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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.

237 Vacation Properties in Oak Bluffs
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
5 reviews read reviews
Summer:
$20,000 - $25,000/wk
Off Season:
$2,145 - $3,000/night
$10,000 - $25,000/wk
$35,000 - $60,000/mo

Oak Bluffs vacation rentals that sleep 18

Oak Bluffs
ID 38152
Summer:
$10,000 - $38,000/wk
Off Season:
$1,200 - $1,500/night
$9,000 - $26,000/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 - with AC units
Historic East Chop Beach House - with AC units
Distance to beach: 300 ft to Jetty Beach
5 reviews read reviews
Summer:
$10,000 - $13,500/wk
Off Season:
$9,000 - $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
OWNER SPECIAL:
JULY 14-21 JUST REDUCED!!!
Summer:
$11,700 - $19,500/wk
Off Season:
$1,000 - $2,000/night
$7,000 - $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 Town Beach
14 reviews read reviews
Summer:
$12,000 - $15,000/wk
Off Season:
$10,000 - $12,000/wk
3
Oak Bluffs
ID 19801
6 BR
4 ½ baths
Sleeps 16
Modern Renovated 6 bedroom Beautiful Pool, hot tub and pond
Modern Renovated 6 bedroom Beautiful Pool, hot tub and pond
Distance to beach: 1.5 miles State Beach and 15 Minutes to State Beach
4 reviews read reviews
Summer:
$14,500 - $16,500/wk
Off Season:
$1,500 - $2,000/night
$12,000 - $16,500/wk
4

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
12 reviews read reviews
Summer:
$7,990 - $8,600/wk
Off Season:
$600 - $800/night
$4,500 - $6,900/wk
4

Oak Bluffs vacation rentals that sleep 14

Oak Bluffs
ID 27190
7 BR
2 ½ baths
Sleeps 14
Beautiful Victorian: ''The Yellow House''
Beautiful Victorian: ''The Yellow House''
Distance to beach: Town/Inkwell Beach approx 100 yards
OWNER SPECIAL:
Great House! Weeks still open! 6/8 07/13, 08/24 & 08/31.
Summer:
$12,000 - $18,500/wk
Off Season:
$10,000 - $13,500/wk
Oak Bluffs
ID 35126
Summer:
$13,300 - $21,000/wk
Off Season:
$9,000 - $15,000/wk
Oak Bluffs
ID 26970
5 BR
2 ½ baths
Sleeps 14
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
3 reviews read reviews
Summer:
$7,500 - $12,000/wk
Off Season:
$5,000 - $6,500/wk
2
Oak Bluffs
ID 39105
5 BR
4 ½ baths
Sleeps 14
The Driftwood House Exquisite Waterfront Sanctuary
The Driftwood House Exquisite Waterfront Sanctuary
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
Summer:
$10,000 - $20,000/wk
Off Season:
$500 - $2,800/night
$5,000 - $15,000/wk
1

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
7 reviews read reviews
Summer:
$6,500 - $12,000/wk
Off Season:
$500 - $650/night
$3,000 - $6,500/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
11 reviews read reviews
Summer:
$8,000 - $10,000/wk
Off Season:
$7,500 - $9,000/wk
6
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
28 reviews read reviews
Summer:
$6,500/wk
Off Season:
$850 - $1,000/night
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!
11 reviews read reviews
OWNER SPECIAL:
CANCELLATION SPECIAL!! $1500 MULTI-WEEK DISCOUNT 2 FREE DAYS - FLEXIBLE ARRIVAL & DEPARTURE.
Summer:
$6,499 - $7,999/wk
Off Season:
$6,499/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
9 reviews read reviews
OWNER SPECIAL:
Just dropped prices AGAIN! Ferry reservations available 7/21-28 & 8/18-25.
Summer:
$7,000 - $14,000/wk
Off Season:
$600 - $900/night
$6,000 - $7,000/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
2 reviews read reviews
Summer:
$5,500 - $8,500/wk
Off Season:
$800/night
$3,000 - $5,700/wk
East Chop
ID 23424
6 BR
4 ½ baths
Sleeps 12
Large Renovated Home! Walk to Town and Beach! BOOKING 2024!
Large Renovated Home! Walk to Town and Beach! BOOKING 2024!
Distance to beach: 3/10 of a mile, 5 minute walk The Jetty Beach
3 reviews read reviews
Summer:
$9,000 - $12,000/wk
Off Season:
$750 - $1,500/night
$2,000 - $7,000/wk
4
Oak Bluffs
ID 29321
6 BR
4 baths
Sleeps 12
Oak Bluffs Victorian Home Across from Town Beach
Oak Bluffs Victorian Home Across from Town Beach
Distance to beach: 100 feet State Beach and Across the street from Town Beach
2 reviews read reviews
Summer:
$14,000 - $16,000/wk
3
East Chop
ID 20680
6 BR
2 baths
Sleeps 12
East Chop Marthas Vineyard Waterfront Ocean View Rental
East Chop Marthas Vineyard Waterfront Ocean View Rental
Distance to beach: 2/10 mile to Jetty Beach
2 reviews read reviews
OWNER SPECIAL:
July 15 - 22 Still Available! Ask About Our Discounted Rate!
Summer:
$6,000 - $8,000/wk
Off Season:
$5,000 - $7,000/wk
Oak Bluffs
ID 33717
Summer:
$12,900 - $20,900/wk
Off Season:
$1,475 - $1,595/night
$9,900 - $12,900/wk
2
Oak Bluffs
ID 34066
6 BR
3 baths
Sleeps 12
Beautiful Victorian 6 BR home in the heart of Oak Bluffs
Beautiful Victorian 6 BR home in the heart of Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
REDUCED RATES, BOOK NOW JUNETEENth (JUNE 16TH) JULY 7th,14th,21st& AUGUST 18th, 25th!
Summer:
$14,900 - $20,900/wk
Off Season:
$9,900 - $13,900/wk
Oak Bluffs
ID 38331
6 BR
3 ½ baths
Sleeps 12
Charming Victorian 6 BR Home in Oak Bluffs
Charming Victorian 6 BR Home in Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
GREAT WEEKS OPEN, BOOK NOW BEFORE THEY ARE GONE! JUNE 8th,22nd,29th; JULY 6th.
Summer:
$8,500 - $11,500/wk
Off Season:
$8,500 - $11,500/wk
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
Off Season:
$1,715 - $2,428/night
$9,100 - $13,500/wk
5
East Chop
ID 37848
6 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
1 review read review
Summer:
$12,500 - $20,000/wk
Off Season:
$10,000 - $12,500/wk
3
Oak Bluffs
ID 31220
Summer:
$6,000 - $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
1 review read review
Summer:
$8,000 - $9,500/wk
Off Season:
$6,000 - $8,500/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
9 reviews read reviews
Summer:
$6,000 - $8,000/wk
Off Season:
$4,500 - $5,500/wk
Oak Bluffs
ID 39247
5 BR
6 ½ baths
Sleeps 12
Grand Coastal-Style Estate In The Preserve With Pool/Hot Tub
Grand Coastal-Style Estate In The Preserve With Pool/Hot Tub
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
LAST MINUTE ALERT 6/9 - 6/16, 6/16 - 6/23 and 7/7 - 7/14
OWNER SPECIAL:
Ferry Tickets 7/14 - 7/21.
Summer:
$22,000 - $30,000/wk
Off Season:
$10,000 - $20,000/wk
Oak Bluffs
ID 11575
Summer:
$3,500 - $4,200/wk
Off Season:
$2,000 - $3,500/night
$3,010 - $4,200/wk
3
Oak Bluffs
ID 28460
5 BR
4 ½ baths
Sleeps 12
Pirate's Reef - NEW 5-bed, 4.5-bath w/full basement!
Pirate's Reef - NEW 5-bed, 4.5-bath w/full basement!
Distance to beach: 0.5 mile The Jetty Beach and 0.9 mile Oak Bluffs Town Beach
Summer:
$7,000 - $17,500/wk
Off Season:
$1,000 - $1,200/night
$5,000 - $8,000/wk
6
Lagoon Pond Waterfront-saltwat
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, 4kayaks,4-SUPs, beach chairs & toys
29 reviews read reviews
OWNER SPECIAL:
Aug wks w/ free car-ferry reservation (& Dscnt if 6 or < guests). Sept & Oct 3-nights just $5k.
Summer:
$2,500 - $3,000/night
$10,000 - $20,000/wk
Off Season:
$2,000 - $2,500/night
$6,500 - $14,000/wk
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
Summer:
$9,000 - $16,000/wk
Off Season:
$850 - $925/night
$5,000 - $9,000/wk
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:
$875 - $1,600/night
$5,000/wk
2

