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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 - $35,000/wk
Off Season:
 $2,500 - $4,000/night
 $10,000 - $30,000/wk
 $20,000 - $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 - $8,900/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:
 $15,000 - $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 - $8,000/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
Large Home, Water Views From Porch! Walk to Town and Beach!
Large Home, Water Views From Porch! Walk to Town and Beach!
Distance to beach: 3/10 of a mile, 5 minute walk The Jetty Beach
5.03 reviews
Summer:
 $10,000 - $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
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:
 $14,900 - $20,900/wk
Off Season:
 $11,025/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
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:
 $4,200/wk
Off Season:
 $2,000 - $2,500/night
 $3,500/wk
3
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
Lagoon Pond Salt-Waterfront
ID 27817
4 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
OWNER SPECIAL:
Labor Day week-end week 8/30-9/6. Reduced to $9500! More discount if 8 or <.
Summer:
 $12,000 - $20,000/wk
Off Season:
 $2,000 - $2,500/night
 $6,500 - $14,000/wk
 $25,000 - $30,000/mo
11
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:
 $7,000 - $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
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
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
Soulas Marthas Vineyard Beach House
Soulas Marthas Vineyard Beach House
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 - $35,000/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
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 - $8,132/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 - $19,000/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
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
OWNER SPECIAL:
We are now booking for June 2026 it is time already.
Summer:
 $7,500 - $14,000/wk
Off Season:
 $7,000 - $8,000/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:
 $7,500 - $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 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
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:
 $7,000 - $10,000/wk
Off Season:
 $650 - $800/night
 $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
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
5.011 reviews
Summer:
 $1,000 - $1,450/night
 $6,500 - $11,000/wk
Off Season:
 $850 - $1,000/night
 $6,000 - $8,000/wk
3
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
LAST MINUTE ALERT 7/27 - 8/3
OWNER SPECIAL:
Week of 7/27-8/3 is reduced to $7000 base rate, was $9000. Oak Bluffs w/ 7 min walk to Inkwell Beach
Summer:
 $7,000 - $9,000/wk
Off Season:
 $575 - $1,200/night
 $5,000 - $6,000/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 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:
 $5,500 - $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 - $6,000/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
Exquisite home! central A/C,full-size heated saltwater pool!
Exquisite home! central A/C,full-size heated saltwater pool!
Distance to beach: 1 and 2/10 mile Oak Bluffs Town Beach and 3 miles State Beach
5.09 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
Summer:
 $450 - $500/night
 $3,500 - $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 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 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
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 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:
 $7,500 - $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
5.03 reviews
OWNER SPECIAL:
$500 off listed price for the weeks of July 19th 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:
 $4,000 - $5,700/wk
Off Season:
 $3,000 - $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
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:
 $6,500 - $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 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
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
5.03 reviews
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
ID 40570
3 BR
2 baths
Sleeps 8
Comfortable, Family-Friendly Home w/ Spacious Deck, Fire Pit
Comfortable, Family-Friendly Home w/ Spacious Deck, Fire Pit
Distance to beach: 1 mile The Jetty Beach and 1 mile Eastville Beach
OWNER SPECIAL:
**Just Listed** August Weeks Reduced - See Calendar for Pricing.
Summer:
 $3,600 - $4,000/wk
Off Season:
 $400 - $500/night
 $2,500 - $3,000/wk
5

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
OWNER SPECIAL:
***REDUCED*** last minute cancellation! 7/20 - 7/27 only $5500. Separate cottage available too!
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:
Last week available in Aug reduced (reflected in price)! Walking distance from OB Ferry terminal.
Summer:
 $3,495 - $5,200/wk
Off Season:
 $2,000 - $3,500/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:
 $4,000 - $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:
 $3,000 - $3,500/wk
 $4,000 - $5,000/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:
 $3,300/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
5.013 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
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:
 $5,500/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
Summer:
 $3,500 - $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
4.87 reviews
Summer:
 $6,000 - $8,500/wk
Off Season:
 $400 - $500/night
 $2,800 - $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:
 $3,000 - $5,500/wk
Off Season:
 $700/night
 $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:
 $2,250 - $2,500/wk
Off Season:
 $175 - $250/night
 $1,800/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 40164
3 BR
3 baths
Sleeps 6
Gorgeous Home in Oak Bluffs in Ultra-Convenient Location!
Gorgeous Home in Oak Bluffs in Ultra-Convenient Location!
Distance to beach: 0.5 mi to Oak Bluffs Town Beach and Inkwell Beach
Summer:
 $1,400/night
 $10,000/wk
Off Season:
 $700/night
 $4,900 - $10,000/wk
5
Lagoon Pond Waterfront
ID 40593
3 BR
3 baths
Sleeps 6
Lagoon Waterfront with Amazing Sunset Views
Lagoon Waterfront with Amazing Sunset Views
Distance to beach: Lagoon Pond Waterfront Beach is included
LAST MINUTE ALERT 7/25 - 8/1
OWNER SPECIAL:
**Just Listed** Prices Reduced for Remaining July Weeks; Spectacular Waterfront Retreat!
Summer:
 $7,800 - $8,400/wk
Off Season:
 $6,400 - $8,400/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 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
4.69 reviews
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:
 $4,000 - $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
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
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
OWNER SPECIAL:
Book Now for our July Special!
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
LAST MINUTE ALERT 8/16 - 8/23
OWNER SPECIAL:
Price reduction for water front cottage on Martha’s Vineyard. Was $3,500 now $2,800!!
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
OWNER SPECIAL:
UPDATE! July 26-Aug 2 now available!! Book now for 20% off Summer rates!!
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