Guest House
Island Escape with Water-Views; Lap Pool & Guest House
Distance to beach: 1 mi to The Jetty Beach and 1/2 mi to Eastville Beach
Summer:
 $17,500 - $21,000/wk
 $50,000 - $80,000/mo
Off Season:
 $1,500/night
 $10,500 - $13,000/wk
 $6,000 - $50,000/mo
5

Oak Bluffs vacation rentals that sleep 14
Oak Bluffs
ID 35126
7 BR
4 baths
Sleeps 14
Historic Victorian Home With Ocean Views & AC
Historic Victorian Home With Ocean Views & AC
Distance to beach: 0.3 mile Oak Bluffs Town Beach
OWNER SPECIAL:
10% Price drop in July weeks of 7/12-7/19 and 7/26-8/2.
Summer:
 $16,500 - $21,700/wk
Off Season:
 $9,000 - $16,500/wk
Oak Bluffs
ID 39105
5 BR
4 ½ baths
Sleeps 14
The Driftwood House Waterfront Retreat, Walk to the Inkwell
The Driftwood House Waterfront Retreat, Walk to the Inkwell
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
 $12,500 - $22,000/wk
Off Season:
 $7,000 - $14,000/wk
4

Oak Bluffs vacation rentals that sleep 13
Oak Bluffs
ID 35046
6 BR
2 baths
Sleeps 13
Air Conditioned Oak Bluffs Waterview Victorian. In Town
Air Conditioned Oak Bluffs Waterview Victorian. In Town
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
5.010 reviews
Summer:
 $7,500 - $12,000/wk
Off Season:
 $4,000 - $4,500/wk

Oak Bluffs vacation rentals that sleep 12
Oak Bluffs
ID 32999
7 BR
2 ½ baths
Sleeps 12
In Town Oak Bluffs w/AC Beautifully Renovated Victorian
In Town Oak Bluffs w/AC Beautifully Renovated Victorian
Distance to beach: 3/10 mile To Oak Bluffs Town Beach
5.011 reviews
Summer:
 $9,000 - $12,000/wk
Off Season:
 $9,000/wk
6
Oak Bluffs (East Chop)
ID 11709
6 BR
4 baths
Sleeps 12
Martha's Vineyard Memories, 1860 Sea Captain's Beach Home!
Martha's Vineyard Memories, 1860 Sea Captain's Beach Home!
Distance to beach: 5 minute bike ride to Sunny Jetty Beach!
5.012 reviews
OWNER SPECIAL:
CANCELLATION SPECIAL HUGE MULTI-WEEK DISCOUNT.
Summer:
 $7,999/wk
Off Season:
 $6,499 - $7,999/wk
2
Oak Bluffs
ID 22593
6 BR
3 baths
Sleeps 12
Charming 5+ BR Renovated Camp on Lagoon Pond w/ Guest Cabin
Charming 5+ BR Renovated Camp on Lagoon Pond w/ Guest Cabin
Distance to beach: Private beach on the Lagoon
5.09 reviews
Summer:
 $6,700 - $14,000/wk
Off Season:
 $600 - $900/night
 $4,900 - $5,900/wk
6
East Chop
ID 23099
6 BR
4 ½ baths
Sleeps 12
Family Compound on East Chop
Family Compound on East Chop
Distance to beach: two tenths mile to lovely Jetty Beach
5.02 reviews
Summer:
 $5,700 - $8,500/wk
Off Season:
 $3,000 - $6,500/wk
East Chop
ID 23424
6 BR
4 ½ baths
Sleeps 12
7/6-7/13 OPEN DUE TO CANCELLATION! Walk to Town and Beach!
7/6-7/13 OPEN DUE TO CANCELLATION! Walk to Town and Beach!
Distance to beach: 3/10 of a mile, 5 minute walk The Jetty Beach
5.03 reviews
Summer:
 $9,000 - $14,000/wk
Off Season:
 $600 - $1,500/night
 $2,000 - $9,000/wk
4
East Chop
ID 20680
6 BR
2 baths
Sleeps 12
East Chop Martha’s Vineyard Waterfront Ocean View Rental
East Chop Martha’s Vineyard Waterfront Ocean View Rental
Distance to beach: 2/10 mile to Jetty Beach
5.02 reviews
OWNER SPECIAL:
10 Days in Early August Still Available! Book all 10 days, we'll discount it $1,500!
Summer:
 $6,000 - $8,000/wk
 $17,500 - $22,500/mo
Off Season:
 $4,500 - $7,000/wk
 $15,000/mo
Oak Bluffs
ID 33717
6 BR
3 baths
Sleeps 12
''The Carousel House'' - Ocean Park - Featured in NY Times
''The Carousel House'' - Ocean Park - Featured in NY Times
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $12,900 - $20,900/wk
Off Season:
 $1,575/night
 $5,000 - $12,900/wk
2
The Radcliffe House
ID 37237
6 BR
2 baths
Sleeps 12
Beautiful newly renovated 6bd/ 3 block from beach
Beautiful newly renovated 6bd/ 3 block from beach
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
5.08 reviews
Summer:
 $7,500 - $10,500/wk
Off Season:
 $745 - $2,000/night
 $5,000 - $8,000/wk
Highlands Section of East Chop
ID 8766
6 BR
2 baths
Sleeps 12
Oak Bluffs Harbor view...walk to town & beach
Oak Bluffs Harbor view...walk to town & beach
Distance to beach: 6/10 mile to Oak Bluffs Town Beach and 3/10 mile to public Jetty Beach
5.031 reviews
Summer:
 $6,500/wk
Off Season:
 $850 - $1,050/night
Oak Bluffs
ID 37925
6 BR
4 baths
Sleeps 12
Oak Bluffs Luxury Compound with Carriage House & Pool/Spa
Oak Bluffs Luxury Compound with Carriage House & Pool/Spa
Distance to beach: 3.7 miles to Inkwell Beach Oak Bluffs Town Beach and 8.7 miles to South Beach (Katama) South Beach - Katama
Summer:
 $16,500 - $20,000/wk
 $100,000/mo
Off Season:
 $1,300/night
 $9,100 - $20,000/wk
5
Oak Bluffs
ID 38331
6 BR
3 ½ baths
Sleeps 12
6 Bedroom house for rent in Oak Bluffs, sleeps 12
6 Bedroom house for rent in Oak Bluffs, sleeps 12
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
July 5, & 12th are still available Book before there gone !
Summer:
 $8,500 - $11,500/wk
Off Season:
 $8,500 - $11,500/wk
Ocean Park
ID 40356
6 BR
2 ½ baths
Sleeps 12
Available Weeks of 7/26/25 & 8/24/25! Ocean Park Beauty!
Available Weeks of 7/26/25 & 8/24/25! Ocean Park Beauty!
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
available week of 7/26/25 and 8/23/25.
Summer:
 $8,500 - $16,500/wk
Off Season:
 $7,500 - $8,500/wk
Lagoon Pond Salt-Waterfront
ID 27817
5 BR
3 ½ baths
Sleeps 12
Glorious Sunsets On and Over the Water. Beautiful Home
Glorious Sunsets On and Over the Water. Beautiful Home
Distance to beach: Private beach, 6 kayak,4-SUPs, beach chairs & TOYS
5.030 reviews
LAST MINUTE ALERT 8/9 - 8/16
OWNER SPECIAL:
SUPER SPECIAL: 7/19-26 just reduced to $9.5 (w/rnd-trip auto res) MORE dscnt if 8 or <.
Summer:
 $9,500 - $20,000/wk
Off Season:
 $2,000 - $2,500/night
 $6,500 - $12,000/wk
 $25,000 - $30,000/mo
11
Oak Bluffs
ID 26970
5 BR
2 ½ baths
Sleeps 12
AMENITIES GALORE, DOCK/TENNIS/AC IN PRIVATE COMMUNITY
AMENITIES GALORE, DOCK/TENNIS/AC IN PRIVATE COMMUNITY
Distance to beach: 3 miles to Joseph Sylvia State Beach
5.03 reviews
Summer:
 $7,500 - $12,000/wk
Off Season:
 $5,000 - $7,500/wk
2
Oak Bluffs
ID 31220
5 BR
2 ½ baths
Sleeps 12
CENTRAL AC! Walk 2 Town and Beach. Game room w/arcade games
CENTRAL AC! Walk 2 Town and Beach. Game room w/arcade games
Distance to beach: 1/2 mile to Jetty beach
16 reviews
Summer:
 $6,000 - $7,300/wk
Off Season:
 $7,300/wk
3
Harthaven
ID 31261
5 BR
3 ½ baths
Sleeps 12
The Beach House: Historic Harthaven Gem on a Private Beach
The Beach House: Historic Harthaven Gem on a Private Beach
Distance to beach: On a private beach & next to an association beach
5.01 review
Summer:
 $9,000 - $9,500/wk
Off Season:
 $7,000 - $9,000/wk
Oak Bluffs
ID 32994
5 BR
3 baths
Sleeps 12
Walk to Town & Beach from this Beautiful Waban Park Cottage
Walk to Town & Beach from this Beautiful Waban Park Cottage
Distance to beach: 2 blocks to Oak Bluffs Town Beach
5.011 reviews
Summer:
 $6,000 - $10,000/wk
Off Season:
 $5,000 - $5,250/wk
East Chop
ID 37848
5 BR
5 ½ baths
Sleeps 12
Black Ivy Cottage - Direct Oceanfront in East Chop/Sleeps 12
Black Ivy Cottage - Direct Oceanfront in East Chop/Sleeps 12
Distance to beach: 1/10 mi to The Jetty Beach and 1/10 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $15,000 - $20,000/wk
Off Season:
 $1,500 - $1,660/night
 $12,500 - $15,000/wk
3
Oak Bluffs
ID 38997
5 BR
2 baths
Sleeps 12
** Newly Renovated home 2 Minutes away from Circuit Ave
** Newly Renovated home 2 Minutes away from Circuit Ave
Distance to beach: 1.4 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
 $6,500 - $9,200/wk
 $26,300 - $30,000/mo
Off Season:
 $3,500 - $7,000/wk
4
Oak Bluffs
ID 39247
5 BR
6 ½ baths
Sleeps 12
Luxurious Coastal-Style Living With Pool In The Preserve
Luxurious Coastal-Style Living With Pool In The Preserve
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
1 review
Summer:
 $18,000 - $30,000/wk
Off Season:
 $1,500 - $2,860/night
 $10,000 - $20,000/wk
Oak Bluffs
ID 11575
5 BR
3 ½ baths
Sleeps 12
Joy, historic 5 bedroom home in the heart Oak Bluffs
Joy, historic 5 bedroom home in the heart Oak Bluffs
Distance to beach: 1/2 mile
5.01 review
Summer:
 $3,500 - $4,200/wk
Off Season:
 $2,000 - $2,800/night
 $3,000 - $3,500/wk
3
Oak Bluffs
ID 37162
4 BR
2 ½ baths
Sleeps 12
Vineyard Seven/Sleeps 12/Tennis Courts/Centrally Located
Vineyard Seven/Sleeps 12/Tennis Courts/Centrally Located
Distance to beach: 2.7 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $6,000 - $14,000/wk
Off Season:
 $850 - $925/night
 $3,000 - $10,500/wk
Oak Bluffs
ID 38638
4 BR
3 ½ baths
Sleeps 12
Ideal Coastal Home Close to Circuit Ave
Ideal Coastal Home Close to Circuit Ave
Distance to beach: 1.5 mi to Oak Bluffs Town Beach
Summer:
 $10,000/wk
Off Season:
 $550 - $650/night
 $2,500 - $6,500/wk
4
Oak Bluffs
ID 38518
4 BR
3 baths
Sleeps 12
Pool, Hot Tub, Pool Bar...Perfect for Entertaining!
Pool, Hot Tub, Pool Bar...Perfect for Entertaining!
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
Summer:
 $10,000/wk
Off Season:
 $1,375 - $1,600/night
 $5,000/wk
2

Oak Bluffs vacation rentals that sleep 11
East Chop
ID 34693
5 BR
5 ½ baths
Sleeps 11
East Chop Beautiful Renovated Cottage, 5 Bedrooms + 5 Baths
East Chop Beautiful Renovated Cottage, 5 Bedrooms + 5 Baths
Distance to beach: 7/10 mi to The Jetty Beach
5.02 reviews
OWNER SPECIAL:
July 22-26 available (special price!) - last opening for the summer!
Summer:
 $4,500 - $10,500/wk
Off Season:
 $750 - $1,000/night
 $6,500/wk
 $16,000 - $20,000/mo
6
Oak Bluffs
ID 35433
5 BR
4 baths
Sleeps 11
Beautiful home, game room/pool table, Large Patio & Yard
Beautiful home, game room/pool table, Large Patio & Yard
Distance to beach: 2.9 mi to Oak Bluffs Town Beach and 4.0 mi to State Beach
5.03 reviews
OWNER SPECIAL:
Rentals include electric car charger for additional cost.
Summer:
 $6,900 - $9,100/wk
Off Season:
 $850 - $950/night
 $3,500 - $8,600/wk
3
Oak Bluffs
ID 33881
5 BR
1 ½ bath
Sleeps 11
Beach and downtown OB walkable! 5 Bedroom Victorian.
Beach and downtown OB walkable! 5 Bedroom Victorian.