Oak Bluffs vacation rentals that sleep 11

Oak Bluffs
ID 15658
6 BR
2 ½ baths
Sleeps 11
4 Houses From the Beach, 1 1/2 Blocks from Circuit Ave.
4 Houses From the Beach, 1 1/2 Blocks from Circuit Ave.
Distance to beach: 75yds to Oak Bluffs Beach;150yds to Inkwell Beach
1 review read review
Summer:
$5,000 - $7,500/wk
Off Season:
$4,000 - $6,500/wk
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
3 reviews read reviews
Summer:
$4,500 - $7,500/wk
Off Season:
$3,750 - $4,000/wk
Oak Bluffs
ID 35433
5 BR
4 baths
Sleeps 11
Quiet, Newly Renovated Family Home, AC, Large Patio & Yard
Quiet, Newly Renovated Family Home, AC, Large Patio & Yard
Distance to beach: 2.9 mi to Oak Bluffs Town Beach and 4.0 mi to State Beach
3 reviews read reviews
Summer:
$6,600 - $8,500/wk
Off Season:
$700 - $800/night
$3,900 - $8,100/wk
2
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
6 reviews read reviews
Summer:
$6,000 - $8,000/wk
Off Season:
$3,000 - $5,000/wk
5
Oak Bluffs
ID 38007
4 BR
4 ½ baths
Sleeps 11
Luxury Waterfront w/ Dock, A/C All Bedrooms Ensuite w/Baths
Luxury Waterfront w/ Dock, A/C All Bedrooms Ensuite w/Baths
Distance to beach: 5 Minute Walk or Paddle to Sandy Beach
LAST MINUTE ALERT 7/6 - 7/13
OWNER SPECIAL:
Last minute 2 week cancellation! 7/6-7/20 Your gain. Price reduced by 2,000 per week. Gorgeous Spot!
Summer:
$9,500 - $16,500/wk
Off Season:
$7,500 - $12,500/wk
3

