Oak Bluffs
ID 38152
- 9 BR
- 6 baths
- Sleeps 18
Spectacular Views Completely Updated w/Guest Home- Sleeps 18
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Off Season:
$1,500 - $1,700/night
$1,700 - $20,500/wk
Oak Bluffs Vacation Rentals
241 properties
Oak Bluffs vacation rentals that sleep 18
Historic Copeland District
ID 35193
- 8 BR
- 3 baths
- Sleeps 18
8 BR Grand Victorian near Inkwell Beach sleeps 18 people!
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$16,500 - $25,500/wk
Off Season:
$1,500 - $2,000/night
$9,500 - $13,500/wk
Oak Bluffs
ID 41921
- 7 BR
- 4 baths
- Sleeps 18
Centrally Located, Iconic Oceanfront Home, sleeps 18
Distance to beach: 92 ft to Oak Bluffs Town Beach
Summer:
$20,800 - $38,800/wk
Off Season:
$16,800/wk
3
Oak Bluffs vacation rentals that sleep 16
Oak Bluffs
ID 5533
- 7 BR
- 4 baths
- Sleeps 16
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:
$26,100 - $33,100/wk
Off Season:
$11,100 - $26,100/wk
Oak Bluffs
ID 28357
- 6 BR
- 4 baths
- Sleeps 16
Beautiful, Newly Updated, Spacious 6 BR Home
Distance to beach: 3 miles to Oak Bluffs Inkwell Beach
4.817 reviews
Summer:
$15,000 - $21,000/wk
Off Season:
$11,000 - $16,000/wk
5
Oak Bluffs vacation rentals that sleep 15
Oak Bluffs
ID 11056
- 6 BR
- 2 baths
- Sleeps 15
Beach, Town, Tennis, Pickelball &Central AC,
Distance to beach: 3/10 mi to Inkwell Public Beach, Oak Bluffs
5.015 reviews
Summer:
$8,500 - $11,500/wk
Off Season:
$4,900 - $10,500/wk
5
Oak Bluffs vacation rentals that sleep 14
East Chop-Oak Bluffs
ID 14646
- 8 BR
- 3 baths
- Sleeps 14
Historic East Chop Beach House *300 ft to Jetty Beach
Distance to beach: 300 ft to Jetty Beach
4.710 reviews
Summer:
$12,550 - $15,300/wk
Off Season:
$12,550/wk
4
2 Pocasset Avenue, Oak Bluffs
ID 11813
- 7 BR
- 4 baths
- Sleeps 14
7 Bdrm In Town Walk to Beach
Distance to beach: 2.5 blocks Oak Bluffs Town Beach and 1.5 miles State Beach (Joseph Sylvia State Beach)
5.01 review
Summer:
$12,000 - $20,000/wk
Off Season:
$1,500 - $2,500/night
$8,000 - $12,000/wk
Oak Bluffs
ID 35126
- 7 BR
- 4 baths
- Sleeps 14
Historic Victorian Home With Ocean Views & AC
Distance to beach: 0.3 mile Oak Bluffs Town Beach
Summer:
$14,300 - $23,750/wk
Off Season:
$1,200 - $2,140/night
$9,650 - $15,350/wk
Oak Bluffs
ID 39105
- 5 BR
- 4 baths
- Sleeps 14
The Driftwood House Waterfront Retreat, Walk to the Inkwell
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
5.08 reviews
Summer:
$16,600 - $25,600/wk
Off Season:
$7,600 - $15,600/wk
4
Oak Bluffs vacation rentals that sleep 13
East Chop
ID 40722
- 7 BR
- 2 baths
- Sleeps 13
Spacious 7-Bedroom Vintage Cottage Near Town, Harbor & Beach
Distance to beach: 0.5 mi to The Jetty Beach and 1.0 mi to Inkwell Beach
Summer:
$4,400 - $6,900/wk
Off Season:
$500 - $600/night
$3,400 - $4,400/wk
4
Oak Bluffs
ID 35046
- 6 BR
- 2 baths
- Sleeps 13
Oak Bluffs Waterview Victorian (Air Conditioned & Linen)
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
5.019 reviews
Summer:
$8,500 - $11,675/wk
Off Season:
$4,000 - $7,550/wk
Oak Bluffs vacation rentals that sleep 12
East Chop
ID 23099
- 6 BR
- 4 baths
- Sleeps 12
Family Compound on East Chop
Distance to beach: 5 minute walk The Jetty Beach and two tenths mile to lovely Jetty Beach
4.67 reviews
Summer:
$6,500 - $8,600/wk
Off Season:
$3,000 - $6,500/wk
Oak Bluffs
ID 33717
- 6 BR
- 3 baths
- Sleeps 12
''The Carousel House'' - Ocean Park - Featured in NY Times
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$13,450 - $22,450/wk
Off Season:
$1,625/night
$11,925 - $13,450/wk
2
East Chop
ID 20680
- 6 BR
- 2 baths
- Sleeps 12
East Chop Martha’s Vineyard Waterfront Ocean View Rental
Distance to beach: 2/10 mile to Jetty Beach
5.02 reviews
Summer:
$7,250 - $8,250/wk
Off Season:
$5,250 - $7,750/wk
The Radcliffe House
ID 37237
- 6 BR
- 2 baths
- Sleeps 12
Beautiful newly renovated 6bd/ 3 block from beach
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
5.09 reviews
Summer:
$7,800 - $11,300/wk
Off Season:
$4,800 - $7,800/wk
Oak Bluffs
ID 38331
- 6 BR
- 3 baths
- Sleeps 12
6 Bedroom house for rent in Oak Bluffs, sleeps 12
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
Oak Bluffs
ID 41614
- 6 BR
- 6 baths
- Sleeps 12
Luxury Estate, 6 Bed 6.5 Bth, Infinity Pool, Spa, Water View
Distance to beach: 3.2 mi to Oak Bluffs Town Beach
Summer:
$52,650/wk
Off Season:
$37,650/wk
5
Oak Bluffs
ID 41948
- 6 BR
- 2 baths
- Sleeps 12
Bluff Breeze - 6BR Compound on East Chop in Oak Bluffs
Distance to beach: 0.6 mi to The Jetty Beach
Summer:
$9,020 - $16,020/wk
Off Season:
$1,000 - $2,000/night
$7,020 - $9,020/wk
Oak Bluffs
ID 32180
- 6 BR
- 3 baths
- Sleeps 12
6BR Victorian One Block from Ocean Park, Walk to Inkwell
Distance to beach: 500 ft Oak Bluffs Town Beach
Summer:
$11,160 - $15,905/wk
Off Season:
$500 - $1,340/night
$3,900 - $10,380/wk
Oak Bluffs (East Chop)
ID 11709
- 6 BR
- 4 baths
- Sleeps 12
Martha's Vineyard Memories, 1860 Sea Captain's Beach Home!
Distance to beach: 5 minute bike ride to Sunny Jetty Beach!