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
4.73 reviews
Summer:
 $7,750/wk
Off Season:
 $420 - $650/night
 $3,000 - $4,500/wk
Oak Bluffs
ID 39520
4 BR
4 baths
Sleeps 11
Heated Pool/Spa/Poolhouse; Home Theatre, Outdoor Dining
Heated Pool/Spa/Poolhouse; Home Theatre, Outdoor Dining
Distance to beach: 2.2 mi to Oak Bluffs Town Beach
Summer:
 $18,500 - $22,500/wk
 $67,000 - $80,000/mo
Off Season:
 $2,000 - $3,000/night
 $15,000 - $22,500/wk
 $45,000 - $62,000/mo
5
East Chop
ID 34601
4 BR
3 baths
Sleeps 11
Dempster Park of East Chop: Walk to Beach & Town!
Dempster Park of East Chop: Walk to Beach & Town!
Distance to beach: Jetty Beach Oak Bluffs Town Beach
5.07 reviews
Summer:
 $6,000 - $8,000/wk
Off Season:
 $571/night
 $4,000 - $6,000/wk
5

Oak Bluffs vacation rentals that sleep 10
Oak Bluffs
ID 12900
6 BR
3 baths
Sleeps 10
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Distance to beach: 3/10 mi to Jetty Beach
5.03 reviews
LAST MINUTE ALERT 8/4 - 8/11
OWNER SPECIAL:
Last minute availability 8/4-11 with ferry tics.
Summer:
 $4,000 - $7,000/wk
Off Season:
 $2,000/night
 $4,000/wk
 $10,000/mo
2
Oak Bluffs
ID 29386
6 BR
2 baths
Sleeps 10
Charming House on Waban Park, Walk to Beach, Town, & Ferry!
Charming House on Waban Park, Walk to Beach, Town, & Ferry!
Distance to beach: 2 blocks from the Inkwell (Town Beach)
4.97 reviews
Summer:
 $4,500 - $10,000/wk
Off Season:
 $800/night
 $2,000 - $6,900/wk
3
Oak Bluffs
ID 18823
6 BR
2 baths
Sleeps 10
Charming, 6 Bedroom Victorian Gingerbread
Charming, 6 Bedroom Victorian Gingerbread
Distance to beach: One block State Beach and One block to Sea View Ave & Town Beach.
4.812 reviews
Summer:
 $7,500 - $8,500/wk
Off Season:
 $7,500/wk
4
Oak Bluffs
ID 3540
5 BR
3 baths
Sleeps 10
Magnificent Spacious Modern Home
Magnificent Spacious Modern Home
Distance to beach: O.7 miles Oak Bluffs Town Beach and 0.7 miles Eastville Beach
4.68 reviews
Summer:
 $5,500 - $6,500/wk
Off Season:
 $2,000 - $6,500/wk
 $3,500 - $5,000/mo
2
Oak Bluffs
ID 11040
5 BR
2 baths
Sleeps 10
Ocean Peek Cottage
Ocean Peek Cottage
Distance to beach: Two blocks
5.06 reviews
LAST MINUTE ALERT 7/27 - 8/3
OWNER SPECIAL:
Discounted week- $4300- available due to last minute cancellation- 5 min to shops and beach of OB!
Summer:
 $4,300 - $4,600/wk
Off Season:
 $1,600 - $4,600/wk
2
Oak Bluffs
ID 19414
5 BR
2 baths
Sleeps 10
No need for car -- walk from ferry! Beach & water views
No need for car -- walk from ferry! Beach & water views
Distance to beach: ~30 yards to Inkwell Beach
5.03 reviews
Summer:
 $7,000 - $12,200/wk
Off Season:
 $7,000 - $10,000/wk
3
Oak Bluffs
ID 26885
5 BR
1 ½ bath
Sleeps 10
Great Location, Water Views, AC & Steps from Inkwell Beach
Great Location, Water Views, AC & Steps from Inkwell Beach
Distance to beach: 75 yards to the Inkwell beach
5.05 reviews
Summer:
 $10,500/wk
Off Season:
 $8,500 - $10,500/wk
Oak Bluffs
ID 33204
5 BR
3 baths
Sleeps 10
AKWAABA Manor Marthas Vineyard
AKWAABA Manor Marthas Vineyard
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
Summer:
 $17,000 - $21,500/wk
 $40,000 - $55,000/mo
Off Season:
 $1,100 - $2,500/night
 $11,000 - $17,500/wk
 $25,000 - $40,000/mo
2
Oak Bluffs
ID 33370
5 BR
3 baths
Sleeps 10
CENTRAL AIR! Walk to town, Porch, 5 bedrooms & 3 bathrooms
CENTRAL AIR! Walk to town, Porch, 5 bedrooms & 3 bathrooms
Distance to beach: 15 minute walk to (5/10 of a mile) State Beach
5.013 reviews
Summer:
 $8,500 - $9,700/wk
Off Season:
 $5,000 - $9,000/wk
4
Historic Copeland District
ID 34083
5 BR
2 baths
Sleeps 10
''The Legacy House'' - A Historic Beauty near beach & town
''The Legacy House'' - A Historic Beauty near beach & town
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
4.54 reviews
LAST MINUTE ALERT 7/6 - 7/13
OWNER SPECIAL:
Prime July Weeks!! $400 Off listed price.
Summer:
 $5,500 - $8,800/wk
Off Season:
 $650 - $900/night
 $4,000 - $6,000/wk
6
Oak Bluffs - East Chop
ID 29421
5 BR
3 ½ baths
Sleeps 10
Vineyard Sound & Lake Views - Watch Ferries & Sunsets
Vineyard Sound & Lake Views - Watch Ferries & Sunsets
Distance to beach: 3/4 mile Oak Bluffs Town Beach, E Chop Beach Club
Summer:
 $7,500 - $8,500/wk
Off Season:
 $800 - $1,200/night
 $4,000 - $8,500/wk
 $8,000 - $16,000/mo
6
Oak Bluffs
ID 34390
5 BR
3 baths
Sleeps 10
This is one Summer School you won't want to miss!
This is one Summer School you won't want to miss!
Distance to beach: 7/10 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
 $7,000 - $11,000/wk
Off Season:
 $5,000 - $7,750/wk
4
Oak Bluffs
ID 34661
5 BR
5 ½ baths
Sleeps 10
5 BR SUITES, SALT WATER POOL, CENTRAL AIR, BIKE PATH
5 BR SUITES, SALT WATER POOL, CENTRAL AIR, BIKE PATH
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Great weeks are still available July 6 & 20th are still opened Book Now !
Summer:
 $15,000 - $30,000/wk
Off Season:
 $15,000/wk
Oak Bluffs
ID 35217
5 BR
3 baths
Sleeps 10
The “Summer Wind” House - Walk to the Beach!
The “Summer Wind” House - Walk to the Beach!
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
 $9,000 - $18,000/wk
Off Season:
 $6,000 - $10,000/wk
Oak Bluffs
ID 34333
5 BR
3 baths
Sleeps 10
The Mission House Waterviews of Nantucket Sound & Farm Pond
The Mission House Waterviews of Nantucket Sound & Farm Pond
Distance to beach: 2/10 mi to Oak Bluffs Town Beach and 1/10 mi to Inkwell Beach
5.01 review
Summer:
 $14,500 - $17,500/wk
3
Oak Bluffs
ID 38822
5 BR
4 baths
Sleeps 10
Stylish In-town Gingerbread in the Center of EVERYTHING!
Stylish In-town Gingerbread in the Center of EVERYTHING!
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
3 reviews
OWNER SPECIAL:
Price Reduction Summer Weeks Available, Walk to Beach - Won't Last.
Summer:
 $6,000 - $13,000/wk
Off Season:
 $900 - $1,200/night
 $5,000 - $8,500/wk
In Town and Near Beach
ID 40567
5 BR
2 ½ baths
Sleeps 10
Oak Bluffs in Town & Walk to Beach-Illumination Week Open
Oak Bluffs in Town & Walk to Beach-Illumination Week Open
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
Summer:
 $8,500 - $20,000/wk
Off Season:
 $8,000 - $8,500/wk
Oak Bluffs
ID 40573
5 BR
3 ½ baths
Sleeps 10
Charming Family Vineyard Getaway
Charming Family Vineyard Getaway
Distance to beach: 8/10 mile to Oak Bluffs Town Beach and Sailing camp, association private beach
Summer:
 $8,000 - $12,500/wk
Off Season:
 $5,500 - $8,300/wk
Oak Bluffs
ID 4132
5 BR
3 baths
Sleeps 10
Waterfront with its own Private Sandy Beach ! ! !
Waterfront with its own Private Sandy Beach ! ! !
Distance to beach: 0 feet to our beach; 1-1/2 miles to Vinyd beaches
5.06 reviews
Summer:
 $6,500 - $7,900/wk
Off Season:
 $4,000 - $7,900/wk
2
Oak Bluffs
ID 27415
5 BR
2 baths
Sleeps 10
Lovely Old Lady
Lovely Old Lady
Distance to beach: Inkwell beach under a 1/2 mile
5.025 reviews
Summer:
 $5,000 - $6,000/wk
Off Season:
 $4,000 - $4,500/wk
3
Oak Bluffs
ID 28697
5 BR
2 ½ baths
Sleeps 10
Discover your perfect getaway! Book now!
Discover your perfect getaway! Book now!
Distance to beach: 0.5 Oak Bluffs Town Beach and Town / Inkwell Beach yards away
5.01 review
OWNER SPECIAL:
Alert ! Rate reduced June 28,, August 9 & August 23, 2025—Book Now.
Summer:
 $8,500 - $16,500/wk
Off Season:
 $8,000 - $9,500/wk
Oak Bluffs
ID 34051
5 BR
2 baths
Sleeps 10
5 BR on Quiet East Chop Street, Steps to Beach
5 BR on Quiet East Chop Street, Steps to Beach
Distance to beach: 0.3 mi to The Jetty Beach
5.07 reviews
Summer:
 $4,350 - $6,850/wk
Off Season:
 $575/night
 $4,350/wk
2
Oak Bluffs
ID 34873
5 BR
2 baths
Sleeps 10
5 BR , Walk to Town and Inkwell Beach, Sleeps 10
5 BR , Walk to Town and Inkwell Beach, Sleeps 10
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Summer:
 $8,750 - $12,750/wk
Off Season:
 $8,750 - $10,750/wk
Waterview Farm
ID 38347
5 BR
2 ½ baths
Sleeps 10
Family Retreat in Private Setting
Family Retreat in Private Setting
Distance to beach: 1/2mi Oak Bluffs Town Beach and 2 miles - State Beach
Summer:
 $15,000 - $16,000/wk
Off Season:
 $1,250 - $1,500/night
 $15,000/wk
7
Oak Bluffs
ID 39273
5 BR
3 ½ baths
Sleeps 10
5 BR Victorian, AC, OCEAN PARK, FERRY,BEACHES,TOWN
5 BR Victorian, AC, OCEAN PARK, FERRY,BEACHES,TOWN
Distance to beach: Across the Street to Town/Inkwell Beaches
Summer:
 $7,500 - $14,000/wk
Off Season:
 $7,000 - $8,000/wk
Oak Bluffs
ID 31349
4 BR
2 baths
Sleeps 10
Steps to Beach! Newly Updated Cottage! Walk to Town/Ferry,AC
Steps to Beach! Newly Updated Cottage! Walk to Town/Ferry,AC
Distance to beach: 1/10 Mile to beach. ~150 feet Oak Bluffs Town Beach and The Inkwell Beach is steps away
4.86 reviews
OWNER SPECIAL:
Price Reduction!!! End of Summer Discount Available!!!
Summer:
 $8,000 - $13,000/wk
 $35,000 - $40,000/mo
Off Season:
 $500 - $1,000/night
 $5,000 - $6,000/wk
 $20,000 - $25,000/mo
3
Oak Bluffs
ID 33878
4 BR
3 baths
Sleeps 10
Amazing Gem w/AC, Guest House, Mooring & Private Sandy Beach
Amazing Gem w/AC, Guest House, Mooring & Private Sandy Beach
Distance to beach: 1 Oak Bluffs Town Beach and On Lagoon Pond; 137 feet of private, sandy beach
OWNER SPECIAL:
Special Opportunity Just Opened: August 16-22 price drop!
Summer:
 $13,000 - $21,000/wk
Off Season:
 $1,200 - $1,857/night
 $9,000 - $17,000/wk
5
Oak Bluffs
ID 33937
4 BR
2 baths
Sleeps 10
Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $5,500 - $9,500/wk
Off Season:
 $850/night
 $4,000 - $7,000/wk
Heart of Oak Bluffs
ID 34321
4 BR
5 ½ baths
Sleeps 10
Beautiful, Fully Renovated Gingerbread House on Ocean Park
Beautiful, Fully Renovated Gingerbread House on Ocean Park
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
5.08 reviews
Summer:
 $10,000 - $20,000/wk
Off Season:
 $6,000 - $10,000/wk
4
Oak Bluffs
ID 35269
4 BR
3 ½ baths
Sleeps 10
Contemporary 4 BR with central AC, tennis, kayaks, bikes
Contemporary 4 BR with central AC, tennis, kayaks, bikes
Distance to beach: 3.8 mi to Oak Bluffs Town Beach
Summer:
 $3,500 - $7,500/wk
Off Season:
 $600 - $800/night
 $3,500 - $4,500/wk
Oak Bluffs
ID 37186
4 BR
3 ½ baths
Sleeps 10
Ocean View Oak Bluffs 2023 full renovation
Ocean View Oak Bluffs 2023 full renovation
Distance to beach: 3.6 mi to Oak Bluffs Town Beach and 5 min walk to Sengekontacket Pond
5.04 reviews
LAST MINUTE ALERT 7/6 - 7/13
OWNER SPECIAL:
Week of July 6-13, 13-20 , 35% discount . Ferry tickets Sunday to Sunday available . No pets .