Oak Bluffs vacation rentals that sleep 10

OBT2089
ID 33751
7 BR
5 baths
Sleeps 10
Perfect Oak Bluffs Town Location
Perfect Oak Bluffs Town Location
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
Summer:
$14,900 - $20,900/wk
Off Season:
$9,900 - $13,900/wk
3
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
3 reviews read reviews
OWNER SPECIAL:
$1000 discount 6/24-7/1. Auto Ferry tickets to and from available for this and most open weeks.
Summer:
$5,000 - $7,000/wk
Off Season:
$2,000/night
$4,000/wk
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)
7 reviews read reviews
Summer:
$5,000 - $9,750/wk
Off Season:
$900 - $1,500/night
$3,000 - $4,800/wk
3
The Radcliffe House
ID 37237
6 BR
2 baths
Sleeps 10
Beautiful newly renovated 5bd/ 3 block from beach
Beautiful newly renovated 5bd/ 3 block from beach
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
4 reviews read reviews
Summer:
$7,000 - $10,000/wk
Off Season:
$645 - $1,000/night
$4,500 - $7,500/wk
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.
12 reviews read reviews
Summer:
$7,500 - $9,000/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
6 reviews read reviews
Summer:
$4,500 - $6,000/wk
Off Season:
$1,500 - $6,000/wk
$2,500 - $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
6 reviews read reviews
Summer:
$4,200 - $4,600/wk
Off Season:
$1,500 - $4,600/wk
2
Oak Bluffs
ID 19414
Summer:
$7,700 - $12,000/wk
Off Season:
$1,000 - $1,300/night
$7,000 - $8,400/wk
3
Oak Bluffs
ID 28697
5 BR
2 ½ baths
Sleeps 10
Great Location. Central AC. Easy walk to town & beach!
Great Location. Central AC. Easy walk to town & beach!
Distance to beach: Town / Inkwell Beach yards away
1 review read review
OWNER SPECIAL:
BOOK NOW! June 8th, 15th JUNETEENTH, and June 22nd OPEN!
Summer:
$9,000 - $15,500/wk
Off Season:
$8,000 - $9,000/wk
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
13 reviews read reviews
Summer:
$7,500 - $9,000/wk
Off Season:
$4,500 - $7,500/wk
4
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
7 reviews read reviews
Summer:
$4,150 - $6,250/wk
Off Season:
$4,150/wk
3
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
3 reviews read reviews
LAST MINUTE ALERT 6/30 - 7/7
OWNER SPECIAL:
Holiday Week!! $500 off!! June 30th- July 7th (July 4th week).
Summer:
$5,500 - $8,800/wk
Off Season:
$4,000 - $5,500/wk
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
3 reviews read reviews
Summer:
$7,000 - $11,000/wk
Off Season:
$5,000 - $7,750/wk
4
East Chop
ID 34693
Summer:
$7,900 - $8,900/wk
Off Season:
$1,000 - $1,200/night
$6,000 - $6,900/wk
5
Oak Bluffs
ID 34661
5 BR
5 ½ baths
Sleeps 10
Luxury 5 BR Home w/ heated saltwater pool at the Preserves
Luxury 5 BR Home w/ heated saltwater pool at the Preserves
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
July weeks still available Reduced rates BOOK NOW !
Summer:
$23,000 - $28,000/wk
Off Season:
$23,000 - $28,000/wk
Preserves
ID 33665
5 BR
5 ½ baths
Sleeps 10
New five bedroom home w/AC at the Preserve Woodlands
New five bedroom home w/AC at the Preserve Woodlands
Distance to beach: 3.4 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
BOOK NOW! All of JUNE OPEN Juneteenth (June 19th),JULY 4th &14TH, AUGUST 18TH and 25th!
Summer:
$14,500 - $18,500/wk
Off Season:
$12,000 - $14,500/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
1 review read review
Summer:
$9,000 - $17,000/wk
Off Season:
$6,000 - $9,000/wk
Oak Bluffs
ID 34873
5 BR
2 baths
Sleeps 10
5 BR Victorian Home in great location in Oak Bluffs
5 BR Victorian Home in great location in Oak Bluffs
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Week of July 7, 2024 is still available Book Now !
Summer:
$8,500 - $12,750/wk
Off Season:
$8,500 - $10,500/wk
Oak Bluffs
ID 36567
5 BR
3 ½ baths
Sleeps 10
The Ranch: Mid Century Style with Sunset View & AC
The Ranch: Mid Century Style with Sunset View & AC
Distance to beach: 0.8 miles Eastville Beach and 5 minute walk to beach at the end of Eastville Ave
1 review read review
Summer:
$7,875/wk
Off Season:
$7,875/wk
5
Near Farm Neck Golf Course
ID 38460
Summer:
$7,000 - $12,000/wk
Off Season:
$5,000 - $8,000/wk
2
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 read reviews
OWNER SPECIAL:
Stylish In-town O.B. Gingerbread.
Summer:
$10,000 - $16,000/wk
Off Season:
$900 - $1,200/night
$5,000 - $10,000/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
6 reviews read reviews
Summer:
$6,200 - $7,900/wk
Off Season:
$3,500 - $5,200/wk
Oak Bluffs
ID 26885
Summer:
$6,500 - $10,000/wk
Off Season:
$6,500 - $8,500/wk
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
24 reviews read reviews
Summer:
$3,850 - $5,000/wk
Off Season:
$3,350/wk
3
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:
$13,000 - $21,000/wk
$25,000 - $40,000/mo
Off Season:
$1,100 - $1,900/night
$7,700 - $13,000/wk
$15,000 - $42,000/mo
2
In-Town Oak Bluffs
ID 38018
Summer:
$5,600 - $9,500/wk
Off Season:
$875/night
$5,600 - $7,500/wk
2
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:
$10,500 - $16,000/wk
Off Season:
$1,250 - $1,500/night
$10,500 - $12,500/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
6 reviews read reviews
OWNER SPECIAL:
NO CLEANING FEE for MEMORIAL DAY or JULY 4TH RENTALS!!!
Summer:
$600 - $1,200/night
$7,500 - $8,000/wk
Off Season:
$500 - $1,000/night
$4,000 - $7,000/wk
3
Oak Bluffs
ID 32791
Summer:
$6,000 - $7,700/wk
Off Season:
$5,000 - $6,900/wk
3
Meadow View Farms
ID 33786
4 BR
2 ½ baths
Sleeps 10
Peaceful Meadows
Peaceful Meadows
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
8 reviews read reviews
Summer:
$4,800 - $6,000/wk
Off Season:
$480 - $600/night
$3,000 - $4,800/wk
4
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: House is on Lagoon Pond; 137 feet of private, sand
Summer:
$13,000 - $21,000/wk
Off Season:
$8,400 - $15,000/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
6 reviews read reviews
Summer:
$10,000 - $20,000/wk
Off Season:
$6,000 - $9,000/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:
$3,900 - $7,140/wk
Off Season:
$3,000 - $5,500/wk
Oak Bluffs
ID 37186
4 BR
3 ½ baths
Sleeps 10
Ocean View Oak Bluffs 2023 Renovation
Ocean View Oak Bluffs 2023 Renovation
Distance to beach: 3.6 mi to Oak Bluffs Town Beach and 5 min walk to Sengekontacket Pond
3 reviews read reviews
Summer:
$7,000 - $12,000/wk
Off Season:
$400 - $900/night
$4,000 - $8,000/wk
5
Oak Bluffs
ID 37145
Summer:
$6,000 - $13,500/wk
$30,000 - $40,000/mo
Off Season:
$450 - $750/night
$3,500 - $7,000/wk
$8,000 - $30,000/mo
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
2 reviews read reviews
Summer:
$775 - $1,800/night
$7,500 - $12,500/wk
Off Season:
$350 - $1,500/night
$3,500 - $7,500/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
LAST MINUTE ALERT 6/30 - 7/7
OWNER SPECIAL:
Dramatic Price Reduction (6/30 - 7/7/), Keep $1,505.00 in your pocket!
Summer:
$5,995 - $10,000/wk
Off Season:
$785 - $1,140/night
$4,000 - $8,000/wk
2
Oak Bluffs
ID 38969
4 BR
4 ½ baths
Sleeps 10
Main House Convenient Oak Bluffs Location 8019
Main House Convenient Oak Bluffs Location 8019
Distance to beach: 7/10 of a mile Oak Bluffs Town Beach
Summer:
$13,000 - $15,000/wk
Off Season:
$7,000 - $9,000/wk
Oak Bluffs
ID 38997
4 BR
2 baths
Sleeps 10
** 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
OWNER SPECIAL:
owner will be responsible for the lodging taxes.
Summer:
$5,300 - $8,500/wk
$20,000/mo
Off Season:
$500 - $830/night
$4,000 - $5,300/wk
$19,000/mo
4
Oak Bluffs
ID 33937
Summer:
$5,500 - $8,500/wk
Off Season:
$750 - $850/night
$2,500 - $7,000/wk

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:
$4,000 - $6,000/wk
Off Season:
$4,500 - $5,800/wk
Oak Bluffs The Preserves
ID 38276
5 BR
5 ½ baths
Sleeps 9
Experience the Vineyard at its Finest w/ Heated Pool
Experience the Vineyard at its Finest w/ Heated Pool
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
Summer:
$18,000 - $25,000/wk
Off Season:
$18,000 - $25,000/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:
$6,000 - $8,500/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
21 reviews read reviews
Summer:
$10,000 - $16,000/wk
Off Season:
$785 - $1,150/night
$6,500 - $8,000/wk
7
Oak Bluffs
ID 31591
4 BR
2 ½ baths
Sleeps 9
Oceanfront Home - Walk to Beach, Town & Ferry!
Oceanfront Home - Walk to Beach, Town & Ferry!
Distance to beach: 1/10 Oak Bluffs Town Beach and Oak Bluffs Town Beach (ocean) across the street
8 reviews read reviews
OWNER SPECIAL:
Just REDUCED rates! Car ferry for July 20 & 27 weeks!
Summer:
$9,500 - $15,900/wk
$45,000 - $60,000/mo
Off Season:
$7,500 - $11,500/wk
$15,000 - $38,000/mo
5
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 - $12,000/wk
Off Season:
$800/night
$5,600 - $7,000/wk
Oak Bluffs
ID 33354
Summer:
$8,500 - $11,500/wk
Off Season:
$3,500 - $9,000/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
3 reviews read reviews
Summer:
$5,000/wk
Off Season:
$3,000 - $5,000/wk
Oak Bluffs
ID 36607
4 BR
1 bath
Sleeps 9
5 min walk to lagoon w/new outdoor shower
5 min walk to lagoon w/new outdoor shower
Distance to beach: 1/4 mi to Lagoon in Oak Bluffs
4 reviews read reviews
Summer:
$2,850 - $4,500/wk
$18,000/mo
Off Season:
$400/night
$800 - $3,500/wk
Waterfront Home in Harthaven
ID 36784
Summer:
$14,000 - $15,500/wk
Off Season:
$1,750 - $2,000/night
$12,000 - $15,000/wk
Oak Bluffs
ID 38080
4 BR
4 baths
Sleeps 9
East Chop, Newly Renovated 4BR w/AC Walk to Beach & Downtown
East Chop, Newly Renovated 4BR w/AC Walk to Beach & Downtown
Distance to beach: 1.1 mi to The Jetty Beach and 1/2 mi to Marinelli Beach East Chop
4 reviews read reviews
OWNER SPECIAL:
Lots of availability 6/26-7/21. Willing to rent for less than a week if it works better for you.
Summer:
$7,000 - $11,500/wk
Off Season:
$800 - $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
1 review read review
Summer:
$4,550 - $10,000/wk
Off Season:
$430 - $1,000/night
$4,000 - $6,000/wk
3
Oak Bluffs
ID 35107
3 BR
3 ½ baths
Sleeps 9
Stately Home, Heated Pool, Breathtaking Waterview
Stately Home, Heated Pool, Breathtaking Waterview
Distance to beach: 1 mi to Jetty (Marinelli) Beach, 0.3 mi to Eastvi
OWNER SPECIAL:
Gorgeous Waterview's & pool June 15th,22nd; July 27th August 17th, 24th, 31st! HURRY!
Summer:
$17,000/wk
Off Season:
$17,000/wk