5.012 reviews
Off Season:
$5,999/wk
2
East Chop
ID 23424
- 6 BR
- 4 baths
- Sleeps 12
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
Off Season:
$600 - $1,500/night
$2,450 - $7,450/wk
4
Oak Bluffs
ID 37925
- 6 BR
- 4 baths
- Sleeps 12
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:
$19,250 - $21,250/wk
Off Season:
$1,371 - $2,928/night
$9,850 - $18,750/wk
5
Oak Bluffs
ID 11575
- 5 BR
- 3 baths
- Sleeps 12
Joy, historic 5 bedroom home in the heart Oak Bluffs
Distance to beach: 1/2 mile
5.01 review
Summer:
$500 - $600/night
$4,002 - $4,200/wk
Off Season:
$2,000 - $2,500/night
$500 - $4,200/wk
3
Oak Bluffs
ID 22593
- 5 BR
- 3 baths
- Sleeps 12
Charming 5+ BR Renovated Camp w/ Guest Cabin & Private Beach
Distance to beach: Private beach on the Lagoon
5.09 reviews
Off Season:
$450 - $900/night
$5,425/wk
6
Oak Bluffs
ID 26970
- 5 BR
- 2 baths
- Sleeps 12
AMENITIES GALORE, DOCK/TENNIS/AC IN PRIVATE COMMUNITY
Distance to beach: 3 miles to Joseph Sylvia State Beach
5.05 reviews
Summer:
$8,150 - $14,650/wk
Off Season:
$5,650 - $8,150/wk
2
Oak Bluffs
ID 31220
- 5 BR
- 2 baths
- Sleeps 12
CENTRAL AC! Walk 2 Town and Beach. Game room w/arcade games
Distance to beach: 1/2 mile to Jetty beach
16 reviews
Summer:
$6,500 - $8,000/wk
3
Harthaven
ID 31261
- 5 BR
- 3 baths
- Sleeps 12
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:
$9,500 - $11,000/wk
Off Season:
$7,500 - $10,500/wk
Oak Bluffs
ID 38997
- 5 BR
- 2 baths
- Sleeps 12
** Newly Renovated home 2 Minutes away from Circuit Ave
Distance to beach: 1.4 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
$7,900 - $9,350/wk
Off Season:
$500 - $700/night
$4,000 - $7,500/wk
4
East Chop
ID 37848
- 5 BR
- 5 baths
- 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
5.02 reviews
3
Lagoon Pond Salt-Waterfront
ID 27817
- 4 BR
- 3 baths
- Sleeps 12
Glorious Sunsets On and Over the Water. Beautiful Home
Distance to beach: Private beach, 3 kayak,4-SUPs, beach chairs & TOYS
5.031 reviews
OWNER SPECIAL:
2027: $2k/wk discount for family/group of 8 or fewer if booked by 11/30. Excludes wk of 8/7-14/27.
Summer:
$18,400 - $25,400/wk
Off Season:
$18,400/wk
11
Oak Bluffs
ID 37162
- 4 BR
- 2 baths
- Sleeps 12
Vineyard Seven/Sleeps 12/Tennis Courts/Centrally Located
Distance to beach: 2.7 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$7,500 - $14,500/wk
Off Season:
$428 - $1,142/night
$3,500 - $9,500/wk
Oak Bluffs vacation rentals that sleep 11
East Chop
ID 34693
- 5 BR
- 5 baths
- Sleeps 11
East Chop Beautiful Renovated Cottage, 5 Bedrooms + 5 Baths
Distance to beach: 7/10 mi to The Jetty Beach
5.05 reviews
Summer:
$8,350 - $12,100/wk
$42,000/mo
Off Season:
$1,500 - $2,000/night
$7,850/wk
6
Oak Bluffs
ID 33881
- 5 BR
- 1 bath
- Sleeps 11
Beach and downtown OB walkable! 5 Bedroom Victorian.
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
4.73 reviews
Summer:
$4,800 - $8,300/wk
Off Season:
$420 - $650/night
$3,250 - $4,800/wk
East Chop
ID 34601
- 4 BR
- 3 baths
- Sleeps 11
Dempster Park of East Chop: Walk to Beach & Town!
Distance to beach: Jetty Beach Oak Bluffs Town Beach
5.08 reviews
Summer:
$5,500 - $8,500/wk
Off Season:
$5,500 - $7,500/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
Distance to beach: 3/10 mi to Jetty Beach
4.88 reviews
Summer:
$6,500 - $11,500/wk
$42,000 - $46,000/mo
Off Season:
$1,300/night
$6,500 - $9,000/wk
2
Oak Bluffs
ID 29386
- 6 BR
- 2 baths
- Sleeps 10
Charming House on Waban Park, Walk to Beach, Town, & Ferry!
Distance to beach: 2 blocks from the Inkwell (Town Beach)
4.99 reviews
Summer:
$6,800 - $15,300/wk
Off Season:
$1,000/night
$4,300 - $5,300/wk
3
Oak Bluffs
ID 18823
- 6 BR
- 2 baths
- Sleeps 10
Charming, 6 Bedroom Victorian Gingerbread
Distance to beach: One block State Beach and One block to Sea View Ave & Town Beach.
4.913 reviews
Summer:
$8,300 - $9,900/wk
Off Season:
$8,300/wk
4
Oak Bluffs
ID 4132
- 5 BR
- 3 baths
- Sleeps 10
Waterfront with its own Private Sandy Beach ! ! !
Distance to beach: 0 feet to our beach; 1-1/2 miles to Vinyd beaches
4.97 reviews
Summer:
$7,900 - $9,800/wk
Off Season:
$4,000 - $7,000/wk
2
Oak Bluffs
ID 3540
- 5 BR
- 3 baths
- Sleeps 10
Magnificent Spacious Modern Home
Distance to beach: O.7 miles Oak Bluffs Town Beach and 0.7 miles Eastville Beach
4.79 reviews
Summer:
$6,500 - $8,500/wk
Off Season:
$3,000 - $6,500/wk
$3,500 - $4,000/mo
2
Oak Bluffs
ID 11040
Summer:
$5,070/wk
Off Season:
$1,970 - $4,670/wk
2
Oak Bluffs
ID 19414
- 5 BR
- 2 baths
- Sleeps 10
No need for car -- walk from ferry! Beach & water views
Distance to beach: ~30 yards to Inkwell Beach
5.03 reviews
Off Season:
$1,000 - $1,200/night
$8,450 - $9,950/wk
3
Oak Bluffs
ID 26885
- 5 BR
- 1 bath
- Sleeps 10
Great Location, Water Views, AC & Steps from Inkwell Beach
Distance to beach: 75 yards to the Inkwell beach
5.05 reviews
Summer:
$12,500/wk
Off Season:
$7,200 - $10,500/wk
Oak Bluffs
ID 27415
- 5 BR
- 2 baths
- Sleeps 10
Flex of travel around July 4th weekend. I.E. Sun-Sun or Mon
Distance to beach: Inkwell beach under a 1/2 mile
5.025 reviews
Summer:
$5,350 - $6,850/wk
Off Season:
$4,850 - $5,350/wk
3
Oak Bluffs
ID 28697
- 5 BR
- 3 baths
- Sleeps 10
Discover your perfect getaway! Book now!