Summer:
 $5,000 - $12,000/wk
Off Season:
 $600 - $850/night
 $2,500 - $7,000/wk
5
Oak Bluffs
ID 37145
4 BR
2 baths
Sleeps 10
The Doll House - Your Dream Getaway on Martha’s Vineyard
The Doll House - Your Dream Getaway on Martha’s Vineyard
Distance to beach: 2.8 mi to Oak Bluffs Town Beach
5.07 reviews
Summer:
 $6,000 - $10,000/wk
Off Season:
 $650 - $800/night
 $6,000 - $8,000/wk
5
Oak Bluffs - Lagoon Pond
ID 37698
4 BR
2 ½ baths
Sleeps 10
Spacious 4-Bedroom Home in Oak Bluffs w/ Private Pool
Spacious 4-Bedroom Home in Oak Bluffs w/ Private Pool
Distance to beach: 3.3 mi to Oak Bluffs Town Beach and 3.6 mi to Owen Park Beach
5.04 reviews
OWNER SPECIAL:
Last-Minute Escape | Book Between July 13 - July 20 | 3-night Minimum Stay | Save 25% on Daily Rate.
Summer:
 $1,000 - $2,500/night
 $10,000 - $18,000/wk
Off Season:
 $700 - $1,400/night
 $5,000 - $10,000/wk
6
Oak Bluffs
ID 38330
4 BR
2 baths
Sleeps 10
The Tuck at Inkwell/Walk to Oak Bluffs Town Center & Beach
The Tuck at Inkwell/Walk to Oak Bluffs Town Center & Beach
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
Summer:
 $6,500 - $10,000/wk
Off Season:
 $4,000 - $6,500/wk
2
Oak Bluffs
ID 40393
4 BR
2 ½ baths
Sleeps 10
The Wishing Well - An Experience Worth Wishing For
The Wishing Well - An Experience Worth Wishing For
Distance to beach: 1.4 mi to Oak Bluffs Town Beach
Summer:
 $8,500 - $9,700/wk
 $36,000 - $38,800/mo
Off Season:
 $1,000 - $1,075/night
 $7,000 - $9,000/wk
 $28,000 - $32,000/mo
Oak Bluffs
ID 32791
4 BR
4 baths
Sleeps 10
AIR CONDITIONED Spacious Beach House w/Attached Studio Apt.
AIR CONDITIONED Spacious Beach House w/Attached Studio Apt.
Distance to beach: 1.8 mi To Oak Bluffs Town Beach
4.812 reviews
Summer:
 $3,850 - $7,700/wk
Off Season:
 $400 - $550/night
 $2,800 - $5,900/wk
3
Heritage Haven
ID 40508
3 BR
3 baths
Sleeps 10
Heritage Haven: AC, Steps to Town, Beach and Parks
Heritage Haven: AC, Steps to Town, Beach and Parks
Distance to beach: 0.4 mi to Oak Bluffs Town Beach
Summer:
 $1,200 - $1,500/night
 $7,000 - $12,000/wk
Off Season:
 $650 - $1,000/night
 $6,000 - $9,000/wk
6
Oak Bluffs
ID 39489
3 BR
2 ½ baths
Sleeps 10
The Purple Door in Heart of OB/Close to Beaches & Town
The Purple Door in Heart of OB/Close to Beaches & Town
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
Off Season:
 $1,350/wk
 $1,350 - $2,200/mo
6

Oak Bluffs vacation rentals that sleep 9
OBT2012
ID 34157
6 BR
2 baths
Sleeps 9
Charming OB 1885 Victorian Cottage
Charming OB 1885 Victorian Cottage
Distance to beach: 0.4 mi to The Jetty Beach
Summer:
 $4,700 - $6,000/wk
Off Season:
 $4,000 - $5,000/wk
Vineyard Haven
ID 38413
5 BR
3 ½ baths
Sleeps 9
Charming Vineyard Haven Home near Lagoon Pond
Charming Vineyard Haven Home near Lagoon Pond
Distance to beach: Short Distance to Lagoon Pond
Summer:
 $5,000 - $9,000/wk
Oak Bluffs, Copeland Historic
ID 22456
4 BR
3 baths
Sleeps 9
Solera - Ocean Views, Steps to Inkwell Beach
Solera - Ocean Views, Steps to Inkwell Beach
Distance to beach: Inkwell Beach is 1 short block away
5.021 reviews
Summer:
 $8,000 - $16,500/wk
Off Season:
 $850 - $1,100/night
 $7,000 - $8,000/wk
7
Oak Bluffs
ID 31591
4 BR
2 ½ baths
Sleeps 9
Oceanfront, steps to beach - walk to town & ferry!
Oceanfront, steps to beach - walk to town & ferry!
Distance to beach: 1/10 Oak Bluffs Town Beach and Oak Bluffs Town Beach (ocean) across the street
5.010 reviews
Summer:
 $10,800 - $16,900/wk
 $20,000 - $60,000/mo
Off Season:
 $7,900 - $12,500/wk
 $10,000 - $35,000/mo
5
Oak Bluffs
ID 33354
4 BR
3 baths
Sleeps 9
Enchanting Cottage with Central AC & Lagoon pond views
Enchanting Cottage with Central AC & Lagoon pond views
Distance to beach: 1.4 mi to Eastville Beach
OWNER SPECIAL:
OPEN JUNE 22ND & 29th GREAT WEEKS OPEN JULY 6th & 12th still available.
Summer:
 $8,500 - $11,500/wk
Off Season:
 $7,500 - $9,000/wk
Oak Bluffs
ID 38080
4 BR
4 ½ baths
Sleeps 9
East Chop, Newly Renovated 4BR, Walk to Beach & Downtown
East Chop, Newly Renovated 4BR, Walk to Beach & Downtown
Distance to beach: 1.1 mi to The Jetty Beach and 1/2 mi to Marinelli Beach East Chop
5.09 reviews
Summer:
 $6,000 - $11,000/wk
Off Season:
 $800 - $1,000/night
 $6,000 - $8,000/wk
3
Oak Bluffs
ID 39480
4 BR
2 ½ baths
Sleeps 9
Centrally Located Oak Bluffs Property next to Bike Path
Centrally Located Oak Bluffs Property next to Bike Path
Distance to beach: 4.8 mi to State Beach
5.01 review
Summer:
 $600 - $860/night
 $4,200 - $6,020/wk
Off Season:
 $790 - $860/night
 $4,200 - $6,020/wk
3
Oak Bluffs
ID 29856
4 BR
3 baths
Sleeps 9
Newly Renovated! Walk to Town Oak Bluffs 4 BR/3Bath A/C
Newly Renovated! Walk to Town Oak Bluffs 4 BR/3Bath A/C
Distance to beach: 1/2 m. to State Beach and 1/2 m. to East Chop Beach
Summer:
 $7,000 - $10,000/wk
Off Season:
 $650 - $1,000/night
 $4,550 - $8,000/wk
Oak Bluffs
ID 35803
4 BR
2 ½ baths
Sleeps 9
Tranquility in Oak Bluffs
Tranquility in Oak Bluffs
Distance to beach: 4.2 mi to Oak Bluffs Town Beach and 5.3 mi to State Beach
5.03 reviews
Summer:
 $6,000 - $6,500/wk
 $18,500/mo
Off Season:
 $3,000 - $6,000/wk
 $11,000 - $165,000/mo
Oak Bluffs
ID 38650
4 BR
3 baths
Sleeps 9
Cozy Cottage Near Inkwell Beach (New Build)
Cozy Cottage Near Inkwell Beach (New Build)
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
 $6,000 - $9,000/wk
Off Season:
 $430 - $1,200/night
 $4,000 - $6,000/wk
3
Oak Bluffs
ID 35107
3 BR
3 ½ baths
Sleeps 9
HEATED POOL/2 WHIRLPOOLS, CENTRAL AC,VIEW OF VINEYARD SOUND
HEATED POOL/2 WHIRLPOOLS, CENTRAL AC,VIEW OF VINEYARD SOUND
Distance to beach: 1 mi to Jetty (Marinelli) Beach, 0.3 mi to Eastvi
OWNER SPECIAL:
Two big weeks still available August 9th & Fireworks week August 16th Book Now.
Summer:
 $17,000/wk
Off Season:
 $10,000 - $17,000/wk

Oak Bluffs vacation rentals that sleep 8
Lagoon Pond Estates, Oak Bluff
ID 34037
5 BR
3 ½ baths
Sleeps 8
Salty Sanctuary with Deeded Access to Lagoon Pond
Salty Sanctuary with Deeded Access to Lagoon Pond
Distance to beach: 3.1 mi to Oak Bluffs Town Beach and 4.5 miles Eastville Beach
5.02 reviews
Summer:
 $4,200 - $6,500/wk
Off Season:
 $300 - $650/night
 $2,000 - $5,000/wk
6
Oak Bluffs
ID 21269
5 BR
1 ½ bath
Sleeps 8
5 BR, Oceanviews, Inkwell,Walk to Town, Ferry, Harbor
5 BR, Oceanviews, Inkwell,Walk to Town, Ferry, Harbor
Distance to beach: 100 Feet Oak Bluffs Town Beach and 100 feet to Inkwell Beach
OWNER SPECIAL:
GREAT LOCATION JULY WKS 13TH, 20TH AUG WKS 10TH & 24TH ARE OPEN !
Summer:
 $7,000/wk
Off Season:
 $7,000/wk
Oak Bluffs
ID 12116
4 BR
2 baths
Sleeps 8
Cape Style Home - has A/C ! short walk to Lagoon Beach
Cape Style Home - has A/C ! short walk to Lagoon Beach
Distance to beach: 4 minute walk to Lagoon Beach
5.06 reviews
Summer:
 $4,350/wk
Off Season:
 $2,600 - $4,350/wk
Oak Bluffs
ID 12643
4 BR
2 baths
Sleeps 8
Charming, Steps to Town & Beach, Central AC,
Charming, Steps to Town & Beach, Central AC,
Distance to beach: 4/10th's of a mile Oak Bluffs Town Beach and 10 minute walk
5.014 reviews
Summer:
 $4,900 - $6,900/wk
Off Season:
 $399 - $690/night
 $2,900 - $4,900/wk
5
Oak Bluffs
ID 9007
4 BR
3 ½ baths
Sleeps 8
Spacious Contemporary Cape in Private Cul de Sac
Spacious Contemporary Cape in Private Cul de Sac
Distance to beach: Ink Well 5 miles, State Beach 6, VH beaches 4
4.76 reviews
Summer:
 $4,300 - $6,300/wk
Off Season:
 $3,000 - $6,300/wk
East Chop
ID 28974
4 BR
2 baths
Sleeps 8
Adorable Oak Bluffs Cottage with AC on East Chop
Adorable Oak Bluffs Cottage with AC on East Chop
Distance to beach: 1/2 mile to Eastville Beach
5.06 reviews
Summer:
 $3,500 - $4,900/wk
Off Season:
 $500/night
 $3,150 - $4,200/wk
4
Oak Bluffs
ID 29717
4 BR
2 baths
Sleeps 8
Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
Distance to beach: Inkwell Beach approx. 1/2 a mile
4.86 reviews
Summer:
 $4,300 - $5,000/wk
Off Season:
 $600/night
 $4,300/wk
Oak Bluffs - Meadow View Farms
ID 29775
4 BR
4 ½ baths
Sleeps 8
Now offering flexible turnover for remaining 2025 weeks!
Now offering flexible turnover for remaining 2025 weeks!
Distance to beach: State Beach - 2 miles
4.934 reviews
Summer:
 $4,500 - $6,900/wk
Off Season:
 $600/night
 $3,500 - $5,800/wk
5
Walk to town, and beach, shops
ID 29080
4 BR
2 baths
Sleeps 8
Walk to town & beach(Oak Bluffs)4 bedrooms Air-conditioning
Walk to town & beach(Oak Bluffs)4 bedrooms Air-conditioning
Distance to beach: Oak Bluffs State Beach and 1/2 mile to Oak Bluffs town beach, East Chop beach
5.04 reviews
Summer:
 $1,000/night
 $5,000 - $10,000/wk
Off Season:
 $800 - $1,000/night
 $3,500 - $7,000/wk
9
Oak Bluffs
ID 28871
4 BR
2 baths
Sleeps 8
Cozy, Walk to town & Beach A/C, Kid & Dog friendly Welcome!
Cozy, Walk to town & Beach A/C, Kid & Dog friendly Welcome!
Distance to beach: Under 1/2 mile to Inkwell, Jetty and Pay Beach
5.05 reviews
LAST MINUTE ALERT 7/26 - 8/2
OWNER SPECIAL:
$500.00 Discount & Comes offering a Transferable ferry ticket! July 26-Aug 2nd. Inquire today.