Oak Bluffs vacation rentals that sleep 8

Oak Bluffs
ID 21269
5 BR
1 ½ bath
Sleeps 8
Timeless Victorian w/Picturesque Waterviews, Walk to Town
Timeless Victorian w/Picturesque Waterviews, Walk to Town
Distance to beach: 100 Feet Oak Bluffs Town Beach and 100 feet to Inkwell Beach
OWNER SPECIAL:
"Juneteenth" (6/16/24) AND July is wide open , BOOK NOW!
Summer:
$6,000 - $7,000/wk
Off Season:
$6,000 - $6,500/wk
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
2 reviews read reviews
Summer:
$4,800 - $6,500/wk
Off Season:
$400 - $650/night
$3,000 - $5,500/wk
6
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
6 reviews read reviews
Summer:
$4,200 - $4,300/wk
Off Season:
$2,000 - $2,500/night
$2,000 - $4,200/wk
Oak Bluffs
ID 19225
4 BR
2 baths
Sleeps 8
OAK BLUFFS GETAWAY!
OAK BLUFFS GETAWAY!
Distance to beach: 1.1 mile to Inkwell Beach
15 reviews read reviews
Summer:
$5,000 - $8,000/wk
Off Season:
$4,000 - $5,000/wk
Oak Bluffs
ID 19626
Summer:
$2,800 - $4,000/wk
Off Season:
$250 - $775/night
$2,500 - $3,200/wk
4
Oak Bluffs
ID 25225
4 BR
1 ½ bath
Sleeps 8
Charmingly renovated house across from the Beach
Charmingly renovated house across from the Beach
Distance to beach: 2/10 mile to Oak Bluffs Town Beach and 200 feet to Inkwell Beach
19 reviews read reviews
Summer:
$6,000 - $10,000/wk
$32,000 - $40,000/mo
Off Season:
$6,000/wk
$24,000/mo
Oak Bluffs
ID 12643
Summer:
$3,500 - $6,800/wk
Off Season:
$490 - $690/night
$2,800 - $5,400/wk
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
6 reviews read reviews
Summer:
$4,600 - $6,300/wk
$26,000 - $28,800/mo
Off Season:
$3,000 - $5,300/wk
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
7 reviews read reviews
Summer:
$4,800 - $5,800/wk
Off Season:
$4,800/wk
4
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
4 reviews read reviews
Summer:
$3,850 - $4,550/wk
Off Season:
$500/night
$3,500 - $4,200/wk
4
Oak Bluffs
ID 29717
Summer:
$4,000 - $5,000/wk
Off Season:
$600 - $750/night
$4,000/wk
Oak Bluffs - Meadow View Farms
ID 29775
4 BR
4 ½ baths
Sleeps 8
Flexible turnover days for remaining July 2024 weeks!
Flexible turnover days for remaining July 2024 weeks!
Distance to beach: State Beach - 2 miles
30 reviews read reviews
OWNER SPECIAL:
Flexible turnover days and $500 off per week on remaining 2024 summer weeks!
Summer:
$5,500 - $6,800/wk
Off Season:
$3,500 - $6,000/wk
5
Oak Bluffs
ID 28871
4 BR
2 baths
Sleeps 8
7/27-8/3 w Ferry tickets A/C O/D Shower, Fenced Yard, Dogs
7/27-8/3 w Ferry tickets A/C O/D Shower, Fenced Yard, Dogs
Distance to beach: Under 1/2 mile to Inkwell, Jetty and Pay Beach
5 reviews read reviews
OWNER SPECIAL:
July 27-August 3rd .Offering Complimentary Ferry tickets! Walk to everything Oak Bluffs!
Summer:
$4,500 - $6,500/wk
Off Season:
$3,800 - $6,000/wk
$3,000 - $3,500/mo
6
Walk to town, and beach, shops
ID 29080
4 BR
2 baths
Sleeps 8
Walk to town and beach Oak Bluffs 4 bedrooms renovated home
Walk to town and beach Oak Bluffs 4 bedrooms renovated home
Distance to beach: Oak Bluffs State Beach and 1/2 mile to Oak Bluffs town beach, East Chop beach
3 reviews read reviews
Summer:
$1,000/night
$4,000 - $10,000/wk
Off Season:
$800 - $900/night
$3,000 - $4,500/wk
7
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
4 reviews read reviews
Summer:
$6,100 - $7,500/wk
Off Season:
$6,100 - $6,500/wk
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
8 reviews read reviews
Summer:
$4,100 - $5,200/wk
Off Season:
$400 - $660/night
$2,800 - $5,000/wk
4
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
14 reviews read reviews
Summer:
$800 - $1,200/night
$4,900 - $8,400/wk
Off Season:
$600 - $1,200/night
$3,500 - $6,650/wk
$6,500/mo
3
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
4 reviews read reviews
LAST MINUTE ALERT 7/7 - 7/14
OWNER SPECIAL:
JULY WEEKS AVAILABLE DUE TO CANCELLATION: The weeks of 7/7 and 7/14 are both available.
Summer:
$4,000 - $12,500/wk
Off Season:
$2,500 - $4,000/wk
$2,800 - $3,200/mo
5
Oak Bluffs
ID 32817
4 BR
3 ½ baths
Sleeps 8
Exquisite pool home! RT 7/27-8/3 & 8/31-9/7 FERRY TIX. A/C
Exquisite pool home! RT 7/27-8/3 & 8/31-9/7 FERRY TIX. A/C
Distance to beach: 1 and 2/10 mile Oak Bluffs Town Beach and 3 miles State Beach
7 reviews read reviews
Summer:
$7,500 - $16,500/wk
Off Season:
$4,000 - $9,000/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
13 reviews read reviews
Summer:
$3,500 - $4,620/wk
Off Season:
$450 - $500/night
$1,200 - $4,000/wk
3
Oak Bluffs
ID 32868
4 BR
2 ½ baths
Sleeps 8
Spacious 4 BR Home near Inkwell Beach, Private Tennis Court
Spacious 4 BR Home near Inkwell Beach, Private Tennis Court
Distance to beach: 5 minute walk to Oak BluffsTown & Inkwell Beaches
OWNER SPECIAL:
BOOK NOW! JUNETEENTH June 15th & July 13th OPEN!
Summer:
$8,500 - $9,500/wk
Off Season:
$7,500 - $9,500/wk
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
4 reviews read reviews
Summer:
$7,000 - $10,000/wk
Off Season:
$5,250 - $6,000/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
12 reviews read reviews
OWNER SPECIAL:
Last minute availability June 8-22. Best deal on the island!
Summer:
$4,000 - $8,000/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:
$4,900 - $10,000/wk
Off Season:
$4,400 - $5,700/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
Summer:
$17,500 - $25,000/wk
Off Season:
$13,000 - $17,500/wk
3
Oak Bluffs
ID 35168
4 BR
6 ½ baths
Sleeps 8
Luxury Contemporary Vacation Home W/ Heated Pool
Luxury Contemporary Vacation Home W/ Heated Pool
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
FILM FESTIVAL JUST OPENED UP 8/4/24 BOOK FAST, plus week of July 28, 2024.
Summer:
$27,000 - $34,000/wk
Off Season:
$17,000 - $29,500/wk
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
7 reviews read reviews
OWNER SPECIAL:
Rates reduced in July and August!
Summer:
$7,500 - $10,000/wk
Off Season:
$500 - $1,000/night
$3,500 - $7,800/wk
5
East Chop
ID 33664
4 BR
3 baths
Sleeps 8
Timeless East Chop Renovated 1920 Cottage w/AC
Timeless East Chop Renovated 1920 Cottage w/AC
Distance to beach: 8/10 mi to The Jetty Beach
Summer:
$7,500 - $10,500/wk
Off Season:
$7,000 - $8,750/wk
Oak Bluffs
ID 35279
Summer:
$6,000 - $8,000/wk
Off Season:
$6,000 - $6,500/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
2 reviews read reviews
Summer:
$4,800 - $6,800/wk
Off Season:
$4,800 - $5,800/wk
3
Oak Bluffs
ID 27205
4 BR
4 ½ baths
Sleeps 8
Contemporary Home with Heated Pool/Spa - Pay No Room Tax
Contemporary Home with Heated Pool/Spa - Pay No Room Tax
Distance to beach: Inkwell Beach is 1.5 miles away
Summer:
$12,000 - $18,000/wk
Oak Bluffs
ID 35858
4 BR
2 ½ baths
Sleeps 8
Brendas Cottage
Brendas Cottage
Distance to beach: 0.9 State Beach
7 reviews read reviews
Summer:
$4,000 - $6,000/wk
Off Season:
$3,500 - $5,000/wk
$5,000 - $8,000/mo
5
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 read reviews
LAST MINUTE ALERT 6/23 - 6/30, 6/30 - 7/7 and 7/7 - 7/14
OWNER SPECIAL:
Amazing Summer special! Save $1,000! Now only $6,000 for week.
Summer:
$4,000 - $10,500/wk
Off Season:
$4,900/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:
$6,000 - $7,000/wk
Off Season:
$6,000 - $6,500/wk
Oak Bluffs
ID 36835
4 BR
3 ½ baths
Sleeps 8
Newly Built Farmhouse in Oak Bluffs with Pool!
Newly Built Farmhouse in Oak Bluffs with Pool!
Distance to beach: 2.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Weeks of 8/18-8/25 are now $14,000, and 8/25-9/1 and 9/1-9/8 are now $12,000. BOOK NOW!
Summer:
$12,000 - $18,000/wk
Off Season:
$1,100 - $1,300/night
$8,000 - $12,000/wk
Oak Bluffs
ID 31476