Distance to beach: 0.2 Oak Bluffs Town Beach and Town / Inkwell Beach yards away
5.01 review
Summer:
$12,500 - $18,250/wk
Oak Bluffs
ID 33204
Summer:
$21,600 - $26,700/wk
$60,000 - $85,000/mo
Off Season:
$1,500 - $2,300/night
$13,800 - $23,800/wk
$35,000 - $75,000/mo
2
Oak Bluffs
ID 33370
- 5 BR
- 3 baths
- Sleeps 10
Central Air! Walk to town, Porch, 5 bedrooms & 3 bathrooms
Distance to beach: 15 minute walk to (5/10 of a mile) State Beach
4.621 reviews
Summer:
$9,500 - $13,000/wk
Off Season:
$8,000 - $10,000/wk
5
Oak Bluffs
ID 34051
- 5 BR
- 2 baths
- Sleeps 10
Fully Air-Conditioned 5BR East Chop Home, Walk to Beach
Distance to beach: 0.3 mi to The Jetty Beach
5.08 reviews
Summer:
$5,600 - $6,150/wk
Off Season:
$450 - $525/night
$3,400 - $3,750/wk
3
Historic Copeland District
ID 34083
- 5 BR
- 2 baths
- Sleeps 10
''The Legacy House'' - A Historic Beauty near beach & town
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
4.65 reviews
Summer:
$6,875 - $9,375/wk
Off Season:
$700 - $1,000/night
$4,875 - $6,975/wk
6
Oak Bluffs
ID 35217
- 5 BR
- 3 baths
- Sleeps 10
The “Summer Wind” House - Walk to the Beach!
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
$10,050 - $22,550/wk
Off Season:
$6,550 - $10,550/wk
Oak Bluffs
ID 34873
- 5 BR
- 2 baths
- Sleeps 10
5 BR , Walk to Town and Inkwell Beach, Sleeps 10
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Summer:
$11,250 - $13,250/wk
Off Season:
$10,000 - $11,250/wk
Waterview Farm
ID 38347
- 5 BR
- 2 baths
- Sleeps 10
Family Retreat in Private Setting
Distance to beach: 1/2mi Oak Bluffs Town Beach and 2 miles - State Beach
Summer:
$12,950 - $18,450/wk
Off Season:
$12,950 - $15,950/wk
7
Oak Bluffs
ID 38822
- 5 BR
- 4 baths
- Sleeps 10
Stylish In-town Gingerbread in the Center of EVERYTHING!
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
3 reviews
Summer:
$9,360 - $15,360/wk
Off Season:
$1,200/night
$6,360 - $7,360/wk
Oak Bluffs
ID 39273
- 5 BR
- 3 baths
- Sleeps 10
5 BR Victorian, AC, OCEAN PARK, FERRY,BEACHES,TOWN
Distance to beach: Across the Street to Town/Inkwell Beaches
Summer:
$11,000 - $17,000/wk
Off Season:
$10,500 - $12,500/wk
Oak Bluffs
ID 42050
- 5 BR
- 3 baths
- Sleeps 10
Serenity Ridge 5 BR Contemporary Ideal for Entertaining
Distance to beach: 2.3 mi to Oak Bluffs Town Beach
Summer:
$8,050 - $16,550/wk
Off Season:
$750 - $1,000/night
$5,550 - $8,050/wk
Oak Bluffs
ID 42177
- 5 BR
- 3 baths
- Sleeps 10
Oak Bluffs Colonial with Carriage House
Distance to beach: 1.2 mi to Oak Bluffs Town Beach
Summer:
$9,050 - $14,650/wk
Off Season:
$500 - $1,000/night
$7,650 - $9,050/wk
Oak Bluffs
ID 34390
- 5 BR
- 3 baths
- Sleeps 10
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
Off Season:
$5,500 - $7,500/wk
4
Oak Bluffs
ID 34661
- 5 BR
- 5 baths
- Sleeps 10
5 BR SUITES, SALT WATER POOL, CENTRAL AIR, BIKE PATH
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
Off Season:
$16,850 - $20,850/wk
Oak Bluffs
ID 35433
- 5 BR
- 4 baths
- Sleeps 10
Beautiful home, EV car charger, Outdoor BBQ, bar, fireplace
Distance to beach: 2.9 mi to Oak Bluffs Town Beach and 4.0 mi to State Beach
5.03 reviews
OWNER SPECIAL:
Across from Farm Neck Golf Course--Great for long golf weekends June and Sept.
Summer:
$8,385 - $10,085/wk
Off Season:
$650 - $950/night
$6,285 - $8,285/wk
3
Oak Bluffs
ID 42081
- 5 BR
- 2 baths
- Sleeps 10
NEW Rental- 5br Tuckernuck Home Walk to Ink Well
Distance to beach: 0.5 mi to Oak Bluffs Town Beach and .02 mi to Inkwell Beach
Summer:
$10,185 - $16,185/wk
Off Season:
$1,000 - $1,500/night
$6,685 - $11,185/wk
3
Oak Bluffs
ID 31349
- 4 BR
- 2 baths
- Sleeps 10
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
Summer:
$10,050 - $16,550/wk
Off Season:
$500 - $1,000/night
$5,550 - $9,550/wk
3
Oak Bluffs
ID 32791
- 4 BR
- 4 baths
- Sleeps 10
AIR CONDITIONED Spacious Beach House w/Attached Studio Apt.