Summer:
 $4,500 - $6,500/wk
Off Season:
 $3,500 - $5,500/wk
6
Oak Bluffs
ID 30339
4 BR
2 baths
Sleeps 8
Classic 4 B Cape in Eastville-Central AC & Heat!
Classic 4 B Cape in Eastville-Central AC & Heat!
Distance to beach: 1.5 miles Oak Bluffs Town Beach
5.08 reviews
Summer:
 $4,100 - $5,200/wk
Off Season:
 $3,300 - $5,000/wk
4
Oak Bluffs
ID 19178
4 BR
2 baths
Sleeps 8
Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
Distance to beach: 2 Blocks Oak Bluffs Town Beach and 2 Blocks The Jetty Beach
5.05 reviews
Summer:
 $3,000 - $13,000/wk
Off Season:
 $3,000/wk
 $2,800 - $4,000/mo
5
Oak Bluffs
ID 32817
4 BR
3 ½ baths
Sleeps 8
8/9-16 NOW OPEN! central A/C, heated saltwater pool,
8/9-16 NOW OPEN! central A/C, heated saltwater pool,
Distance to beach: 1 and 2/10 mile Oak Bluffs Town Beach and 3 miles State Beach
5.08 reviews
Summer:
 $10,000 - $16,500/wk
Off Season:
 $5,000 - $7,000/wk
Oak Bluffs
ID 33286
4 BR
2 baths
Sleeps 8
Lagoon Chic 4 Bedroom Family Home
Lagoon Chic 4 Bedroom Family Home
Distance to beach: 500 steps Eastville Beach and Inkwell Beach 1.2 miles
4.914 reviews
LAST MINUTE ALERT 7/13 - 7/20
OWNER SPECIAL:
Reduced rate! Week of July 13 and July 20 - Flex Arrival $500 night.
Summer:
 $450 - $500/night
 $2,500 - $4,620/wk
Off Season:
 $2,800 - $4,620/wk
3
Oak Bluffs
ID 31301
4 BR
2 ½ baths
Sleeps 8
Ocean Park Victorian Gem w/Sweeping Water Views
Ocean Park Victorian Gem w/Sweeping Water Views
Distance to beach: 30 yards from Oak Bluffs Town Beach and 150 yards to downtown.
5.01 review
Summer:
 $6,825 - $9,975/wk
Off Season:
 $4,000 - $7,000/wk
Meadow View Farms
ID 33786
4 BR
2 ½ baths
Sleeps 8
Peaceful Meadows
Peaceful Meadows
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
4.912 reviews
Summer:
 $4,200 - $5,200/wk
Off Season:
 $600/night
 $3,000 - $4,000/wk
4
Oak Bluffs
ID 34079
4 BR
4 baths
Sleeps 8
Beautiful 4 BR/4 BA Modern Victorian: The Mack on Winemack
Beautiful 4 BR/4 BA Modern Victorian: The Mack on Winemack
Distance to beach: 1.1 mi to The Jetty Beach and 1.3 to Inkwell Beach
4.914 reviews
Summer:
 $3,500 - $9,500/wk
Off Season:
 $2,500 - $4,500/wk
6
Oak Bluffs
ID 32194
4 BR
3 baths
Sleeps 8
Historical J. A. Norton House
Historical J. A. Norton House
Distance to beach: 1/10 mile Oak Bluffs Town Beach and 1 mile State Beach (Joseph Sylvia State Beach)
Summer:
 $5,000 - $10,000/wk
Off Season:
 $4,300 - $8,500/wk
Oak Bluffs
ID 35109
4 BR
3 ½ baths
Sleeps 8
Luxury Getaway At The Preserve
Luxury Getaway At The Preserve
Distance to beach: 2.5 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
10% Price drop in August weeks of 8/16-8/23 and 8/23-8/30.
Summer:
 $18,000 - $24,500/wk
Off Season:
 $19,000/wk
3
Oak Bluffs
ID 35166
4 BR
2 ½ baths
Sleeps 8
Fully Renovated Victorian 4 Br /2.5 Baths Steps To Inkwell
Fully Renovated Victorian 4 Br /2.5 Baths Steps To Inkwell
Distance to beach: 0.1 mi to Oak Bluffs Town Beach
5.07 reviews
Summer:
 $7,000 - $10,000/wk
Off Season:
 $500 - $1,000/night
 $4,000 - $7,500/wk
5
Oak Bluffs
ID 34211
4 BR
2 ½ baths
Sleeps 8
Charming Martha's Vineyard family cottage
Charming Martha's Vineyard family cottage
Distance to beach: 0.5 mi to The Jetty Beach and 1-2 mi to Oak Bluffs Town Beach
5.05 reviews
OWNER SPECIAL:
Best week of the entire summer Aug 23-31 is available at a lower rate of 3,500.
Summer:
 $3,500 - $4,000/wk
4
Oak Bluffs
ID 35483
4 BR
1 ½ bath
Sleeps 8
La Bella Sorella (The Beautiful Sister)
La Bella Sorella (The Beautiful Sister)
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
 $5,800 - $6,800/wk
Off Season:
 $5,800/wk
3
Oak Bluffs
ID 36320
4 BR
3 baths
Sleeps 8
Bright and Airy Oasis in OB
Bright and Airy Oasis in OB
Distance to beach: 1 mile Oak Bluffs Town Beach
6 reviews
LAST MINUTE ALERT 7/6 - 7/13
OWNER SPECIAL:
Massive discount - Current rental price(s) reflect 35% discount and includes all fees and taxes.
Summer:
 $6,000 - $8,400/wk
Off Season:
 $700/night
 $4,200/wk
2
Oak Bluffs
ID 36488
4 BR
2 ½ baths
Sleeps 8
Gingerbread Cottage with Amazing Oak Bluffs Harbor View
Gingerbread Cottage with Amazing Oak Bluffs Harbor View
Distance to beach: 4/10 mi to Oak Bluffs Town Beach and 5/10 mi to The Jetty Beach
Summer:
 $7,250 - $8,000/wk
Off Season:
 $7,250 - $7,500/wk
Oak Bluffs
ID 35858
4 BR
2 ½ baths
Sleeps 8
BRENDA'S COTTAGE! Walk to town, screened porch, 4bds/2.5ba
BRENDA'S COTTAGE! Walk to town, screened porch, 4bds/2.5ba
Distance to beach: 15 minute walk to The Jetty Beach!
5.07 reviews
Summer:
 $5,000 - $6,500/wk
Off Season:
 $3,500 - $5,000/wk
 $7,000 - $8,500/mo
5
Oak Bluffs
ID 34260
4 BR
2 ½ baths
Sleeps 8
Great central location, Central AC
Great central location, Central AC
Distance to beach: 4.0 mi to Oak Bluffs Town Beach
Summer:
 $8,500 - $8,900/wk
Off Season:
 $8,000/wk
Sengekontacket Association, Oa
ID 37096
4 BR
2 baths
Sleeps 8
Sun Filled Waterfront Home with a Beautiful Pond View
Sun Filled Waterfront Home with a Beautiful Pond View
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Car Ferry reservations are available for purchase for Sat to Sat in consultation with owner.
Summer:
 $5,500 - $8,000/wk
Off Season:
 $400 - $700/night
 $3,000 - $7,500/wk
Oak Bluffs
ID 37469
4 BR
2 baths
Sleeps 8
Classic Victorian Beauty Steps to Beach
Classic Victorian Beauty Steps to Beach
Distance to beach: 0.1 mi to Oak Bluffs Town Beach and Inkwell Beach
Summer:
 $6,200 - $9,000/wk
Off Season:
 $750 - $1,000/night
 $5,000/wk
Oak Bluffs
ID 32692
4 BR
4 ½ baths
Sleeps 8
Tranquility in Meadow View Farms - 4 BR with Central Air
Tranquility in Meadow View Farms - 4 BR with Central Air
Distance to beach: 2 miles to Oak Bluffs Town Beach
Summer:
 $11,000 - $12,000/wk
Off Season:
 $10,000/wk
2
Oak Bluffs
ID 38181
4 BR
2 baths
Sleeps 8
Quintessential East Chop Cottage - with A/C
Quintessential East Chop Cottage - with A/C
Distance to beach: 0.6 mi to The Jetty Beach
5.02 reviews
OWNER SPECIAL:
$500 off listed price for the weeks of July 12th and August 23rd.
Summer:
 $5,000 - $6,500/wk
Off Season:
 $700/night
 $3,500 - $5,000/wk
Oak Bluffs
ID 38312
4 BR
2 ½ baths
Sleeps 8
Spacious Oak Bluffs Farmhouse w/ Ferry Tickets
Spacious Oak Bluffs Farmhouse w/ Ferry Tickets
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $5,000 - $7,000/wk
Off Season:
 $3,500 - $5,000/wk
3
Oak Bluffs
ID 38862
4 BR
2 baths
Sleeps 8
Relaxing Oak Bluffs Getaway with A/C, Close to Town
Relaxing Oak Bluffs Getaway with A/C, Close to Town
Distance to beach: 0.9 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
 $4,200 - $5,700/wk
Off Season:
 $3,600 - $5,000/wk
1
East Chop Highlands
ID 39326
4 BR
2 baths
Sleeps 8
Cozy Cottage at Coleman Corners/Walk to Beach
Cozy Cottage at Coleman Corners/Walk to Beach
Distance to beach: 1/2 mi to The Jetty Beach
5.011 reviews
Summer:
 $3,500 - $4,500/wk
Off Season:
 $3,500 - $4,000/wk
3
Oak Bluffs
ID 39277
4 BR
2 baths
Sleeps 8
Spacious Colonial Summer Home
Spacious Colonial Summer Home
Distance to beach: .7 mi to The Jetty Beach
Summer:
 $2,950 - $5,300/wk
Off Season:
 $350 - $450/night
 $2,750 - $4,500/wk
Oak Bluffs
ID 38989
4 BR
3 ½ baths
Sleeps 8
Fabulous New 4 Bedroom in Oak Bluffs
Fabulous New 4 Bedroom in Oak Bluffs
Distance to beach: 1.6 mi to The Jetty Beach
OWNER SPECIAL:
July 27th now available! Ferry Ticket Available!
Summer:
 $4,200 - $7,200/wk
Off Season:
 $3,900 - $5,900/wk
2
The Historic Copeland District
ID 39629
4 BR
3 ½ baths
Sleeps 8
4 BR WALK TO INKWELL, TOWN, FERRY; AC
4 BR WALK TO INKWELL, TOWN, FERRY; AC
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Weeks are still available, just give us a call for June & July.
Summer:
 $11,175 - $20,000/wk
Off Season:
 $7,500 - $11,175/wk
Oak Bluffs
ID 39688
4 BR
2 baths
Sleeps 8
Vineyard Hills Beauty
Vineyard Hills Beauty
Distance to beach: 2.8 mi to Oak Bluffs Town Beach
Summer:
 $5,800 - $7,000/wk
Off Season:
 $600 - $1,000/night
 $3,500 - $5,000/wk
Oak Bluffs
ID 39711
4 BR
1 ½ bath
Sleeps 8
Beachfront Oasis within Minutes from Downtown
Beachfront Oasis within Minutes from Downtown
Distance to beach: 2/10 mi (108 feet) Oak Bluffs Town Beach
Summer:
 $6,000 - $12,000/wk
 $38,000 - $60,000/mo
Off Season:
 $650 - $1,000/night
 $3,000 - $6,500/wk
 $10,000 - $33,000/mo
Oak Bluffs
ID 39874
4 BR
4 ½ baths
Sleeps 8
Fabulous New Oak Bluffs 4 Bedroom Home with Pool ~ Sleeps 8
Fabulous New Oak Bluffs 4 Bedroom Home with Pool ~ Sleeps 8
Distance to beach: 2.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Price Reduction - Sun 8/24 - Sun 8/31.
Summer:
 $15,000 - $23,000/wk
Off Season:
 $1,428/night
Oak Bluffs
ID 39877
4 BR
4 ½ baths
Sleeps 8
Chic Contemporary Close to Downtown
Chic Contemporary Close to Downtown
Distance to beach: 3.1 mi to Oak Bluffs Town Beach
Summer:
 $6,200 - $8,000/wk
Off Season:
 $6,000 - $8,000/wk
Copeland/In Town
ID 39917
4 BR
1 ½ bath
Sleeps 8
In Town Victorian - Walk to Beach & Town
In Town Victorian - Walk to Beach & Town
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
Summer:
 $5,000 - $9,500/wk
Off Season:
 $500 - $1,250/night
 $2,000 - $6,000/wk
2
Oak Bluffs
ID 39932
4 BR
2 baths
Sleeps 8
Charming Oak Bluffs Home; Close to Circuit Ave & Beaches
Charming Oak Bluffs Home; Close to Circuit Ave & Beaches
Distance to beach: 0.7 mi to Oak Bluffs Town Beach and 0.5 mi to The Jetty Beach
Summer:
 $7,500/wk
3
Sengekontacket
ID 40084
4 BR
3 ½ baths
Sleeps 8
Serenity and Relaxation Await - Water Views and Pickleball
Serenity and Relaxation Await - Water Views and Pickleball
Distance to beach: 6 Miles Oak Bluffs Town Beach
OWNER SPECIAL:
Flexible Turnover Day!