4 BR
2 baths
Sleeps 8
Fun, Family, Vineyard Getaway
Fun, Family, Vineyard Getaway
Distance to beach: Lagoon 0.3 mi, State beach 1.5 mi
1 review read review
OWNER SPECIAL:
Flexible dates! Prices reduced.
Summer:
$3,000 - $12,000/wk
Off Season:
$370 - $500/night
$2,000 - $4,500/wk
4
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:
Rate posted is now $900 OFF of July/June dates.FERRY Tickets may be available if you contact owner.
Summer:
$4,100 - $7,400/wk
Off Season:
$3,000 - $6,000/wk
Oak Bluffs
ID 37238
Summer:
$4,000 - $5,500/wk
Off Season:
$2,500 - $4,000/wk
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
OWNER SPECIAL:
BOOK NOW! June 1st, 8th, 15th OPEN JULY 6TH & 27th are still available. Great weeks!
Summer:
$5,500 - $6,000/wk
Off Season:
$5,500 - $6,000/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
OWNER SPECIAL:
JULY AND AUGUST WEEKS REDUCED!!!
Summer:
$7,000 - $9,000/wk
Off Season:
$500 - $1,200/night
$7,000/wk
Oak Bluffs
ID 37484
4 BR
2 baths
Sleeps 8
Nashawena Park Home- Close to Inkwell and town
Nashawena Park Home- Close to Inkwell and town
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
Summer:
$6,000 - $7,500/wk
Off Season:
$1,000 - $1,500/night
$6,000 - $7,000/wk
3
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
Summer:
$5,300 - $6,750/wk
Off Season:
$430 - $860/night
$3,000 - $6,000/wk
5
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
OWNER SPECIAL:
Renovated Kitchen and First Floor Bathroom.
Summer:
$4,200 - $6,500/wk
Off Season:
$4,200 - $5,200/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
Summer:
$4,000 - $6,000/wk
$15,000 - $18,000/mo
Off Season:
$2,500 - $4,500/wk
$5,000 - $8,000/mo
3
Oak Bluffs
ID 38862
Summer:
$3,200 - $5,700/wk
Off Season:
$3,000 - $3,200/wk
1
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
LAST MINUTE ALERT 6/30 - 7/7 and 7/7 - 7/14
OWNER SPECIAL:
Just Reduced weeks of 6/30 and 7/7 Oak Bluffs 4 bedroom Home.
Summer:
$4,200 - $6,900/wk
Off Season:
$500 - $850/night
$3,200 - $5,900/wk
2
Oak Bluffs
ID 38972
4 BR
3 baths
Sleeps 8
4 BR 3 Bath Colonial Home
4 BR 3 Bath Colonial Home
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Great weeks available! June 30th, July 7th,14th,21st, 28th & August 18,2024.
Summer:
$8,750 - $12,500/wk
Off Season:
$8,750/wk
Oak Bluffs
ID 38738
4 BR
2 ½ baths
Sleeps 8
Harper House - Waterfront Luxury Rental
Harper House - Waterfront Luxury Rental
Distance to beach: 1/2 mi to Eastville Beach
Summer:
$3,200 - $4,000/night
$17,000 - $30,000/wk
$106,000 - $130,000/mo
Off Season:
$2,200 - $2,500/night
$14,000 - $18,000/wk
$72,000 - $120,000/mo
Oak Bluffs
ID 39256
4 BR
4 ½ baths
Sleeps 8
Luxurious Oak Bluffs Contemporary With Water Views
Luxurious Oak Bluffs Contemporary With Water Views
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
Summer:
$8,500 - $13,000/wk
Off Season:
$785 - $1,000/night
$5,500 - $10,000/wk
Oak Bluffs
ID 25368
4 BR
3 baths
Sleeps 8
Spacious retreat, just steps to Lagoon Beach
Spacious retreat, just steps to Lagoon Beach
Distance to beach: Lagoon Beach, approx. 500 feet
2 reviews read reviews
Summer:
$3,500 - $4,450/wk
Off Season:
$450 - $636/night
$3,000 - $4,000/wk
3
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:
$7,000 - $8,000/wk
Off Season:
$1,000 - $1,200/night
$6,200 - $7,500/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:
$5,000 - $6,000/wk
Off Season:
$375 - $450/night
$5,000/wk
2
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:
$6,265 - $11,900/wk
Off Season:
$3,150 - $7,200/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: Equidistant to OB, State, VH & Edgartown Beaches
3 reviews read reviews
Summer:
$5,500 - $9,500/wk
Off Season:
$500 - $800/night
$4,000 - $6,500/wk
Oak Bluffs
ID 35161
Summer:
$4,500 - $5,000/wk
Off Season:
$750/night
$3,500 - $5,000/wk
2
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
OWNER SPECIAL:
NO CAR NEEDED !! WALK TO OAK BLUFFS FERRIES~ PRICES JUST SLASHED!
Summer:
$7,000 - $11,000/wk
Off Season:
$750 - $2,000/night
$10,000/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
Summer:
$5,500 - $8,000/wk
Off Season:
$600 - $800/night
$7,500 - $8,000/wk
Oak Bluffs
ID 35791
3 BR
2 ½ baths
Sleeps 8
3 BR Cottage in Oak Bluffs Minutes Away from Town & Beach
3 BR Cottage in Oak Bluffs Minutes Away from Town & Beach
Distance to beach: 0.4 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
LAST CHANCE TO BOOK FIRST THREE WEEKS IN JUNE INCLUDING JUNETEENTH, WONT LAST LONG !
Summer:
$6,800 - $8,800/wk
Off Season:
$6,800/wk
East Chop
ID 37607
Summer:
$4,500 - $7,500/wk
Off Season:
$750 - $850/night
$3,500 - $5,500/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
4 reviews read reviews
OWNER SPECIAL:
PRICES REDUCED!! 1.4 MILES TO INKWELL BEACH.!
Summer:
$4,000 - $7,500/wk
Off Season:
$500 - $1,000/night
$4,000 - $5,500/wk
Town
ID 38903
3 BR
2 baths
Sleeps 8
The Jessie Lee Harris Legacy House
The Jessie Lee Harris Legacy House
Distance to beach: 1.1 mi to Oak Bluffs Town Beach
Summer:
$4,000 - $10,000/wk
Off Season:
$3,000 - $6,000/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
2 reviews read reviews
Summer:
$2,100 - $4,200/wk
Off Season:
$2,100 - $4,200/wk
East Chop
ID 35529
Summer:
$3,900 - $5,000/wk
$15,000/mo
Off Season:
$3,500 - $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:
$3,200/wk
Off Season:
$400 - $600/night
$3,200/wk
Oak Bluffs
ID 37704
4 BR
2 ½ baths
Sleeps 7
East Chop A Frame/Walk to Beach
East Chop A Frame/Walk to Beach
Distance to beach: 1/2 mi to Tisbury Town Beach
Summer:
$6,500 - $8,000/wk
$27,000 - $30,000/mo
Off Season:
$6,500/wk
3
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
8 reviews read reviews
Summer:
$3,200/wk
Off Season:
$2,600 - $3,200/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
14 reviews read reviews
Summer:
$3,500 - $4,000/wk
Off Season:
$2,900 - $3,400/wk
6
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
3 reviews read reviews
Summer:
$3,000 - $3,900/wk
$12,000/mo
Off Season:
$350 - $500/night
$2,500 - $3,000/wk
$8,000 - $11,000/mo
4
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
2 reviews read reviews
OWNER SPECIAL:
Hurry! Week of 8/25 is still open! Book before June 1 for special discount off listed rate!
Summer:
$5,500 - $9,000/wk
Off Season:
$2,500 - $5,000/wk
Oak Bluffs
ID 32945
3 BR
2 baths
Sleeps 7
Walk to Private Gull Landing Lagoon Beach
Walk to Private Gull Landing Lagoon Beach
Distance to beach: Short walk to deeded beach
1 review read review
Summer:
$3,700 - $4,500/wk
Off Season:
$350 - $500/night
$3,500 - $3,800/wk
Oak Bluffs
ID 33550
3 BR
3 baths
Sleeps 7
MV Memories made at this charming and pristine home!
MV Memories made at this charming and pristine home!
Distance to beach: 2 miles Oak Bluffs Town Beach and 1.5 Eastville Beach
21 reviews read reviews
OWNER SPECIAL:
FREE car ferry tickets until 6/13 for July 14-21! Book fast before they're GONE.
Summer:
$5,800 - $7,200/wk
Off Season:
$700 - $1,200/night
$5,300 - $5,900/wk
7
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
5 reviews read reviews
Summer:
$5,000 - $6,995/wk
Off Season:
$3,950 - $5,000/wk
4
Lagoon
ID 38690
3 BR
2 baths
Sleeps 7
Waterfront Home With Private Beach in Oak Bluffs
Waterfront Home With Private Beach in Oak Bluffs
Distance to beach: 2.4 mi Oak Bluffs Town Beach and 100 ft to Private beach downhill on a path
Summer:
$6,000 - $12,000/wk
Off Season:
$3,500 - $7,500/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
13 reviews read reviews
Summer:
$3,400 - $4,800/wk
Off Season:
$2,600 - $3,400/wk
3