Distance to beach: 1.8 mi To Oak Bluffs Town Beach
4.816 reviews
Summer:
$5,894 - $9,785/wk
Off Season:
$500/night
$4,692 - $5,894/wk
3
Oak Bluffs
ID 33878
- 4 BR
- 3 baths
- Sleeps 10
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
5.01 review
Summer:
$13,450 - $21,450/wk
Off Season:
$7,450 - $14,450/wk
5
Oak Bluffs
ID 33937
- 4 BR
- 2 baths
- Sleeps 10
Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
5.03 reviews
Summer:
$6,800 - $9,800/wk
Off Season:
$700/night
$4,265 - $6,300/wk
Oak Bluffs
ID 34079
- 4 BR
- 4 baths
- Sleeps 10
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:
$5,350 - $11,850/wk
Off Season:
$2,350 - $5,350/wk
6
Heart of Oak Bluffs
ID 34321
- 4 BR
- 5 baths
- Sleeps 10
Beautiful, Fully Renovated Gingerbread House on Ocean Park
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
5.08 reviews
Summer:
$12,600 - $22,600/wk
Off Season:
$8,600 - $10,600/wk
4
Oak Bluffs
ID 34157
- 4 BR
- 4 baths
- Sleeps 10
Waterfront Retreat with Pool and Lagoon Sunsets
Distance to beach: LAGOON WATERFRONT WITH PRIVATE BEACH
Summer:
$12,650 - $28,650/wk
Off Season:
$6,650 - $16,650/wk
Oak Bluffs
ID 37186
- 4 BR
- 3 baths
- Sleeps 10
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
5.05 reviews
Summer:
$7,385 - $10,385/wk
Off Season:
$550 - $800/night
$3,385 - $7,385/wk
5
Oak Bluffs
ID 38330
- 4 BR
- 2 baths
- Sleeps 10
The Tuck at Inkwell/Walk to Oak Bluffs Town Center & Beach
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
$6,700 - $10,350/wk
Off Season:
$4,350 - $5,850/wk
2
Oak Bluffs - Lagoon Pond
ID 37698
- 4 BR
- 2 baths
- Sleeps 10
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:
$14,500 - $18,500/wk
Off Season:
$800 - $1,500/night
$4,000 - $12,500/wk
6
Oak Bluffs
ID 39520
- 4 BR
- 4 baths
- Sleeps 10
Heated Pool/Spa/Poolhouse; Home Theatre, Outdoor Dining
Distance to beach: 2.2 mi to Oak Bluffs Town Beach
Summer:
$22,500 - $30,000/wk
Off Season:
$3,000 - $4,000/night
$20,000 - $22,500/wk
$85,000 - $90,000/mo
5
Oak Bluffs
ID 40927
- 4 BR
- 5 baths
- Sleeps 10
Best Kept Secret Retreat for Adults with Water & Golf Course
Distance to beach: 2.3 mi to Oak Bluffs Town Beach and 3.0 mi State Beach (Joseph Sylvia State Beach)
5 reviews
Summer:
$3,200/night
$18,800 - $26,300/wk
Off Season:
$2,500/night
$18,800/wk
Oak Bluffs, Martha's Vineyard
ID 41698
- 4 BR
- 3 baths
- Sleeps 10
Spacious Meadow View Farms Retreat in Oak Bluffs
Distance to beach: 3.1 mi to Oak Bluffs Town Beach and 3.4 mi to State Beach (Joseph Sylvia State Beach)
Summer:
$13,085 - $17,165/wk
Off Season:
$1,215 - $1,429/night
$9,515 - $11,045/wk
Oak Bluffs
ID 32194
- 4 BR
- 3 baths
- Sleeps 10
J. A. Norton House - Sun, Sea & Serenity in Oak Bluffs
Distance to beach: 1/10 mile Oak Bluffs Town Beach and 1 mile State Beach (Joseph Sylvia State Beach)
Off Season:
$5,400 - $6,900/wk
Oak Bluffs
ID 37145
- 4 BR
- 2 baths
- Sleeps 10
The Doll House - Your Dream Getaway on Martha’s Vineyard
Distance to beach: 2.8 mi to Oak Bluffs Town Beach
5.07 reviews
Summer:
$6,600 - $11,600/wk
Off Season:
$6,600/wk
5
Oak Bluffs vacation rentals that sleep 9
Vineyard Haven
ID 38413
- 5 BR
- 3 baths
- Sleeps 9
Charming Vineyard Haven Home near Lagoon Pond
Distance to beach: Short Distance to Lagoon Pond
East Chop
ID 42216
Summer:
$4,150 - $4,800/wk
Off Season:
$400 - $500/night
$3,300/wk
2
Oak Bluffs
ID 31591
- 4 BR
- 2 baths
- Sleeps 9
Oceanfront - steps to beach & town!
Distance to beach: 1/10 Oak Bluffs Town Beach and Oak Bluffs Town Beach (ocean) across the street
5.012 reviews
Summer:
$1,725 - $2,750/night
$13,875 - $19,125/wk
$45,000 - $85,000/mo
Off Season:
$1,000 - $2,200/night
$7,875 - $14,275/wk
$10,000 - $45,000/mo
5
Oak Bluffs
ID 29856
- 4 BR
- 3 baths
- Sleeps 9
Newly Renovated! Walk to Town Oak Bluffs 4 BR/3Bath A/C
Distance to beach: 1/2 m. to State Beach and 1/2 m. to East Chop Beach
Summer:
$7,700 - $12,700/wk
Off Season:
$850 - $1,000/night
$6,200 - $7,700/wk
Oak Bluffs
ID 38080
- 4 BR
- 4 baths
- Sleeps 9
East Chop, 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
5.015 reviews
OWNER SPECIAL:
I am offering a discount if you book for 2 weeks or more in July or August 2027.
Summer:
$8,250 - $16,750/wk
Off Season:
$7,050 - $7,750/wk
3
Oak Bluffs
ID 41751
- 4 BR
- 4 baths
- Sleeps 9
New Summer House with a Pool, Close to Town
Distance to beach: 1.3 mi to Oak Bluffs Town Beach and 1 mi to Eastville Beach
Summer:
$12,600 - $16,800/wk
Off Season:
$1,200 - $2,400/night
$5,000 - $10,500/wk
8
Oak Bluffs, Copeland Historic
ID 22456
- 4 BR
- 3 baths
- Sleeps 9
Solera - Ocean Views, Steps to Inkwell Beach
Distance to beach: Inkwell Beach is 1 short block away
5.022 reviews
Summer:
$8,425 - $16,925/wk
Off Season:
$850 - $1,100/night
$7,425 - $8,425/wk
$22,500/mo
7
Exquisite Waterfront Retreat w
ID 36784
- 4 BR
- 3 baths
- Sleeps 9
Exquisite Waterfront Retreat with Swimspa Pool
Distance to beach: 0.5 mi to State Beach and House is waterfront w/beach on Nantucket Sound.
Off Season:
$1,500 - $2,250/night
$12,500 - $15,000/wk
Oak Bluffs
ID 38650
- 4 BR
- 3 baths
- Sleeps 9
Cozy Cottage Near Inkwell Beach (Newer Build)
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
5.07 reviews
Summer:
$7,500 - $13,000/wk
Off Season:
$643 - $929/night
$3,800 - $6,500/wk
3
Oak Bluffs vacation rentals that sleep 8
Oak Bluffs
ID 32999
- 7 BR
- 2 baths
- Sleeps 8
In Town Oak Bluffs w/AC Beautifully Renovated Victorian
Distance to beach: 3/10 mile To Oak Bluffs Town Beach
5.011 reviews
Summer:
$13,075 - $18,575/wk
6
Lagoon Pond Estates, Oak Bluff
ID 34037
- 5 BR
- 3 baths
- Sleeps 8
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
4.73 reviews
Summer:
$5,950 - $7,950/wk
Off Season:
$429 - $785/night
$3,450 - $6,950/wk
6
Oak Bluffs
ID 42073
- 5 BR
- 4 baths
- Sleeps 8
Spacious 5 BR Oak Bluffs House - Large Yard & Outdoor Shower
Distance to beach: 0.8 mi to The Jetty Beach and 0.9 mi to Oak Bluffs Town Beach
1 review
Summer:
$5,950 - $13,200/wk
Off Season:
$675 - $800/night
$5,450 - $6,450/wk
Oak Bluffs
ID 25368
- 4 BR
- 3 baths
- Sleeps 8
Spacious retreat, just steps to Lagoon Beach - Great Value!!