Summer:
 $8,000 - $10,500/wk
Off Season:
 $5,000 - $7,500/wk
Oak Bluffs
ID 25368
4 BR
3 baths
Sleeps 8
Spacious retreat, just steps to Lagoon Beach - Great Value!!
Spacious retreat, just steps to Lagoon Beach - Great Value!!
Distance to beach: Lagoon Beach, approx. 500 feet
5.02 reviews
Summer:
 $535 - $640/night
 $3,750 - $4,500/wk
Off Season:
 $500 - $550/night
 $3,400 - $4,000/wk
5
Oak Bluffs
ID 26262
4 BR
1 ½ bath
Sleeps 8
La Sirena, The Mermaid Of Oak Bluffs
La Sirena, The Mermaid Of Oak Bluffs
Distance to beach: less than a mile Oak Bluffs Town Beach
4.98 reviews
Summer:
 $4,800 - $5,800/wk
Off Season:
 $4,800/wk
4
Oak Bluffs
ID 30502
4 BR
2 ½ baths
Sleeps 8
Spacious, Relaxing & Central Location!
Spacious, Relaxing & Central Location!
Distance to beach: 7-10 Minute Drive to OB & Edgartown Beaches
5.04 reviews
Summer:
 $6,100 - $7,500/wk
Off Season:
 $700 - $850/night
 $6,000 - $7,500/wk
Oak Bluffs
ID 31304
4 BR
2 baths
Sleeps 8
Classic waterfront Vict. cottage, walk to town; huge porch
Classic waterfront Vict. cottage, walk to town; huge porch
Distance to beach: Two blocks to Inkwell & OB town beach, Harthaven
5.018 reviews
Summer:
 $800 - $1,400/night
 $6,300 - $9,800/wk
Off Season:
 $600 - $1,200/night
 $2,000 - $7,700/wk
 $5,500 - $6,500/mo
3
Oak Bluffs
ID 32448
4 BR
2 ½ baths
Sleeps 8
Walk to Town/Walk to Beach in quiet location in OB (with AC)
Walk to Town/Walk to Beach in quiet location in OB (with AC)
Distance to beach: 3 blocks to Oak Bluffs Town Beach
5.04 reviews
Summer:
 $6,000 - $10,000/wk
Off Season:
 $5,000 - $7,000/wk
4
Oak Bluffs
ID 32868
4 BR
2 ½ baths
Sleeps 8
4 BR Home Inkwell Beach, Town, Basketball,Pickleball, Tennis
4 BR Home Inkwell Beach, Town, Basketball,Pickleball, Tennis
Distance to beach: 1 Oak Bluffs Town Beach and 5 minute walk to Oak BluffsTown & Inkwell Beaches
OWNER SPECIAL:
JUNE open July 5th & 12th Still Available.
Summer:
 $8,500 - $10,000/wk
Off Season:
 $7,500 - $8,500/wk
Oak Bluffs
ID 26201
4 BR
2 baths
Sleeps 8
Charming Cape near Lagoon and Town
Charming Cape near Lagoon and Town
Distance to beach: 3 Miles State Beach and 1 Mile Eastville Beach
Summer:
 $3,000/wk
Off Season:
 $400 - $600/night
 $3,000/wk
East Chop
ID 33664
4 BR
3 baths
Sleeps 8
CENTRAL AC,4 BR,EASTCHOP, EASTVILLE BEACH AUGUST OPEN!
CENTRAL AC,4 BR,EASTCHOP, EASTVILLE BEACH AUGUST OPEN!
Distance to beach: 8/10 mi to The Jetty Beach
OWNER SPECIAL:
GREAT WEEKS JUNE 28th JUly ,12TH & 19th.
Summer:
 $7,500 - $10,500/wk
Off Season:
 $7,500 - $8,750/wk
Oak Bluffs
ID 35279
4 BR
2 ½ baths
Sleeps 8
Your Own Peaceful Getaway w/AC in Oak Bluffs (Sorry No Pets)
Your Own Peaceful Getaway w/AC in Oak Bluffs (Sorry No Pets)
Distance to beach: 1.5 mi to Oak Bluffs Town Beach
5.06 reviews
Summer:
 $6,500 - $8,000/wk
Off Season:
 $4,500 - $6,500/wk
4
Oak Bluffs
ID 35412
4 BR
2 ½ baths
Sleeps 8
Charming 19Th Century Victorian Cottage In Oak Bluffs
Charming 19Th Century Victorian Cottage In Oak Bluffs
Distance to beach: 0.5 mi to The Jetty Beach and 0.8 mi to Oak Bluffs Town Beach
Summer:
 $5,500 - $6,000/wk
Off Season:
 $5,500 - $6,000/wk
Oak Bluffs - Near Farm Neck
ID 37842
4 BR
2 baths
Sleeps 8
Tree House Oak Bluffs
Tree House Oak Bluffs
Distance to beach: 1.7 mi to Oak Bluffs Town Beach
Summer:
 $6,250 - $7,500/wk
Off Season:
 $600 - $750/night
 $4,000 - $6,250/wk
2
Oak Bluffs
ID 38145
4 BR
3 baths
Sleeps 8
Hideaway At Meadow View Farm/Private Tennis Courts
Hideaway At Meadow View Farm/Private Tennis Courts
Distance to beach: 2.9 mi to Oak Bluffs Town Beach
5.05 reviews
Summer:
 $5,600 - $8,500/wk
Off Season:
 $430/night
 $3,500 - $7,700/wk
5
Oak Bluffs
ID 38972
4 BR
3 baths
Sleeps 8
Spacious Modern Vacation Rental, Great Getaway! BOOK NOW!
Spacious Modern Vacation Rental, Great Getaway! BOOK NOW!
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
GREAT HOME WKS OPEN JUNE JULY 13TH,20TH, 27TH & AUG 24TH. BOOK NOW/.
Summer:
 $7,000 - $12,500/wk
Off Season:
 $7,000/wk
Oak Bluffs
ID 38295
4 BR
2 baths
Sleeps 8
Island Paradise! Walk to Beach, Huge Deck, Pizza Oven
Island Paradise! Walk to Beach, Huge Deck, Pizza Oven
Distance to beach: 1/2 mile Eastville Beach
Summer:
 $7,500/wk
Off Season:
 $800 - $950/night
 $5,600 - $7,500/wk
Oak Bluffs
ID 35115
3 BR
3 ½ baths
Sleeps 8
Experience A Luxury Getaway By The Lagoon
Experience A Luxury Getaway By The Lagoon
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
Summer:
 $6,860 - $13,500/wk
Off Season:
 $4,000 - $8,000/wk
2
Oak Bluffs
ID 30781
3 BR
2 ½ baths
Sleeps 8
Hidden Treasure: Contemporary 3 BR Home w/Access to Tennis
Hidden Treasure: Contemporary 3 BR Home w/Access to Tennis
Distance to beach: 4.0 miles to most beaches .02 to sengekontacket
5.03 reviews
Summer:
 $4,000 - $5,000/wk
 $20,000/mo
Off Season:
 $2,000 - $4,500/wk
Historic Copeland District
ID 35575
3 BR
2 ½ baths
Sleeps 8
The Cinderella Cottage Oak Bluffs
The Cinderella Cottage Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach and Steps to Inkwell Beach
Summer:
 $4,500 - $11,000/wk
Off Season:
 $1,000 - $2,000/night
 $8,000/wk
5
Oak Bluffs
ID 36518
3 BR
2 baths
Sleeps 8
East Chop Waterview - Delightful Contemporary
East Chop Waterview - Delightful Contemporary
Distance to beach: 0.9 mi to The Jetty Beach
OWNER SPECIAL:
PRIME SUMMER WEEKS AVAILABLE luxurious homes reduced prices call now.
Summer:
 $6,500 - $8,000/wk
Off Season:
 $8,000/wk
Oak Bluffs
ID 31215
3 BR
2 baths
Sleeps 8
Happy house 0.5mi Nancy’s & Jetty Beach: 1 2025 wk left!
Happy house 0.5mi Nancy’s & Jetty Beach: 1 2025 wk left!
Distance to beach: 1/2 Mile - Jetty beach on East Chop
5.01 review
Summer:
 $2,800 - $5,500/wk
Off Season:
 $350/night
 $2,800 - $3,500/wk
Oak Bluffs
ID 38157
3 BR
2 baths
Sleeps 8
Endless Summer Vacation
Endless Summer Vacation
Distance to beach: 0.7 mi to The Jetty Beach and 1 mile to Inkwell Beach
5.05 reviews
Summer:
 $5,000 - $7,500/wk
Off Season:
 $500 - $1,000/night
 $3,500 - $4,500/wk
Lagoon
ID 38690
3 BR
2 ½ baths
Sleeps 8
Waterfront Home with Jacuzzi in Vineyard Haven
Waterfront Home with Jacuzzi in Vineyard Haven
Distance to beach: 2.4 mi Oak Bluffs Town Beach and 100 ft to Private beach downhill on a path
Summer:
 $6,608 - $11,000/wk
Oak Bluffs
ID 39654
3 BR
2 baths
Sleeps 8
NOBLE HOUSE: Charming Oasis Near Town & Beach
NOBLE HOUSE: Charming Oasis Near Town & Beach
Distance to beach: 1.2 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $6,000/wk
 $28,000 - $32,000/mo
Off Season:
 $1,000 - $5,500/wk
 $3,500 - $20,000/mo
3
Oak Bluffs
ID 39627
3 BR
2 baths
Sleeps 8
Waterview Farm w/ Kayaks and Paddleboards
Waterview Farm w/ Kayaks and Paddleboards
Distance to beach: 2.4 mi to Oak Bluffs Town Beach and Association beach on Sengekontacket Pond
Summer:
 $3,500 - $6,000/wk
Off Season:
 $2,800 - $3,500/wk
Central Oak Bluffs
ID 39959
3 BR
3 baths
Sleeps 8
Charming Farmhouse with Central A/C Close to Town
Charming Farmhouse with Central A/C Close to Town
Distance to beach: 1.1 mi to The Jetty Beach
Summer:
 $4,200 - $4,600/wk
Off Season:
 $500 - $700/night
 $3,500 - $4,000/wk
Oak Bluffs
ID 30436
3 BR
2 ½ baths
Sleeps 8
Delightful 3 Bedroom ~ Sleeps 8 ~ Close to Town & Lagoon
Delightful 3 Bedroom ~ Sleeps 8 ~ Close to Town & Lagoon
Distance to beach: 3+ miles to Eastville Beach
OWNER SPECIAL:
August 10th last available week!
Summer:
 $5,600/wk
Oak Bluffs
ID 31356
3 BR
4 ½ baths
Sleeps 8
Ellen’s Quintessential Cape w/ Tennis/Bike Path
Ellen’s Quintessential Cape w/ Tennis/Bike Path
Distance to beach: 3.8 mi to Oak Bluffs Town Beach and 4.0 mi to State Beach (Joseph Sylvia State Beach)
5 reviews
Summer:
 $5,200 - $7,400/wk
Off Season:
 $575 - $850/night
 $3,500 - $7,400/wk
6
Oak Bluffs
ID 40323
3 BR
2 baths
Sleeps 8
Chic Coastal Escape - The Retreat at Towanticut
Chic Coastal Escape - The Retreat at Towanticut
Distance to beach: 1.0 mi to The Jetty Beach
5.01 review
Summer:
 $6,000 - $7,400/wk
Off Season:
 $575 - $1,000/night
 $4,000 - $5,000/wk
4
Oak Bluffs
ID 40322
3 BR
3 baths
Sleeps 8
Sunny, Spacious Oak Bluffs Retreat with Beautiful Yard
Sunny, Spacious Oak Bluffs Retreat with Beautiful Yard
Distance to beach: 2.7 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Save on Lodging Tax!! A/C; Desirable Neighborhood; Minutes to Downtown.
Summer:
 $6,500 - $7,000/wk
3
Oak Bluffs
ID 40517
3 BR
1 ½ bath
Sleeps 8
Oak Bluffs Harbor View/Walk to Beach and Town
Oak Bluffs Harbor View/Walk to Beach and Town
Distance to beach: 0.4 mi to Oak Bluffs Town Beach
Summer:
 $635 - $799/night
 $6,100 - $12,133/wk
Off Season:
 $12,100/wk
2
Oak Bluffs
ID 40586
3 BR
2 ½ baths
Sleeps 8
Newly Renovated 3 bedroom 2.5 Bath Home with Harbor views!!
Newly Renovated 3 bedroom 2.5 Bath Home with Harbor views!!
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
NEW LISTING IN-TOWN OAK BLUFFS AVAILABLE ALL OF JULY AND SEPTEMBER!
Summer:
 $6,500 - $12,000/wk
Off Season:
 $4,800 - $7,000/wk

Oak Bluffs vacation rentals that sleep 7
Oak Bluffs
ID 6969
4 BR
2 ½ baths
Sleeps 7
Hillside Harborview
Hillside Harborview
Distance to beach: 3/10th of a mile Oak Bluffs Town Beach and 3/10 of a mile to East Chop Beach
5.02 reviews
Summer:
 $2,200 - $4,300/wk
Off Season:
 $2,200/wk
East Chop
ID 35529
4 BR
1 ½ bath
Sleeps 7
Quiet, Comfy Home in Heart of East Chop - walk to the beach!