Oak Bluffs vacation rentals that sleep 6

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
2 reviews read reviews
OWNER SPECIAL:
GRAND ILLUMINATION WEEK. 8/11-18,$8000.00.
Summer:
$2,400 - $9,500/wk
$36,500 - $39,000/mo
Off Season:
$2,800 - $9,500/wk
$20,000 - $30,400/mo
3
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)
3 reviews read reviews
Summer:
$800 - $1,000/night
$2,500 - $3,700/wk
$14,000 - $16,000/mo
Off Season:
$600 - $800/night
$1,500 - $2,800/wk
$2,000 - $12,000/mo
7
Oak Bluffs
ID 9028
3 BR
2 ½ baths
Sleeps 6
Vineyard Retreat - The perfect place to rest and relax
Vineyard Retreat - The perfect place to rest and relax
Distance to beach: 2/10 mile to a beach on a large 3,968 acre pond
16 reviews read reviews
Summer:
$3,500 - $4,200/wk
$13,000 - $16,000/mo
Off Season:
$3,000 - $3,500/wk
$10,000 - $15,000/mo
4
Oak Bluffs
ID 12452
3 BR
1 ½ bath
Sleeps 6
Simple, easy and comfortable Island home
Simple, easy and comfortable Island home
Distance to beach: 1/4 mile to Eastville Beach
6 reviews read reviews
OWNER SPECIAL:
Price reduced for last summer week avail 7/21-28.
Summer:
$400/night
$2,950 - $3,500/wk
Off Season:
$340/night
$2,000 - $2,750/wk
3
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
11 reviews read reviews
OWNER SPECIAL:
Fourth of July week Reduced to $3500, June 29-July 6!
Summer:
$4,000 - $4,800/wk
$10,000 - $14,000/mo
Off Season:
$4,300/wk
2
Oak Bluffs
ID 21790
3 BR
1 ½ bath
Sleeps 6
Ideal location, short walk to Town&Beach, FERRY RESERVATIONS
Ideal location, short walk to Town&Beach, FERRY RESERVATIONS
Distance to beach: 7 min walk Oak Bluffs Town Beach and 7-minute walk to Inkwell Beach
9 reviews read reviews
OWNER SPECIAL:
Wk 7/20-27 price special! Either Sat-Sat or Sun-Fri, prorated. Ferry reservations available.
Summer:
$2,595 - $4,495/wk
Off Season:
$2,495 - $3,295/wk
Oak Bluffs
ID 4217
Summer:
$5,500 - $7,000/wk
Off Season:
$450/night
$5,200/wk
3
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
13 reviews read 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
9 reviews read reviews
OWNER SPECIAL:
Transferable ferry tickets available for the week of 7/7- 7/14.
Summer:
$3,100 - $3,700/wk
6
Oak Bluffs
ID 20575
3 BR
3 baths
Sleeps 6
Bright Modern House w/ AC-Sleeps 8 Walk to Beach & Shops
Bright Modern House w/ AC-Sleeps 8 Walk to Beach & Shops
Distance to beach: Lagoon Beach-end of block;15 min bike- State Beach
2 reviews read reviews
Summer:
$500 - $750/night
$3,500 - $5,250/wk
$15,000 - $19,000/mo
Off Season:
$100 - $450/night
$3,000 - $4,900/wk
$11,000 - $15,000/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
27 reviews read reviews
Summer:
$5,425 - $7,400/wk
Off Season:
$800/night
$4,200 - $6,600/wk
6
Oak Bluffs
ID 10809
3 BR
2 ½ baths
Sleeps 6
Beautiful Getaway home in Oak Bluffs
Beautiful Getaway home in Oak Bluffs
Distance to beach: 1 mile Oak Bluffs Town Beach and 1.5 miles State Beach
8 reviews read reviews
Summer:
$3,000 - $8,500/wk
$14,000 - $30,500/mo
Off Season:
$1,000 - $3,500/wk
$3,000 - $11,400/mo
4
32 County Road, Oak Bluffs
ID 31344
Summer:
$6,900 - $8,450/wk
Off Season:
$6,900/wk
2
Oak Bluffs
ID 32157
Summer:
$3,800 - $5,000/wk
Off Season:
$2,500 - $3,800/wk
2
Oak Bluffs
ID 33125
Summer:
$2,800 - $3,300/wk
Off Season:
$2,600/wk
Near MV Hospital
ID 33461
3 BR
1 bath
Sleeps 6
3 Bedrooms on OB's Towanticut St. New living room furnIture.
3 Bedrooms on OB's Towanticut St. New living room furnIture.
Distance to beach: 7/10 mi to The Jetty Beach and 1/2 mi to Eastville Beach
OWNER SPECIAL:
Flexible Start Date - Daily Rate of $400 with Minimum 5-Day Stay-This offer Won't Last!
Summer:
$2,850 - $3,150/wk
Off Season:
$2,250 - $3,150/wk
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:
price reduced TO $2800 rent- LONG WEEK AVAIL: FRI July 5 to SAT July 13 AVAIL!
Summer:
$2,800 - $3,800/wk
Off Season:
$3,600/wk
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
10 reviews read reviews
Summer:
$3,650 - $6,000/wk
Off Season:
$600 - $800/night
$3,500 - $3,700/wk
3
Oak Bluffs
ID 34492
3 BR
2 ½ baths
Sleeps 6
Heated pool, stunning sunsets, 2 kayaks!
Heated pool, stunning sunsets, 2 kayaks!
Distance to beach: 3/10 mi to Lagoon Pond Public Beach Oak Bluffs Town Beach
11 reviews read reviews
OWNER SPECIAL:
PRICE REDUCED for last week in August! Transferable FERRY TICKETS AVAILABLE.
Summer:
$7,900 - $11,400/wk
Off Season:
$900 - $1,200/night
$6,500 - $6,900/wk
$17,000/mo
5
Oak Bluffs
ID 35304
3 BR
3 ½ baths
Sleeps 6
Beautiful Newly-Built 3 Bedroom Home w/AC in Oak Bluffs
Beautiful Newly-Built 3 Bedroom Home w/AC in Oak Bluffs
Distance to beach: 1.9 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
BOOK NOW! JULY is ALL OPEN! WON'T LAST LONG!
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
3 reviews read reviews
Summer:
$3,000 - $4,700/wk
Off Season:
$500/night
$3,000 - $3,200/wk
7
East Chop
ID 35125
3 BR
2 baths
Sleeps 6
Lovely Oak Bluffs Cottage Close to Town
Lovely Oak Bluffs Cottage Close to Town