Distance to beach: Lagoon Beach, approx. 500 feet
5.02 reviews
Summer:
$635 - $712/night
$4,540 - $5,280/wk
Off Season:
$540 - $630/night
$3,590 - $4,090/wk
5
Oak Bluffs
ID 12643
- 4 BR
- 2 baths
- Sleeps 8
Charming, Steps to Town & Beach, Central AC,
Distance to beach: 4/10th's of a mile Oak Bluffs Town Beach and 10 minute walk
5.016 reviews
Summer:
$6,800 - $7,800/wk
Off Season:
$3,500 - $6,800/wk
5
Oak Bluffs
ID 9007
- 4 BR
- 3 baths
- Sleeps 8
Spacious Contemporary Cape in Private Cul de Sac
Distance to beach: Ink Well 5 miles, State Beach 6, VH beaches 4
4.77 reviews
Summer:
$7,050/wk
Off Season:
$2,550 - $5,050/wk
$5,000 - $12,000/mo
Oak Bluffs
ID 26262
- 4 BR
- 1 bath
- Sleeps 8
La Sirena, The Mermaid Of Oak Bluffs
Distance to beach: less than a mile Oak Bluffs Town Beach
4.910 reviews
Summer:
$5,780 - $6,780/wk
Off Season:
$5,280 - $6,280/wk
4
Oak Bluffs
ID 29717
- 4 BR
- 2 baths
- Sleeps 8
Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
Distance to beach: Inkwell Beach approx. 1/2 a mile
4.97 reviews
Summer:
$750/night
$5,100 - $6,100/wk
$21,000 - $26,000/mo
Off Season:
$650/night
$5,100/wk
$20,000 - $20,400/mo
Oak Bluffs - Meadow View Farms
ID 29775
- 4 BR
- 4 baths
- Sleeps 8
Now booking for Spring - Summer 2027 !
Distance to beach: State Beach - 2 miles
4.935 reviews
Summer:
$5,063 - $8,497/wk
Off Season:
$700 - $950/night
$4,491 - $8,497/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
Distance to beach: Oak Bluffs State Beach and 1/2 mile to Oak Bluffs town beach, East Chop beach
5.05 reviews
Summer:
$6,000 - $10,000/wk
Off Season:
$700 - $1,000/night
$4,000 - $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!
Distance to beach: Under 1/2 mile to Inkwell, Jetty and Pay Beach
5.05 reviews
Summer:
$5,350 - $7,350/wk
Off Season:
$4,350 - $5,600/wk
$2,650/mo
6
Oak Bluffs
ID 30502
- 4 BR
- 2 baths
- Sleeps 8
Spacious, Relaxing & Central Location!
Distance to beach: 7-10 Minute Drive to OB & Edgartown Beaches
5.05 reviews
Summer:
$10,400 - $12,900/wk
Oak Bluffs
ID 30339
- 4 BR
- 2 baths
- Sleeps 8
Classic 4 B Cape in Eastville-Central AC & Heat!
Distance to beach: 1.5 miles Oak Bluffs Town Beach
5.08 reviews
Summer:
$5,075 - $6,175/wk
Off Season:
$4,175 - $5,675/wk
5
Oak Bluffs
ID 19178
- 4 BR
- 2 baths
- Sleeps 8
Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
Distance to beach: 2 Blocks Oak Bluffs Town Beach and 2 Blocks The Jetty Beach
5.07 reviews
Summer:
$7,000 - $18,500/wk
Off Season:
$2,500 - $5,000/wk
$3,000 - $10,000/mo
5
Oak Bluffs
ID 32817
- 4 BR
- 3 baths
- Sleeps 8
Exquisite family home - Ferry Tix, A/C,heated saltwater pool
Distance to beach: 1 and 2/10 mile Oak Bluffs Town Beach and 3 miles State Beach
5.09 reviews
Summer:
$11,100 - $17,600/wk
Off Season:
$6,100 - $8,600/wk
Oak Bluffs
ID 31301
- 4 BR
- 2 baths
- Sleeps 8
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:
$7,000 - $8,500/wk
Off Season:
$3,000 - $6,500/wk
Oak Bluffs
ID 32448
- 4 BR
- 2 baths
- Sleeps 8
Walk to Town/Walk to Beach in quiet location in OB (with AC)
Distance to beach: 3 blocks to Oak Bluffs Town Beach
5.05 reviews
Summer:
$8,400 - $12,400/wk
Off Season:
$7,400/wk
4
Oak Bluffs
ID 35109
Summer:
$20,650 - $25,850/wk
Off Season:
$2,000/night
$20,650/wk
3
Oak Bluffs
ID 35166
- 4 BR
- 2 baths
- Sleeps 8
Fully Renovated Victorian 4 Br /2.5 Baths Steps To Inkwell
Distance to beach: 0.1 mi to Oak Bluffs Town Beach
5.017 reviews
OWNER SPECIAL:
FALL SPECIAL REMAINING WEEKS IN SEP AND OCT 3850.
Summer:
$8,550 - $11,550/wk
Off Season:
$500 - $1,000/night
$3,950 - $8,550/wk
5
Oak Bluffs
ID 35279
- 4 BR
- 2 baths
- Sleeps 8
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:
$6,350 - $9,350/wk
Off Season:
$1,200 - $1,500/night
$5,350 - $6,350/wk
4
Oak Bluffs
ID 35483
- 4 BR
- 1 bath
- Sleeps 8
La Bella Sorella (The Beautiful Sister)
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
5.04 reviews
Summer:
$6,320 - $7,820/wk
Off Season:
$5,320 - $6,320/wk
3
Oak Bluffs
ID 28167
- 4 BR
- 3 baths
- Sleeps 8
Waterview Farms, Prime Bike Trails, Martha's Vineyard
Distance to beach: Water View Farms Landing
Summer:
$5,400 - $5,900/wk
Off Season:
$4,400/wk
Oak Bluffs
ID 35858
- 4 BR
- 2 baths
- Sleeps 8
BRENDA'S COTTAGE! Walk to town, screened porch, 4bds/2.5ba
Distance to beach: 15 minute walk to The Jetty Beach!
5.010 reviews
Summer:
$6,300 - $7,300/wk
Off Season:
$4,300 - $6,300/wk
5
Oak Bluffs
ID 34260
- 4 BR
- 2 baths
- Sleeps 8
Great central location, Central AC
Distance to beach: 4.0 mi to Oak Bluffs Town Beach
Summer:
$8,575 - $10,075/wk
Oak Bluffs
ID 37469
- 4 BR
- 2 baths
- Sleeps 8
Classic Victorian Beauty Steps to Beach
Distance to beach: 0.1 mi to Oak Bluffs Town Beach and Inkwell Beach
Summer:
$7,875 - $11,375/wk
Off Season:
$750 - $1,000/night
$6,875 - $8,375/wk
Oak Bluffs
ID 37484
- 4 BR
- 2 baths
- Sleeps 8
Nashawena Park Home- Close to Inkwell and town
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
Summer:
$7,300 - $11,300/wk
Off Season:
$500 - $1,000/night
$5,300 - $8,300/wk
3
Oak Bluffs
ID 38145
- 4 BR
- 3 baths
- Sleeps 8
Hideaway At Meadow View Farm/Private Tennis Courts
Distance to beach: 2.9 mi to Oak Bluffs Town Beach
5.05 reviews
Summer:
$9,150 - $9,500/wk
Off Season:
$3,900 - $9,150/wk
4
Oak Bluffs
ID 38181
- 4 BR
- 2 baths
- Sleeps 8
East Chop Cottage | Walk to Jetty Beach | A/C | Sleeps 8
Distance to beach: 0.6 mi to The Jetty Beach
5.04 reviews
Summer:
$6,000 - $7,500/wk
Off Season:
$875/night
$4,500 - $5,750/wk
Oak Bluffs
ID 38862
- 4 BR
- 2 baths
- Sleeps 8
Relaxing Oak Bluffs Getaway with A/C, Close to Town
Distance to beach: 0.9 mi to Oak Bluffs Town Beach
5.06 reviews
Summer:
$5,660 - $7,060/wk
Off Season:
$1,960 - $5,260/wk
1
Oak Bluffs
ID 38972
- 4 BR
- 3 baths
- Sleeps 8
Spacious Modern Vacation Rental, Great Getaway! BOOK NOW!