Quiet, Comfy Home in Heart of East Chop - walk to the beach!
Distance to beach: 0.5 mi to The Jetty Beach
4.97 reviews
Summer:
 $3,500 - $5,000/wk
 $15,000 - $16,000/mo
Off Season:
 $3,000 - $3,900/wk
3
Oak Bluffs
ID 35901
4 BR
1 ½ bath
Sleeps 7
Oak Bluffs Charmer
Oak Bluffs Charmer
Distance to beach: 0.9 mi to Oak Bluffs Town Beach
Summer:
 $400 - $600/night
 $3,000 - $3,600/wk
Off Season:
 $400 - $600/night
 $3,000 - $3,600/wk
Oak Bluffs
ID 21147
3 BR
2 baths
Sleeps 7
Oak Bluffs ''Quaint Victorian Home''
Oak Bluffs ''Quaint Victorian Home''
Distance to beach: One and a quarter mile State Beach and 1/4 mile, Eastville--1 1/2 Oak Bluffs town beach
4.54 reviews
Summer:
 $2,500 - $3,800/wk
 $10,000 - $11,000/mo
Off Season:
 $350 - $500/night
 $2,400 - $3,000/wk
 $9,000 - $10,000/mo
5
Historic Copeland District/ In
ID 28831
3 BR
2 ½ baths
Sleeps 7
Perfect! 7 houses from the Beach-Walk to Ferry & Town!
Perfect! 7 houses from the Beach-Walk to Ferry & Town!
Distance to beach: 500 ft to Town Beach, Inkwell, State Beach
5.02 reviews
LAST MINUTE ALERT 7/20 - 7/27
OWNER SPECIAL:
***REDUCED*** $5,500 (Wk/of 7/20) Last minute cancellation ($2,000 savings)!
Summer:
 $5,000 - $9,000/wk
Off Season:
 $3,000 - $5,000/wk
Oak Bluffs
ID 33550
3 BR
3 baths
Sleeps 7
Our great Guest Review's tell it all!
Our great Guest Review's tell it all!
Distance to beach: 2 miles Oak Bluffs Town Beach and 1.5 Eastville Beach
5.026 reviews
OWNER SPECIAL:
Remaining weeks offered at $6000 for last minute plans!
Summer:
 $6,000 - $7,500/wk
Off Season:
 $5,500 - $6,000/wk
7
Oak Bluffs
ID 39731
3 BR
2 baths
Sleeps 7
Charming Apartment w/ Privacy in Great Location
Charming Apartment w/ Privacy in Great Location
Distance to beach: 1.8 mi to Oak Bluffs Town Beach
Summer:
 $5,000 - $6,800/wk
Off Season:
 $750 - $975/night
 $5,000 - $6,000/wk
2
Vineyard Hills
ID 39962
3 BR
2 ½ baths
Sleeps 7
Oak Bluffs Escape - Close to Town and Beaches!
Oak Bluffs Escape - Close to Town and Beaches!
Distance to beach: 2.7 mi to Oak Bluffs Town Beach
3 reviews
OWNER SPECIAL:
New Listing: 10% off your weekly rental (through Sept. 28, 2025) if booked by Aug. 4, 2025.
Summer:
 $555 - $965/night
 $4,305 - $6,750/wk
Off Season:
 $349 - $850/night
 $2,443 - $5,750/wk
Oak Bluffs
ID 6897
3 BR
1 ½ bath
Sleeps 7
Comfortable Cape within walking distance to Downtown
Comfortable Cape within walking distance to Downtown
Distance to beach: 8/10 miles to Oak Bluffs Town Beach
4.69 reviews
Summer:
 $3,200/wk
Off Season:
 $2,800/wk
Historic Downtown Copeland Dis
ID 13640
3 BR
2 ½ baths
Sleeps 7
Lovely In-town Victorian ~ walk to beach & ferry
Lovely In-town Victorian ~ walk to beach & ferry
Distance to beach: 2.5 blocks to Oak Bluffs Town Beach and the Inkwell
4.915 reviews
Summer:
 $3,600 - $4,000/wk
Off Season:
 $3,100 - $3,400/wk
6
Oak Bluffs-MCVMA
ID 35732
3 BR
1 ½ bath
Sleeps 7
OB Harbor-Front Ginger-Bread Cottage ''Tight Squeeze''
OB Harbor-Front Ginger-Bread Cottage ''Tight Squeeze''
Distance to beach: 4/10 mi to Oak Bluffs Town Beach and 5/10 mi to The Jetty Beach
4.86 reviews
Summer:
 $4,950 - $6,995/wk
Off Season:
 $4,950 - $5,900/wk
4
Oak Bluffs
ID 35306
3 BR
2 baths
Sleeps 7
Escape the ordinary, Perfect getaway for all ages Book now !
Escape the ordinary, Perfect getaway for all ages Book now !
Distance to beach: 2.4 mi to Oak Bluffs Town Beach and your own Private Beach on Lagoon Pond
4.01 review
OWNER SPECIAL:
GREAT WEEKS OPEN, ALL OF JUNE, WEEK OF JULY 4TH, & 24TH.
Summer:
 $7,000 - $10,000/wk
Off Season:
 $6,000 - $6,500/wk
Oak Bluffs
ID 28887
2 BR
1 ½ bath
Sleeps 7
2+BR ''Gingerbread'' Cottage - Walk to ALL!
2+BR ''Gingerbread'' Cottage - Walk to ALL!
Distance to beach: 10 minute walk to Oak Bluffs Town Beach and 10 minute walk to The Jetty Beach
4.914 reviews
OWNER SPECIAL:
$600.off listed price of any available week in July!! Walking distance from OB Ferry terminal.
Summer:
 $3,700 - $5,200/wk
Off Season:
 $2,000 - $3,600/wk
 $2,000/mo
3
Oak Bluffs
ID 39425
2 BR
2 baths
Sleeps 7
Oceanfront on OB Lagoon; Direct Access to Beach; 2 Moorings
Oceanfront on OB Lagoon; Direct Access to Beach; 2 Moorings
Distance to beach: On Oak Bluffs Lagoon
Summer:
 $8,000 - $10,000/wk
Off Season:
 $7,000 - $9,500/wk
4

Oak Bluffs vacation rentals that sleep 6
Harthaven
ID 33945
6 BR
1 ½ bath
Sleeps 6
Harthaven 4 Bedroom Cottage, AC, Assn Beach and Tennis
Harthaven 4 Bedroom Cottage, AC, Assn Beach and Tennis
Distance to beach: 1 mile Oak Bluffs Town Beach and 2/10th of a mile to Harthaven Association Beach
OWNER SPECIAL:
Open the Weeks of 8/9 and 8/16 due to cancelation.
Summer:
 $6,000 - $6,900/wk
Oak Bluffs
ID 31734
4 BR
1 ½ bath
Sleeps 6
4 Bedroom Gingerbread Cottage on Oak Bluffs Harbor
4 Bedroom Gingerbread Cottage on Oak Bluffs Harbor
Distance to beach: 2-3 blocks to the Inkwell Town Beach
5.01 review
LAST MINUTE ALERT 7/26 - 8/2
OWNER SPECIAL:
July price reduction.
Summer:
 $4,000 - $6,000/wk
Off Season:
 $4,000/wk
4
Oak Bluffs
ID 29086
4 BR
2 baths
Sleeps 6
Quaint Historic Cottage: Walk to Beach, Harbor, Circuit Ave
Quaint Historic Cottage: Walk to Beach, Harbor, Circuit Ave
Distance to beach: 1/4 mile The Jetty Beach and 1/2 mile Oak Bluffs Town Beach
5.03 reviews
OWNER SPECIAL:
Discounted rate. Aug 9-16. $8700.00.
Summer:
 $5,000 - $9,700/wk
 $38,000 - $39,000/mo
Off Season:
 $5,000 - $7,500/wk
 $20,000/mo
3
Oak Bluffs
ID 9098
3 BR
2 baths
Sleeps 6
Waterfront Cottage on Oak Bluffs Harbor w/ Small Beach!
Waterfront Cottage on Oak Bluffs Harbor w/ Small Beach!
Distance to beach: 5 min walk The Jetty Beach and On harbor w/sandy beach; 5 min walk to ocean beach
5.015 reviews
Summer:
 $5,250 - $7,875/wk
Off Season:
 $4,900 - $5,250/wk
Oak Bluffs
ID 9553
3 BR
2 baths
Sleeps 6
Oak Bluffs Family Vacation Home
Oak Bluffs Family Vacation Home
Distance to beach: Lagoon Eastville Beach and 3 miles State Beach (Joseph Sylvia State Beach)
5.03 reviews
Summer:
 $600 - $900/night
 $2,500 - $3,800/wk
 $14,000 - $16,000/mo
Off Season:
 $400 - $500/night
 $1,500 - $3,500/wk
 $2,000 - $6,000/mo
10
Oak Bluffs
ID 9028
3 BR
2 ½ baths
Sleeps 6
Vineyard Retreat - The perfect place for rest and relaxation
Vineyard Retreat - The perfect place for rest and relaxation
Distance to beach: 2.5 miles State Beach and 2/10 mile to a beach on a large 3,968 acre pond
4.816 reviews
Summer:
 $3,600 - $4,600/wk
 $14,000 - $16,000/mo
Off Season:
 $3,000 - $3,900/wk
 $11,000 - $15,000/mo
4
Oak Bluffs
ID 12452
3 BR
1 ½ bath
Sleeps 6
Easy and comfortable Island home
Easy and comfortable Island home
Distance to beach: 1/4 mile Eastville Beach and 1/2 mile to Jetty Beach
4.97 reviews
Summer:
 $3,400 - $4,000/wk
Off Season:
 $375 - $600/night
 $2,600 - $3,400/wk
5
Sea View Ave. just out of town
ID 19701
3 BR
2 baths
Sleeps 6
Charming 1800's Victorian Cottage Fronting the Sound
Charming 1800's Victorian Cottage Fronting the Sound
Distance to beach: 500 feet to inkwell beach
4.711 reviews
OWNER SPECIAL:
$500 off list price for each remaining week!
Summer:
 $3,800 - $5,200/wk
Off Season:
 $4,000 - $4,500/wk
2
Oak Bluffs
ID 22799
3 BR
3 baths
Sleeps 6
MV Peace of Pie - Short 15 min walk to OB center, AC
MV Peace of Pie - Short 15 min walk to OB center, AC
Distance to beach: 1.1 miles to Oak Bluffs Town Beach
5.015 reviews
Summer:
 $5,000 - $6,500/wk
Off Season:
 $4,500 - $5,000/wk
Oak Bluffs Lagoon Pond area
ID 23542
3 BR
2 baths
Sleeps 6
Contemporary 3 BR Just 300 Yds from the Lagoon in Oak Bluffs
Contemporary 3 BR Just 300 Yds from the Lagoon in Oak Bluffs
Distance to beach: Lagoon Beach 1/2 mile, Eastville Beach < 1 mile
4.910 reviews
Summer:
 $3,200 - $3,700/wk
Off Season:
 $3,600/wk
6
Oak Bluffs
ID 20575
3 BR
3 baths
Sleeps 6
Bright Modern House w/ AC-Sleeps 7 Walk to Beach & Shops
Bright Modern House w/ AC-Sleeps 7 Walk to Beach & Shops
Distance to beach: Lagoon Beach-end of block;15 min bike- State Beach
5.02 reviews
Summer:
 $500 - $750/night
 $3,000 - $4,900/wk
 $15,000 - $18,000/mo
Off Season:
 $2,500 - $3,500/wk
 $4,000 - $9,000/mo
Oak Bluffs
ID 24822
3 BR
2 baths
Sleeps 6
Pristine Retreat - Blue Stone Patio - Fire Pit
Pristine Retreat - Blue Stone Patio - Fire Pit
Distance to beach: 3 miles Oak Bluffs Town Beach and Less than 2 miles to Sailing Camp Park
5.028 reviews
Summer:
 $5,600 - $7,400/wk
Off Season:
 $4,200 - $7,400/wk
6
Oak Bluffs
ID 19888
3 BR
3 baths
Sleeps 6
Beautiful Sunny w/Lagoon View-Walk to Center of Oak Bluffs
Beautiful Sunny w/Lagoon View-Walk to Center of Oak Bluffs
Distance to beach: 130 feet (steps) from the house
5.05 reviews
Summer:
 $2,100 - $3,600/wk
 $2,650 - $13,000/mo
Off Season:
 $1,950 - $2,600/wk
 $1,950 - $9,000/mo
Oak Bluffs
ID 32157
3 BR
2 baths
Sleeps 6
Charming Home On Farm Pond w/ Ocean View walk to Inkwell
Charming Home On Farm Pond w/ Ocean View walk to Inkwell
Distance to beach: 4/10 mile to Inkwell Beach
1 review
Summer:
 $3,750 - $4,675/wk
Off Season:
 $2,500 - $3,675/wk
2
Oak Bluffs
ID 33125
3 BR
2 baths
Sleeps 6
Cozy Sunlit Cottage, quick walk to downtown Oak Bluffs!
Cozy Sunlit Cottage, quick walk to downtown Oak Bluffs!