Distance to beach: 0.5 mi to The Jetty Beach
15 reviews read reviews
OWNER SPECIAL:
*** Round-trip Auto Ferry Ticket Included for July 13-20! ***.
Summer:
$3,000 - $6,000/wk
Off Season:
$300 - $500/night
$2,800 - $4,800/wk
6
Oak Bluffs
ID 35638
3 BR
2 ½ baths
Sleeps 6
Modern Gingerbread Home, Walking Distance to Lagoon
Modern Gingerbread Home, Walking Distance to Lagoon
Distance to beach: 1.5 mi to Oak Bluffs Town Beach and 1.0 mi to Eastville Beach
Summer:
$4,900 - $6,650/wk
Off Season:
$700/night
5
Oak Bluffs
ID 21030
3 BR
2 ½ baths
Sleeps 6
OB Hide-Away, Tucked Away yet Close to Towns and Beaches
OB Hide-Away, Tucked Away yet Close to Towns and Beaches
Distance to beach: 3 miles State Beach and .75 mile Eastville Beach
3 reviews read reviews
Summer:
$4,900 - $5,900/wk
Off Season:
$4,500 - $5,300/wk
Oak Bluffs
ID 36742
3 BR
2 baths
Sleeps 6
Beautiful Inground Pool, Central Location
Beautiful Inground Pool, Central Location
Distance to beach: 4.4 miles Oak Bluffs Town Beach
1 review read review
Summer:
$2,500 - $6,500/wk
Off Season:
$300 - $350/night
$1,500 - $4,400/wk
Oak Bluffs
ID 36904
3 BR
2 baths
Sleeps 6
East Chop Tree Tops
East Chop Tree Tops
Distance to beach: 0.9 miles The Jetty Beach and 1.1 miles Eastville Beach
Summer:
$2,449 - $3,999/wk
Off Season:
$395 - $449/night
$2,449 - $2,999/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:
$595 - $725/night
$4,500 - $5,000/wk
Off Season:
$575 - $725/night
$3,500 - $5,000/wk
3
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
1 review read review
Summer:
$5,500 - $9,900/wk
Off Season:
$2,800 - $4,300/wk
Oak Bluffs
ID 37987
Summer:
$450 - $835/night
$2,500 - $6,000/wk
Off Season:
$400/night
$2,500 - $4,000/wk
Oak Bluffs
ID 35664
3 BR
3 baths
Sleeps 6
Perfect Family House W/ FERRY TICKETS - Walk to Lagoon
Perfect Family House W/ FERRY TICKETS - Walk to Lagoon
Distance to beach: 2 blks to Lagoon Pond;1mi to Oak Bluffs Town Beach
1 review read review
Summer:
$3,000 - $5,000/wk
Off Season:
$500 - $600/night
$1,800 - $3,000/wk
2
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 6/22 - 6/29 and 7/13 - 7/20
OWNER SPECIAL:
10% off last minute special!
Summer:
$3,325 - $7,980/wk
$25,000 - $30,000/mo
Off Season:
$550 - $675/night
$3,000 - $3,850/wk
$15,000 - $25,000/mo
Oak Bluffs
ID 38381
3 BR
1 ½ bath
Sleeps 6
History and Heritage Awaits/Walk to Beach
History and Heritage Awaits/Walk to Beach
Distance to beach: 0.5 mi to The Jetty Beach
LAST MINUTE ALERT 6/9 - 6/16
OWNER SPECIAL:
Last minute cancellation puts money in your pocket. Save $500 for the week.
Summer:
$3,500 - $4,000/wk
$12,000 - $15,000/mo
Off Season:
$2,000 - $3,000/wk
$3,500 - $8,000/mo
4
Oak Bluffs
ID 38584
Summer:
$4,000 - $5,500/wk
Off Season:
$4,000 - $5,500/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
4 reviews read reviews
Summer:
$3,150 - $4,500/wk
Off Season:
$400 - $500/night
$3,150 - $3,900/wk
Oak Bluffs
ID 38836
3 BR
1 ½ bath
Sleeps 6
Oak Bluffs Victorian Gingerbread Cottage
Oak Bluffs Victorian Gingerbread Cottage
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Reduced rates weeks still open JULY 21st, 28th, AUGUST 18th & 25th.
Summer:
$4,500 - $5,000/wk
Off Season:
$5,000/wk
East Chop
ID 34478
3 BR
2 baths
Sleeps 6
East Chop Oak Bluffs w/Central AC
East Chop Oak Bluffs w/Central AC
Distance to beach: 0.8 mi to The Jetty Beach
Summer:
$3,750 - $4,900/wk
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
15 reviews read reviews
Summer:
$5,250 - $7,875/wk
Off Season:
$3,990 - $4,900/wk
Oak Bluffs
ID 19888
Summer:
$2,000 - $3,450/wk
Off Season:
$1,800 - $2,600/wk
Oak Bluffs
ID 21831
3 BR
1 bath
Sleeps 6
Hillrest-Overlooking Sunset Lake in OB
Hillrest-Overlooking Sunset Lake in OB
Distance to beach: 2 miles Eastville Beach and Oak Bluffs Town Beach under 1/2 mile
Summer:
$200 - $2,900/wk
East Chop
ID 32946
Summer:
$3,500 - $5,000/wk
Off Season:
$2,500 - $4,000/wk
5
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
$14,000/mo
Off Season:
$1,000 - $3,000/wk
$4,500 - $12,000/mo
2
Oak Bluffs
ID 37349
Summer:
$550 - $4,900/wk
Off Season:
$3,850/wk
Oak Bluffs
ID 38229
3 BR
3 ½ baths
Sleeps 6
Newly-Renovated 3BR/3.5Bath House
Newly-Renovated 3BR/3.5Bath House
Distance to beach: 4.5 mi to State Beach (Joseph Sylvia State Beach) and 7 mi to South Beach - Katama
Summer:
$4,800 - $10,000/wk
Off Season:
$500 - $750/night
$3,000 - $6,000/wk
4
Oak Bluffs
ID 27087
2 BR
1 bath
Sleeps 6
Oak Bluffs Getaway
Oak Bluffs Getaway
Distance to beach: Lagoon
Summer:
$1,900 - $2,000/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
2 reviews read reviews
Summer:
$3,600 - $4,550/wk
Off Season:
$390 - $500/night
$3,325 - $3,600/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:
$4,200 - $6,000/wk
Off Season:
$500 - $1,000/night
$4,000 - $6,000/wk
3
Oak Bluffs
ID 38986
2 BR
2 ½ baths
Sleeps 6
Happy Place in OB
Happy Place in OB
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
Summer:
$4,900 - $7,000/wk
Off Season:
$700 - $800/night
$3,850 - $6,500/wk
5