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
Summer:
$7,550 - $13,050/wk
Off Season:
$5,550 - $7,550/wk
Oak Bluffs
ID 38312
- 4 BR
- 2 baths
- Sleeps 8
Spacious Oak Bluffs Farmhouse
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$9,700 - $12,700/wk
Off Season:
$714/night
$6,700 - $8,700/wk
3
Oak Bluffs
ID 39654
- 4 BR
- 2 baths
- Sleeps 8
NOBLE HOUSE: Charming Oasis Near Town & Beach
Distance to beach: 1.2 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$8,100 - $11,400/wk
Off Season:
$700 - $1,100/night
$4,400 - $8,400/wk
$5,000 - $6,500/mo
3
Oak Bluffs
ID 39711
- 4 BR
- 1 bath
- Sleeps 8
Beachfront Oasis within Minutes from Downtown
Distance to beach: 2/10 mi (108 feet) Oak Bluffs Town Beach
Off Season:
$650/night
$4,710 - $7,710/wk
Oak Bluffs
ID 39688
Summer:
$6,800 - $8,800/wk
Off Season:
$600 - $1,000/night
$3,800 - $6,300/wk
Copeland/In Town
ID 39917
- 4 BR
- 1 bath
- Sleeps 8
In Town Victorian - Walk to Beach & Town
Distance to beach: 1/10 mi to Oak Bluffs Town Beach and inkwell The Jetty Beach
5.02 reviews
Summer:
$6,900 - $10,350/wk
Off Season:
$750 - $1,250/night
$2,400 - $6,400/wk
3
Oak Bluffs
ID 39932
- 4 BR
- 2 baths
- Sleeps 8
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
5.01 review
Summer:
$8,200 - $9,400/wk
Off Season:
$9,400/wk
3
East Chop
ID 41193
Summer:
$6,925 - $12,425/wk
Off Season:
$500 - $1,000/night
$4,425 - $7,925/wk
Oak Bluffs
ID 41262
- 4 BR
- 3 baths
- Sleeps 8
Sengekontacket Water View w/ Tennis and Pickleball
Distance to beach: 6 Miles State Beach
Summer:
$7,625 - $11,625/wk
Off Season:
$5,125 - $7,625/wk
East Chop
ID 41765
- 4 BR
- 2 baths
- Sleeps 8
The East Chop Hideaway w/ Air Condition; Walk to Beach/Town
Distance to beach: 0.4 mi to The Jetty Beach
5.01 review
Summer:
$6,400 - $7,400/wk
Off Season:
$800 - $1,000/night
$5,700 - $6,800/wk
1
East Chop
ID 41875
Summer:
$7,150 - $16,400/wk
Off Season:
$400 - $1,000/night
$6,620 - $7,625/wk
Lagoon Escape
ID 41907
Summer:
$9,400 - $18,150/wk
Off Season:
$800 - $1,500/night
$8,650 - $10,400/wk
Oak Bluffs
ID 41993
- 4 BR
- 2 baths
- Sleeps 8
Belledune- Vineyard Escape Close to Town
Distance to beach: 1.7 mi to Oak Bluffs Town Beach
Summer:
$4,050 - $5,750/wk
Off Season:
$400 - $800/night
$3,250 - $3,750/wk
Oak Bluffs
ID 42150
- 4 BR
- 4 baths
- Sleeps 8
Luxury Waterfront Home. Private Beach. Incredible Water View
Distance to beach: 1.5 mi to Inkwell Beach Oak Bluffs Town Beach and Direct access to 150 FT pvt beach on the lagoon
Summer:
$11,250 - $22,750/wk
Off Season:
$1,250 - $1,500/night
$4,750 - $12,750/wk
$10,000 - $12,000/mo
9
Oak Bluffs
ID 42164
Summer:
$8,218 - $11,518/wk
Off Season:
$5,218 - $8,218/wk
Oak Bluffs
ID 42179
- 4 BR
- 3 baths
- Sleeps 8
Oceanfront Cottage on East Chop with Private Dock & Mooring
Distance to beach: Steps from your private patio!
Summer:
$11,650 - $18,650/wk
Off Season:
$8,650 - $10,650/wk
Oak Bluffs
ID 42187
- 4 BR
- 1 bath
- Sleeps 8
Stunning Gingerbread Cottage in the Heart of Oak Bluffs
Distance to beach: 0.4 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$6,300 - $7,300/wk
Off Season:
$5,300/wk
Oak Bluffs
ID 42281
- 4 BR
- 3 baths
- Sleeps 8
Steps from the beach in Oak Bluffs
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
Summer:
$7,900 - $28,900/wk
East Chop
ID 28974
- 4 BR
- 2 baths
- Sleeps 8
Adorable Oak Bluffs Cottage with AC on East Chop
Distance to beach: 1/2 mile to Eastville Beach
5.06 reviews
Summer:
$4,950 - $5,650/wk
Off Season:
$550 - $600/night
$3,850 - $3,900/wk
4
Oak Bluffs
ID 31304
- 4 BR
- 2 baths
- Sleeps 8
Classic waterfront Vict. cottage, walk to town; huge porch
Distance to beach: Two blocks to Inkwell & OB town beach, Harthaven
5.018 reviews
Summer:
$1,200 - $1,700/night
$8,850 - $12,350/wk
Off Season:
$500 - $1,200/night
$3,950 - $9,550/wk
$6,500/mo
3
Waban Alley Park
ID 25820
- 4 BR
- 2 baths
- Sleeps 8
Water-view Victorian on Waban-Alley Park, Sleeps 7- 8
Distance to beach: 1/10 mile to Inkwell/Oak Bluffs beaches
5.01 review
Summer:
$5,200 - $5,600/wk
Off Season:
$5,000 - $5,400/wk
4
Oak Bluffs
ID 33286
- 4 BR
- 2 baths
- Sleeps 8
Lagoon Chic 4 Bedroom Family Home
Distance to beach: 500 steps Eastville Beach and Inkwell Beach 1.2 miles
4.815 reviews
Off Season:
$3,350 - $4,550/wk
3
Oak Bluffs
ID 32868
- 4 BR
- 2 baths
- Sleeps 8
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 IS OPEN , 1ST 2 WEEKS OF JULY, AND THE LAST WEEK OF AUGUST 2026.