Distance to beach: 1 mile To Oak Bluffs Town Beach
5.06 reviews
Summer:
 $2,800 - $3,300/wk
Off Season:
 $2,800/wk
Near MV Hospital
ID 33461
3 BR
1 bath
Sleeps 6
Flexible start/end dates. 7 min nights .New living room furn
Flexible start/end dates. 7 min nights .New living room furn
Distance to beach: 7/10 mi to The Jetty Beach and 1/2 mi to Eastville Beach
Summer:
 $2,650 - $3,150/wk
Off Season:
 $2,450 - $3,150/wk
East Chop
ID 32946
3 BR
2 baths
Sleeps 6
Newly Renovated East Chop Home. Walk to beach and town!
Newly Renovated East Chop Home. Walk to beach and town!
Distance to beach: 3/10 mi To The Jetty Beach
5.017 reviews
Summer:
 $4,500 - $5,250/wk
Off Season:
 $3,500 - $4,000/wk
5
Walk to town- quiet location
ID 33701
3 BR
2 baths
Sleeps 6
Quiet Oak Bluffs Neighborhood walk to Harbor, Beach,Village
Quiet Oak Bluffs Neighborhood walk to Harbor, Beach,Village
Distance to beach: 6/10 mi to The Jetty Beach and 1 mi Oak Bluffs Town Beach
OWNER SPECIAL:
Drastic discounts (shown in pricing).
Summer:
 $3,000 - $3,800/wk
Off Season:
 $3,000 - $3,300/wk
 $2,500 - $3,000/mo
Oak Bluffs
ID 34172
3 BR
2 ½ baths
Sleeps 6
Vineyard Get-Away
Vineyard Get-Away
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
5.012 reviews
Summer:
 $3,650 - $6,500/wk
Off Season:
 $600 - $625/night
 $3,500 - $4,000/wk
3
Oak Bluffs
ID 34492
3 BR
2 ½ baths
Sleeps 6
Heated saltwater pool, stunning sunsets, 2 kayaks!
Heated saltwater pool, stunning sunsets, 2 kayaks!
Distance to beach: 1/4 mi to Lagoon Pond Public Beach Oak Bluffs Town Beach
5.021 reviews
OWNER SPECIAL:
Only one summer week left! 7/20 to 7/27.
Summer:
 $8,600 - $11,600/wk
Off Season:
 $6,500 - $7,900/wk
 $17,000/mo
5
Oak Bluffs
ID 35638
3 BR
2 ½ baths
Sleeps 6
Modern Gingerbread Home, 3 Min Walk to Lagoon
Modern Gingerbread Home, 3 Min Walk to Lagoon
Distance to beach: 1.5 mi to Oak Bluffs Town Beach and 1.0 mi to Eastville Beach
Summer:
 $4,500 - $7,000/wk
5
Oak Bluffs
ID 36742
3 BR
2 baths
Sleeps 6
Beautiful Inground Pool, Ferry tickets avail
Beautiful Inground Pool, Ferry tickets avail
Distance to beach: 4.4 miles Oak Bluffs Town Beach
5.01 review
Summer:
 $4,300 - $6,500/wk
Off Season:
 $2,000 - $5,700/wk
Lagoon Heights
ID 36917
3 BR
2 baths
Sleeps 6
Cozy Cape near Lagoon
Cozy Cape near Lagoon
Distance to beach: 3 Blocks Walking distance to Lagoon
Summer:
 $4,500 - $5,000/wk
Off Season:
 $575 - $700/night
 $3,500 - $5,000/wk
3
Oak Bluffs
ID 37210
3 BR
1 bath
Sleeps 6
Birds of Paradise - Walk to Beaches and Town
Birds of Paradise - Walk to Beaches and Town
Distance to beach: 1/2 mi to Oak Bluffs Town Beach
Summer:
 $3,000 - $4,500/wk
Off Season:
 $2,500 - $4,500/wk
2
Oak Bluffs
ID 37557
3 BR
2 ½ baths
Sleeps 6
Pristine Home in Oak Bluffs/Close to Downtown
Pristine Home in Oak Bluffs/Close to Downtown
Distance to beach: 1 mi to Eastville Beach and 1.2 mi to Inkwell Beach
5.03 reviews
Summer:
 $7,000 - $9,990/wk
Off Season:
 $3,100 - $8,600/wk
Oak Bluffs
ID 37961
3 BR
2 baths
Sleeps 6
Beautiful Home / Walk to Town
Beautiful Home / Walk to Town
Distance to beach: 1.0 mi to Oak Bluffs Town Beach
LAST MINUTE ALERT 7/5 - 7/12
OWNER SPECIAL:
$40 Gift certificate for Mad Martha's ice cream.
Summer:
 $425/night
 $3,000 - $7,225/wk
 $12,000 - $16,000/mo
Off Season:
 $320/night
 $2,500 - $5,500/wk
 $10,000 - $16,000/mo
Gingerbred Cottages - MVCMA
ID 38584
3 BR
1 ½ bath
Sleeps 6
Beautifully Updated Gingerbread Family Cottage Walk to Town
Beautifully Updated Gingerbread Family Cottage Walk to Town
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
Summer:
 $5,250 - $5,500/wk
Off Season:
 $5,250/wk
5
Oak Bluffs
ID 38623
3 BR
1 bath
Sleeps 6
Dottie's House - HIstoric Home in the Heart of Oak Bluffs
Dottie's House - HIstoric Home in the Heart of Oak Bluffs
Distance to beach: 1/2 mi to The Jetty Beach and 1.2 mi to Oak Bluffs Town Beach
5.04 reviews
LAST MINUTE ALERT 7/13 - 7/20
OWNER SPECIAL:
Three night minimum and price reduced!
Summer:
 $3,300 - $5,500/wk
Off Season:
 $3,150 - $4,200/wk
Oak Bluffs
ID 39435
3 BR
1 ½ bath
Sleeps 6
Updated Home, Steps to Town/Ferry, Beach, Ocean Views
Updated Home, Steps to Town/Ferry, Beach, Ocean Views
Distance to beach: 300 yards Oak Bluffs Town Beach
4.55 reviews
Summer:
 $6,000 - $8,500/wk
Off Season:
 $300 - $600/night
 $2,100 - $7,000/wk
2
Oak Bluffs
ID 39483
3 BR
2 baths
Sleeps 6
Top Notch Vacation Rentals (Walk to Sengekontacket Pond)
Top Notch Vacation Rentals (Walk to Sengekontacket Pond)
Distance to beach: 1 mi to Oak Bluffs Town Beach and 5 min walk to Sengekontacket Pond
Summer:
 $5,000/wk
Off Season:
 $650 - $700/night
 $2,500 - $3,000/wk
Oak Bluffs
ID 39601
3 BR
2 baths
Sleeps 6
Ferry tickets- close to town and beachesOak Bluffs
Ferry tickets- close to town and beachesOak Bluffs
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
4th of July week available.
Summer:
 $2,000 - $2,200/night
 $4,500 - $8,000/wk
Off Season:
 $4,500/wk
4
Oak Bluffs - East Chop
ID 39616
3 BR
3 baths
Sleeps 6
Oak Bluffs/East Chop Modern Retreat w/ Detached Studio!
Oak Bluffs/East Chop Modern Retreat w/ Detached Studio!
Distance to beach: 1 mi Oak Bluffs Town Beach and 1.2 mi to Eastville Beach
5.01 review
OWNER SPECIAL:
Price drop of $250 for week of July 26 - August 2. Was $4,500 now $4,250.
Summer:
 $3,500 - $5,000/wk
Off Season:
 $1,500 - $3,000/wk
11
East Chop
ID 39481
3 BR
2 baths
Sleeps 6
East Chop Oasis/Newly Renovated- Walk to Town
East Chop Oasis/Newly Renovated- Walk to Town
Distance to beach: 0.8 mi to The Jetty Beach
Summer:
 $5,000 - $7,000/wk
Off Season:
 $500 - $740/night
 $4,400 - $5,200/wk
2
Oak Bluffs
ID 40082
3 BR
2 baths
Sleeps 6
Chic Designer Hideaway, Stroll to Oak Bluffs Harbor
Chic Designer Hideaway, Stroll to Oak Bluffs Harbor
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
Summer:
 $7,000 - $8,000/wk
Off Season:
 $3,500/wk
Oak Bluffs
ID 40326
3 BR
1 bath
Sleeps 6
Vineyard Charm Pet Friendly!
Vineyard Charm Pet Friendly!
Distance to beach: 0.4 mi to The Jetty Beach
OWNER SPECIAL:
AUGUST DATES STILL OPEN * PET FRIENDLY.
Summer:
 $4,500 - $5,000/wk
Off Season:
 $500 - $800/night
 $3,500 - $4,000/wk
1
Oak Bluffs
ID 39958
3 BR
1 ½ bath
Sleeps 6
MV Starhouse
MV Starhouse
Distance to beach: 1.8 mi to Oak Bluffs Town Beach and Very close to Sailing Camp on the lagoon.
OWNER SPECIAL:
Just Listed - July weeks now available.
Summer:
 $1,900 - $2,500/wk
Off Season:
 $175 - $250/night
 $1,800 - $1,900/wk
Oak Bluffs
ID 40097
3 BR
2 baths
Sleeps 6
Beautiful and Remodeled in Prime Location
Beautiful and Remodeled in Prime Location
Distance to beach: 2.1 mi to Oak Bluffs Town Beach
Summer:
 $4,000 - $5,500/wk
Off Season:
 $570/night
 $4,000/wk
3
Oak Bluffs
ID 40495
3 BR
2 baths
Sleeps 6
Robree Farm Retreat/Minutes to Town & Ferries; Walk to Beach
Robree Farm Retreat/Minutes to Town & Ferries; Walk to Beach
Distance to beach: 1.2 mi to The Jetty Beach and 2/10 mi to Eastville Beach
Summer:
 $800 - $1,200/night
 $4,200 - $7,700/wk
 $18,000 - $33,000/mo
Off Season:
 $600 - $900/night
 $3,500 - $7,700/wk
 $13,000 - $21,000/mo
3
Oak Bluffs East Chop
ID 40590
3 BR
2 ½ baths
Sleeps 6
East Chop Charmer
East Chop Charmer
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
LAST MINUTE ALERT 7/26 - 8/2
OWNER SPECIAL:
JUST LISTED FOR FAIR, FIREWORKS AND ILLUMINATION WEEK -WALK TO THE TOWN OF OAK BLUFFS.
Summer:
 $6,500 - $12,000/wk
Oak Bluffs
ID 4217
3 BR
2 baths
Sleeps 6
Spectacular 3 bedroom, 2 bath Home Steps from Private Beach
Spectacular 3 bedroom, 2 bath Home Steps from Private Beach
Distance to beach: 2/10 mile to private Lagoon Beach
Summer:
 $4,500 - $7,000/wk
Off Season:
 $450/night
 $3,200 - $5,500/wk
3
Oak Bluffs
ID 35304
3 BR
3 ½ baths
Sleeps 6
LOVELY 3 BR, CENTRAL AC, MEDIA & GAME ROOM, LAGOON
LOVELY 3 BR, CENTRAL AC, MEDIA & GAME ROOM, LAGOON
Distance to beach: 1.9 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
We still have great weeks in July call us soon !
Summer:
 $7,500 - $9,500/wk
Off Season:
 $7,500 - $8,500/wk
Oak Bluffs
ID 34548
3 BR
2 baths
Sleeps 6
Jupiter House: Recently Renovated, Open-concept 3 BR Home
Jupiter House: Recently Renovated, Open-concept 3 BR Home
Distance to beach: 1.5 miles to Oak Bluffs Town Beach and 0.5 miles to Eastville Beach
5.03 reviews
Summer:
 $3,000 - $4,700/wk
Off Season:
 $500/night
 $3,000 - $3,200/wk
8
Oak Bluffs
ID 34650
3 BR
2 baths
Sleeps 6
PRIVATE BEACH, SPACIOUS 3 BR, LAGOON VIEWS, BOOK NOW!
PRIVATE BEACH, SPACIOUS 3 BR, LAGOON VIEWS, BOOK NOW!
Distance to beach: 1.6 miles Oak Bluffs Town Beach and
Summer:
 $8,200 - $9,000/wk
Off Season:
 $8,200/wk
Oak Bluffs
ID 37987
3 BR
2 baths
Sleeps 6
Renovated Cottage in Convenient Location to Beaches and Town
Renovated Cottage in Convenient Location to Beaches and Town
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
5.01 review
Summer:
 $650 - $750/night
 $3,000 - $3,500/wk
Off Season:
 $300 - $400/night
 $2,500 - $3,500/wk
Oak Bluffs
ID 35664
3 BR
3 baths
Sleeps 6
Perfect Family House - Walk to Lagoon
Perfect Family House - Walk to Lagoon
Distance to beach: 2 blks to Lagoon Pond;1mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
 $3,000 - $5,000/wk
Off Season:
 $500/night
 $2,000 - $4,000/wk
2
Oak Bluffs
ID 33380
3 BR
1 ½ bath
Sleeps 6
Irresistible Beach House - The Perfect Vacation Escape
Irresistible Beach House - The Perfect Vacation Escape
Distance to beach: 1.6 mi to Oak Bluffs Town Beach
Summer:
 $3,000 - $3,500/wk
Off Season:
 $3,000 - $3,200/wk
Oak Bluffs
ID 22568
2 BR
2 baths
Sleeps 6
Charming two bedroom house near golf course and bike path
Charming two bedroom house near golf course and bike path
Distance to beach: 1 mile to Inkwell and Town Beaches
5.03 reviews
Summer:
 $2,500 - $4,000/wk
 $15,000/mo
Off Season:
 $2,500 - $3,000/wk
9
Oak Bluffs
ID 27087
2 BR
1 bath
Sleeps 6
Oak Bluffs Getaway
Oak Bluffs Getaway
Distance to beach: Lagoon
OWNER SPECIAL:
7/19-7/26 & 7/26-8/2. Price drop due to late availability. $1850 for 7/19 and $1900 for 7/26.