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 reviews read reviews
Summer:
$3,595 - $4,695/wk
Off Season:
$3,495/wk
Oak Bluffs, near Inkwell Beach
ID 24640
3 BR
1 ½ bath
Sleeps 5
Jingle Shell Cottage, quiet locale, walk to beach & town!
Jingle Shell Cottage, quiet locale, walk to beach & town!
Distance to beach: 1200 feet Oak Bluffs Town Beach and 1000 feet to Inkwell Beach
2 reviews read reviews
Summer:
$3,495 - $4,495/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
1 review read review
Summer:
$2,700 - $3,000/wk
Off Season:
$275 - $325/night
$1,600 - $2,500/wk
2
Oak Bluffs
ID 34708
2 BR
1 bath
Sleeps 5
Sunny Cottage short walk to Lagoon Sunset!
Sunny Cottage short walk to Lagoon Sunset!
Distance to beach: 1.4 mi to Oak Bluffs Town Beach and 1.4 mi to Eastville Beach
4 reviews read reviews
Summer:
$3,000 - $4,500/wk
Off Season:
$3,000/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
2 reviews read reviews
Summer:
$3,500 - $6,500/wk
Off Season:
$500/night
$3,500 - $6,000/wk

Oak Bluffs vacation rentals that sleep 4

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
Summer:
$4,620 - $8,050/wk
Off Season:
$2,975 - $5,040/wk
Oak Bluffs on the Edgartown li
ID 37184
2 BR
1 ½ bath
Sleeps 4
Quiet and Comfortable - Come and Stay a While!
Quiet and Comfortable - Come and Stay a While!
Distance to beach: 5.5 miles State Beach and 7 miles South Beach - Katama
Summer:
$2,800 - $3,500/wk
$10,000/mo
Off Season:
$350 - $440/night
$2,800 - $3,000/wk
$10,000/mo
East Chop
ID 38085
2 BR
1 bath
Sleeps 4
Gorgeous Cabin with Gorgeous Views (Walk to beach and town)
Gorgeous Cabin with Gorgeous Views (Walk to beach and town)
Distance to beach: 0.5 mi to The Jetty Beach and 0.5 mi to Oak Bluffs Town Beach
1 review read review
OWNER SPECIAL:
Last Minute Cancellation + Price Reduction :).
Summer:
$6,000 - $7,000/wk
Off Season:
$5,500 - $7,000/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:
$500 - $600/night
$3,150 - $6,650/wk
$15,000 - $22,000/mo
Off Season:
$450 - $500/night
$3,150 - $3,850/wk
$12,000 - $20,000/mo
Oak Bluffs
ID 39209
2 BR
1 ½ bath
Sleeps 4
Quail Run Condo
Quail Run Condo
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
Summer:
$2,800 - $5,000/wk
Off Season:
$2,800 - $3,500/wk
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
6 reviews read reviews
Summer:
$3,000 - $5,000/wk
Off Season:
$3,000/wk
3
Oak Bluffs
ID 36682
1 BR
1 bath
Sleeps 4
Ocean-facing Guest House, Walk Everywhere!
Ocean-facing Guest House, Walk Everywhere!
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
2 reviews read reviews
OWNER SPECIAL:
Ask about flexible dates!
Summer:
$2,800 - $3,500/wk
$7,000 - $11,000/mo
Off Season:
$425 - $525/night
$1,900 - $3,000/wk
$5,000 - $10,000/mo
Oak Bluffs
ID 37211
1 BR
1 bath
Sleeps 4
Relax and Rejuvenate in a brand new cozy apartment!
Relax and Rejuvenate in a brand new cozy apartment!
Distance to beach: 2.8 mi to Oak Bluffs Town Beach and .4 mi to Sailing Camp Beach
Summer:
$250 - $500/night
$2,000 - $3,500/wk
$9,000 - $13,000/mo
Off Season:
$250 - $500/night
$2,000 - $3,000/wk
$2,500 - $11,000/mo
6
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
3 reviews read reviews
Summer:
$10,000/mo
Off Season:
$9,000 - $10,000/mo

Oak Bluffs vacation rentals that sleep 3

Oak Bluffs
ID 34370