Off Season:
$8,100/wk
Sengekontacket Association, Oa
ID 37096
- 4 BR
- 2 baths
- Sleeps 8
Sun Filled Waterfront Home with a Beautiful Pond View
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
5.03 reviews
Off Season:
$500 - $560/night
$4,901 - $5,001/wk
Oak Bluffs - Sleeps 8, near Fa
ID 37842
2
East Chop Highlands
ID 39326
- 4 BR
- 2 baths
- Sleeps 8
Cozy Cottage at Coleman Corners/Walk to Beach
Distance to beach: 1/2 mi to The Jetty Beach
5.011 reviews
Off Season:
$3,700 - $4,700/wk
3
Oak Bluffs
ID 39877
- 4 BR
- 4 baths
- Sleeps 8
Chic Contemporary Close to Downtown
Distance to beach: 3.1 mi to Oak Bluffs Town Beach
Off Season:
$7,550 - $8,050/wk
Oak Bluffs
ID 41615
- 4 BR
- 2 baths
- Sleeps 8
Close to Town, Beautifully Updated
Distance to beach: 1.3 miles Oak Bluffs Town Beach and 3 miles to State Beach
Off Season:
$395 - $600/night
$2,750 - $3,850/wk
$7,500 - $9,500/mo
3
Oak Bluffs
ID 35115
- 3 BR
- 3 baths
- Sleeps 8
Experience A Luxury Getaway By The Lagoon
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
Summer:
$7,600 - $14,000/wk
Off Season:
$600 - $900/night
$4,600 - $6,950/wk
2
Historic Copeland District
ID 35575
- 3 BR
- 2 baths
- Sleeps 8
The Cinderella Cottage Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach and Steps to Inkwell Beach
5.01 review
Off Season:
$1,000 - $2,000/night
$7,850/wk
5
Oak Bluffs
ID 38157
- 3 BR
- 2 baths
- Sleeps 8
Endless Summer Vacation
Distance to beach: 0.7 mi to The Jetty Beach and 1 mile to Inkwell Beach
5.011 reviews
Summer:
$4,950 - $8,650/wk
Off Season:
$500 - $1,000/night
$3,950 - $5,950/wk
Central Oak Bluffs
ID 39959
- 3 BR
- 3 baths
- Sleeps 8
Charming Farmhouse with Central A/C Close to Town
Distance to beach: 1.1 mi to The Jetty Beach
Summer:
$6,300 - $8,300/wk
Off Season:
$600 - $800/night
$4,300 - $5,800/wk
Oak Bluffs
ID 40323
- 3 BR
- 2 baths
- Sleeps 8
Chic Coastal Escape - The Retreat at Towanticut
Distance to beach: 1.0 mi to The Jetty Beach
5.010 reviews
Summer:
$700 - $1,200/night
$7,000 - $9,450/wk
Off Season:
$400 - $900/night
$3,500 - $6,500/wk
4
Heritage Haven
ID 40508
- 3 BR
- 3 baths
- Sleeps 8
Heritage Haven: AC, Steps to Town, Beach and Parks
Distance to beach: 0.4 mi to Oak Bluffs Town Beach
5.03 reviews
OWNER SPECIAL:
Fall and Winter Getaway Discount - Save 10%.
Summer:
$8,200 - $12,150/wk
Off Season:
$5,100 - $8,200/wk
6
Oak Bluffs
ID 40672
- 3 BR
- 2 baths
- Sleeps 8
3 Bedroom/Sleeper Den: Walk to Town with Pool and Hot Tub
Distance to beach: 0.9M Oak Bluffs Town Beach and 1.5M The Jetty Beach
Summer:
$8,150 - $10,150/wk
Off Season:
$5,950 - $7,150/wk
Oak Bluffs
ID 40827
- 3 BR
- 2 baths
- Sleeps 8
Downtown Oak Bluffs Charmer
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
$5,400 - $9,900/wk
Off Season:
$500 - $900/night
$3,900 - $7,200/wk
5
Oak Bluffs
ID 41020
- 3 BR
- 2 baths
- Sleeps 8
Delightful 3 BR Retreat Near Lagoon Pond and Oak Bluffs
Distance to beach: 500ft to Lagoon Pond;1.5mi to Oak Bluffs Town Bch
5.09 reviews
Summer:
$6,650 - $8,050/wk
Off Season:
$700/night
$5,250 - $5,950/wk
3
Oak Bluffs
ID 41051
- 3 BR
- 1 bath
- Sleeps 8
Casa Luca: Near Beach/Town, Pets Welcome, Outdoor Shower
Distance to beach: 1.2 mi to Oak Bluffs Town Beach
5.020 reviews
Summer:
$6,660 - $12,990/wk
Off Season:
$189 - $790/night
$1,990 - $6,660/wk
4
Oak Bluffs
ID 41439
Summer:
$5,500 - $8,500/wk
Off Season:
$4,000 - $5,500/wk
Oak Bluffs
ID 41636
- 3 BR
- 2 baths
- Sleeps 8
Updated Coastal OB Retreat | AC, Walk to Town + Patio
Distance to beach: 3.1 State Beach and .4 mi to Eastville Beach
5.02 reviews
Summer:
$5,910 - $8,010/wk
Off Season:
$450 - $650/night
$4,510 - $6,510/wk
5
Oak Bluffs
ID 31356
- 3 BR
- 4 baths
- Sleeps 8
Ellen’s Cape: Up-island convenience, down-island tranquility
Distance to beach: 3.8 mi to Oak Bluffs Town Beach and 4.0 mi to State Beach (Joseph Sylvia State Beach)
5 reviews
Off Season:
$575 - $1,400/night
$4,425 - $7,400/wk
6
Oak Bluffs
ID 40570
- 3 BR
- 2 baths
- Sleeps 8
Comfortable, Family-Friendly Home w/ Spacious Deck, Fire Pit
Distance to beach: 1 mile The Jetty Beach and 1 mile Eastville Beach
Off Season:
$400 - $500/night
$2,800 - $5,800/wk
5
Oak Bluffs
ID 41077
- 3 BR
- 2 baths
- Sleeps 8
Jessie Lee Legacy House: Rest and Restore in Oak Bluffs
Distance to beach: 1.1 mi to Oak Bluffs Town Beach
Off Season:
$4,900/wk
Oak Bluffs vacation rentals that sleep 7
Oak Bluffs
ID 6969
- 4 BR
- 2 baths
- Sleeps 7
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:
$4,500/wk
Off Season:
$2,300/wk
East Chop
ID 35529
- 4 BR
- 1 bath
- Sleeps 7
Quiet, Comfy Home in Heart of East Chop - walk to the beach!