Summer:
 $1,850 - $1,900/wk
Off Season:
 $1,500/wk
Oak Bluffs
ID 33919
2 BR
2 ½ baths
Sleeps 6
Oak Bluffs Retreat - The perfect getaway!
Oak Bluffs Retreat - The perfect getaway!
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
 $3,325 - $4,655/wk
Off Season:
 $390 - $545/night
 $3,255 - $3,990/wk
In-Town of Oak Bluffs
ID 36162
2 BR
3 ½ baths
Sleeps 6
Charming Cottage in Great OB Location
Charming Cottage in Great OB Location
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
Summer:
 $5,000 - $6,000/wk
Off Season:
 $500 - $1,000/night
 $5,000/wk
3

Oak Bluffs vacation rentals that sleep 5
Oak Bluffs
ID 16588
3 BR
1 ½ bath
Sleeps 5
Vanessa's Hide-Away; ferry res. avail. 7/29-8/5
Vanessa's Hide-Away; ferry res. avail. 7/29-8/5
Distance to beach: 2 minute walk to Oak Bluffs Beaches
5.07 reviews
OWNER SPECIAL:
20% off July weeks! 2 blocks from Inkwell Beach/water views/walk to town. 7/26-8/2 ferry res. avail!
Summer:
 $3,795 - $4,795/wk
Off Season:
 $3,595 - $4,295/wk
Oak Bluffs
ID 21790
3 BR
1 ½ bath
Sleeps 5
Ideal location, short walk to Town & Beach, 3 night min Sept
Ideal location, short walk to Town & Beach, 3 night min Sept
Distance to beach: 7 min walk Oak Bluffs Town Beach and 7-minute walk to Inkwell Beach
5.010 reviews
OWNER SPECIAL:
late Aug&Sep discounted! Location, Location!
Summer:
 $2,695 - $4,495/wk
Off Season:
 $480/night
 $2,100 - $3,495/wk
Oak Bluffs
ID 40039
3 BR
2 baths
Sleeps 5
Oak Bluffs Property 8000
Oak Bluffs Property 8000
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
Summer:
 $3,000 - $6,000/wk
Oak Bluffs
ID 36583
2 BR
2 baths
Sleeps 5
Cozy-Cottage-Glam off Circuit Great Outdoor Living.2Bd/2B
Cozy-Cottage-Glam off Circuit Great Outdoor Living.2Bd/2B
Distance to beach: 4/10 mi to Inkwell Oak Bluffs Town Beach
5.02 reviews
Summer:
 $750 - $925/night
 $6,000 - $7,500/wk
Off Season:
 $500/night
 $3,500 - $6,500/wk
Oak Bluffs
ID 39869
2 BR
2 baths
Sleeps 5
Seaview condo
Seaview condo
Distance to beach: 0.1 mi to Oak Bluffs Town Beach
Summer:
 $5,500/wk
 $22,000 - $27,500/mo
Off Season:
 $4,500 - $5,500/wk
 $18,000 - $22,500/mo
Oak Bluffs
ID 40351
2 BR
1 bath
Sleeps 5
Oak Bluffs 2 Bedroom Sleeps 5 - Less than a Mile to Town
Oak Bluffs 2 Bedroom Sleeps 5 - Less than a Mile to Town
Distance to beach: 1.6 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
NEW LISTING! OPEN AVAILABILITY!
Summer:
 $3,500 - $4,500/wk
Off Season:
 $3,000 - $3,500/wk
Oak Bluffs
ID 40289
2 BR
2 baths
Sleeps 5
Oak Bluffs 2 Bedroom Sleeps 5 Available All of August 2025!
Oak Bluffs 2 Bedroom Sleeps 5 Available All of August 2025!
Distance to beach: 0.9 mi to The Jetty Beach
OWNER SPECIAL:
AVAILABLE WEEK OF 7/19 and 7/26/25.
Summer:
 $2,650 - $3,100/wk
Oak Bluffs
ID 10417
2 BR
1 bath
Sleeps 5
Cozy cottage about 700 ft from the Inkwell Beach
Cozy cottage about 700 ft from the Inkwell Beach
Distance to beach: Inkwell/Town Beach Oak Bluffs Town Beach and 700 ft to town beach
5.01 review
Summer:
 $3,000/wk
Off Season:
 $2,300/wk
2

Oak Bluffs vacation rentals that sleep 4
Oak Bluffs
ID 30504
2 BR
1 bath
Sleeps 4
OAK BLUFFS GETAWAY
OAK BLUFFS GETAWAY
Distance to beach: 9/10 mile to Inkwell Beach
5.06 reviews
Summer:
 $3,000 - $5,000/wk
Off Season:
 $3,000/wk
3
Oak Bluffs
ID 35127
2 BR
2 ½ baths
Sleeps 4
Charming Cottage Located in Heart of Oak Bluffs
Charming Cottage Located in Heart of Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Cottage located in Heart of Oak Bluffs is open for booking the week of 8/9-8/16.
Summer:
 $4,865 - $8,400/wk
Off Season:
 $2,900 - $5,040/wk
Oak Bluffs on the Edgartown li
ID 37184
2 BR
1 ½ bath
Sleeps 4
Last minute cancellation - August dates available!
Last minute cancellation - August dates available!
Distance to beach: 5.5 miles State Beach and 7 miles South Beach - Katama
5.01 review
OWNER SPECIAL:
Last minute cancellation - August weeks available!
Summer:
 $3,000 - $3,500/wk
 $10,000/mo
Off Season:
 $3,500/wk
 $10,000/mo
East Chop
ID 38085
2 BR
1 bath
Sleeps 4
Gorgeous Water View Cottage with Great Location
Gorgeous Water View Cottage with Great Location
Distance to beach: 0.5 mi to The Jetty Beach and 0.5 mi to Oak Bluffs Town Beach
4.73 reviews
LAST MINUTE ALERT 7/5 - 7/12
OWNER SPECIAL:
Suddenly have two weeks in July open at this fabulous cabin on the bluff! Stay one week or two.
Summer:
 $6,000 - $7,000/wk
Off Season:
 $5,000 - $6,000/wk
7
Oak Bluffs
ID 38849
2 BR
1 bath
Sleeps 4
Oak Bluffs Cottage Walk to Town & Beach
Oak Bluffs Cottage Walk to Town & Beach
Distance to beach: .75 miles The Jetty Beach and 3/4 Mile to The Inkwell Beach
Summer:
 $3,150 - $9,450/wk
Off Season:
 $450/night
 $3,150 - $4,200/wk
Oak Bluffs
ID 39799
2 BR
2 baths
Sleeps 4
Updated Cottage - 7 Minute Walk to Town - Ferry Tickets
Updated Cottage - 7 Minute Walk to Town - Ferry Tickets
Distance to beach: 0.5 mi to Oak Bluffs Town Beach and .05 mi to Inkwell Beach
Summer:
 $3,850 - $9,500/wk
Off Season:
 $3,850/wk
Oak Bluffs
ID 17574
2 BR
1 bath
Sleeps 4
Walk to Sailing Camp Beach – Nature Trails & Serene Backyard
Walk to Sailing Camp Beach – Nature Trails & Serene Backyard
Distance to beach: 200yd to Sailing Camp beach. 2.1m to Inkwell beach
5.03 reviews
LAST MINUTE ALERT 7/5 - 7/12 and 7/12 - 7/19
OWNER SPECIAL:
**Prices Reduced $500/week in July!! Flexible Check in. Walk To Sailing Camp Beach & Walking Trail.
Summer:
 $430 - $550/night
 $3,000 - $3,850/wk
Off Season:
 $450 - $500/night
 $2,800 - $3,850/wk
4
Oak Bluffs
ID 40166
2 BR
1 bath
Sleeps 4
Waterfront Cottage on Private Beach; Amazing Sunsets
Waterfront Cottage on Private Beach; Amazing Sunsets
Distance to beach: On Private Beach; 3/10 mi to Eastville Beach
OWNER SPECIAL:
$2500 for the week - enjoy 4th of July on the Vineyard- Waterfront Cottage.
Summer:
 $2,500 - $3,500/wk
Off Season:
 $1,000 - $3,500/wk
 $1,900 - $3,000/mo
East Chop (Oak Bluffs)
ID 4096
1 BR
1 bath
Sleeps 4
Beautiful Cottage Retreat: Reminiscent of Summer Traditions
Beautiful Cottage Retreat: Reminiscent of Summer Traditions
Distance to beach: 2/10 mile to Oak Buffs Harbor/Marina Beach
5.03 reviews
Summer:
 $10,000/mo
Off Season:
 $10,000/mo

Oak Bluffs vacation rentals that sleep 3
Oak Bluffs
ID 23427
2 BR
1 bath
Sleeps 3
Huckleberry Lodge ...Adorable Island Cottage
Huckleberry Lodge ...Adorable Island Cottage
Distance to beach: 3 miles State Beach
5.09 reviews
Summer:
 $2,100/wk
Off Season:
 $250 - $275/night
 $1,750 - $2,100/wk
6
Oak Bluffs
ID 34370
2 BR
1 bath
Sleeps 3
Absolutely Amazing... Lovely, Cozy Garden Cottage
Absolutely Amazing... Lovely, Cozy Garden Cottage
Distance to beach: 9/10 mi to The Jetty Beach
Summer:
 $5,500 - $6,500/night
 $15,000 - $20,000/mo
Off Season:
 $4,500 - $5,500/night
 $10,000 - $20,000/mo
4
Oak Bluffs
ID 21977
1 BR
1 bath
Sleeps 3
Wooded Haven, Martha's Vineyard Oasis
Wooded Haven, Martha's Vineyard Oasis
Distance to beach: 1.5 miles to Oak Bluffs Town Beach and 5/10 mile to Eastville Beach
4.518 reviews
Summer:
 $2,800 - $3,000/wk
 $10,000 - $12,000/mo
Off Season:
 $2,100 - $2,600/wk
 $1,500 - $1,800/mo
4
Oak Bluffs
ID 34153
1 BR
1 bath
Sleeps 3
Perfect One Bedroom Garage Apartment w/AC
Perfect One Bedroom Garage Apartment w/AC
Distance to beach: 1.1 mi to The Jetty Beach and 1.3 to Inkwell Beach
5.07 reviews
Summer:
 $1,500 - $2,500/wk
Off Season:
 $1,500/wk
3

Oak Bluffs vacation rentals that sleep 2
Oak Bluffs
ID 11609
1 BR
1 ½ bath
Sleeps 2
Sweet Pea Cottage, Walk To Beach
Sweet Pea Cottage, Walk To Beach
Distance to beach: 1/10 mile Oak Bluffs Town Beach
69 reviews
Summer:
 $2,250 - $3,400/wk
 $13,000 - $14,000/mo
Off Season:
 $350 - $450/night
 $1,850 - $3,200/wk
 $3,600 - $6,800/mo
Oak Bluffs
ID 32208
1 BR
1 bath
Sleeps 2
''The Nest'' Guest House: Steps to Beach/town, Water Views!
''The Nest'' Guest House: Steps to Beach/town, Water Views!
Distance to beach: 1/10 of a mile to Oak Bluffs Town Beach and a short bike ride on the path State Beach
5.08 reviews
OWNER SPECIAL:
More flexible dates in shoulder season (end of August, Sept).
Summer:
 $350 - $600/night
 $2,900 - $5,200/wk
 $9,000 - $13,000/mo
Off Season:
 $2,100 - $3,500/wk
 $7,000 - $11,800/mo
2
#CozyBluffs
ID 34909
1 BR
1 ½ bath
Sleeps 2
#CozyBluffs - Walk to Beach/Circuit Ave/OB ferries!
#CozyBluffs - Walk to Beach/Circuit Ave/OB ferries!
Distance to beach: 1/2 mi to The Jetty Beach
7 reviews
LAST MINUTE ALERT 7/12 - 7/19
OWNER SPECIAL:
15% off listed rates for stays thru July 18th, 3 night min & flexible arrival/departure dates!
Summer:
 $4,193 - $4,893/wk
Off Season:
 $399 - $699/night
 $2,500 - $4,893/wk
6
Oak Bluffs
ID 40032
1 BR
1 bath
Sleeps 2
Tiny House.... BIG Vacation opportunity
Tiny House.... BIG Vacation opportunity
Distance to beach: 1.4 mi to Oak Bluffs Town Beach and 1/2 mi to Eastville Beach
OWNER SPECIAL:
July Special save $200 on full weeks.
Summer:
 $150 - $300/night
 $2,100 - $2,500/wk
Off Season:
 $150 - $250/night
 $1,900 - $2,100/wk
 $2,400/mo
2