Distance to beach: 0.5 mi to The Jetty Beach
4.912 reviews
Summer:
$4,300 - $5,400/wk
$15,000/mo
Off Season:
$3,400 - $4,300/wk
3
Oak Bluffs
ID 6897
- 3 BR
- 1 bath
- Sleeps 7
Comfortable Cape within walking distance to Downtown
Distance to beach: Jetty Beach The Jetty Beach and 8/10 miles to Oak Bluffs Town Beach
4.69 reviews
Summer:
$4,200 - $4,500/wk
Off Season:
$3,200 - $3,600/wk
Historic Downtown Copeland Dis
ID 13640
- 3 BR
- 2 baths
- Sleeps 7
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 - $4,100/wk
Off Season:
$3,300 - $3,800/wk
6
Oak Bluffs
ID 21147
- 3 BR
- 2 baths
- Sleeps 7
Oak Bluffs ''Quaint Victorian Home''
Distance to beach: One and a quarter mile State Beach
4.54 reviews
Summer:
$3,100 - $4,200/wk
$10,000/mo
Off Season:
$2,500 - $3,100/wk
$8,000 - $10,000/mo
5
Oak Bluffs
ID 33550
- 3 BR
- 3 baths
- Sleeps 7
Our great Guest Review's tell it all!
Distance to beach: 2 miles Oak Bluffs Town Beach and 1.5 Eastville Beach
5.030 reviews
Summer:
$6,550 - $8,650/wk
Off Season:
$6,350/wk
7
Oak Bluffs
ID 32945
- 3 BR
- 2 baths
- Sleeps 7
Walk to Private Lagoon Beach PET FRIENDLY 2026 DATES OPEN
Distance to beach: Short walk to deeded beach
Summer:
$4,800 - $6,300/wk
Off Season:
$500 - $1,000/night
$3,300 - $4,300/wk
Oak Bluffs-MCVMA
ID 35732
- 3 BR
- 1 bath
- Sleeps 7
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
4.911 reviews
Summer:
$6,800 - $8,295/wk
Off Season:
$3,250/wk
4
Oak Bluffs
ID 39601
- 3 BR
- 2 baths
- Sleeps 7
Oak Bluffs: Close to town and beaches, pet friendly w/ pool
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
Summer:
$13,600 - $19,600/wk
4
Vineyard Hills
ID 39962
- 3 BR
- 2 baths
- Sleeps 7
Oak Bluffs Escape - Close to Town and Beaches!
Distance to beach: 2.7 mi to Oak Bluffs Town Beach
14 reviews
Summer:
$6,040 - $8,325/wk
Off Season:
$349 - $850/night
$2,935 - $5,825/wk
Oak Bluffs
ID 40899
- 3 BR
- 1 bath
- Sleeps 7
Robin's Nest; Minutes to Oak Bluffs, Beaches & Lagoon Pond
Distance to beach: 2.5 mi to Oak Bluffs Town Beach and 4 mi to State Beach
3 reviews
Summer:
$5,150 - $5,950/wk
Off Season:
$660/night
$4,970/wk
Historic Copeland District
ID 42122
- 3 BR
- 2 baths
- Sleeps 7
Perfect! 7 Houses from the Beach-Walk to Ferry & Town!
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
Summer:
$7,500 - $10,000/wk
$19,000 - $24,000/mo
Off Season:
$850 - $1,500/night
$2,500 - $7,500/wk
$12,000 - $28,000/mo
Gingerbred Cottages - MVCMA
ID 38584
- 3 BR
- 1 bath
- Sleeps 7
Gingerbread Cottage Walk to Town (June-July-1 wk of August)
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$5,900 - $8,900/wk
Off Season:
$5,400/wk
5
Oak Bluffs
ID 28887
- 2 BR
- 1 bath
- Sleeps 7
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
4.915 reviews
Summer:
$4,200 - $5,800/wk
Off Season:
$3,900 - $4,200/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
Distance to beach: 1/4 mile The Jetty Beach and 1/2 mile Oak Bluffs Town Beach
5.05 reviews
Summer:
$9,607 - $10,607/wk
$36,000 - $40,000/mo
Off Season:
$6,107 - $9,607/wk
$19,500 - $36,000/mo
3
Oak Bluffs
ID 12452
- 3 BR
- 1 bath
- Sleeps 6
Easy and comfortable Island home
Distance to beach: 1/4 mile Eastville Beach and 1/2 mile to Jetty Beach
4.910 reviews
Summer:
$4,050 - $4,200/wk
Off Season:
$400 - $600/night
$2,700 - $3,700/wk
5
Oak Bluffs
ID 21790
- 3 BR
- 1 bath
- Sleeps 6
Ideal location, short walk to Town & Beach
Distance to beach: 7 min walk Oak Bluffs Town Beach and 7-minute walk to Inkwell Beach
5.011 reviews
Summer:
$4,040 - $5,040/wk
Off Season:
$450 - $500/night
$2,740 - $4,240/wk
Oak Bluffs
ID 22799
- 3 BR
- 3 baths
- Sleeps 6
MV Peace of Pie - Short 15 min walk to OB center, AC
Distance to beach: 1.1 miles to Oak Bluffs Town Beach
5.016 reviews
Summer:
$5,850 - $7,350/wk
Off Season:
$6,350/wk
Oak Bluffs
ID 20575
- 3 BR
- 3 baths
- Sleeps 6
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
Off Season:
$1,300 - $5,300/wk
$3,500 - $14,000/mo
Oak Bluffs
ID 19888
- 3 BR
- 3 baths
- Sleeps 6
Beautiful Sunny w/Lagoon View-Walk to Center of Oak Bluffs
Distance to beach: 130 feet (steps) from the house
5.05 reviews
Summer:
$2,650 - $3,900/wk
Off Season:
$2,000 - $2,750/wk
$2,000 - $7,800/mo
32 County Road, Oak Bluffs
ID 31344
- 3 BR
- 2 baths
- Sleeps 6
OB-POSH with Central A/C
Distance to beach: Eastville Beach about 1/2 a mile
3 reviews
Summer:
$6,800 - $8,800/wk
Off Season:
$4,350/wk
2
Oak Bluffs
ID 33125
- 3 BR
- 2 baths
- Sleeps 6
Cozy Sunlit Cottage, quick walk to downtown Oak Bluffs!
Distance to beach: 1 mile To Oak Bluffs Town Beach
5.07 reviews
Summer:
$4,250 - $5,000/wk
Off Season:
$350 - $450/night
$2,400 - $4,000/wk
Near MV Hospital
ID 33461
- 3 BR
- 1 bath
- Sleeps 6
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
Off Season:
$2,300/wk
East Chop
ID 32946
- 3 BR
- 2 baths
- Sleeps 6
Newly Renovated East Chop Home. Walk to beach and town!
Distance to beach: 3/10 mi To The Jetty Beach
5.017 reviews
Summer:
$5,295 - $5,595/wk
Off Season:
$4,295 - $4,795/wk
5
Walk to town- quiet location
ID 33701
- 3 BR
- 2 baths
- Sleeps 6
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
4.52 reviews
Summer:
$3,950 - $4,950/wk
Oak Bluffs
ID 34172
- 3 BR
- 3 baths
- Sleeps 6
A Vineyard Escape with A/C, Tennis, Golf & Easy Beach Access
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
5.013 reviews
Summer:
$2,450 - $6,750/wk
Off Season:
$650/night
$3,000 - $5,000/wk
3
Oak Bluffs
ID 34548
- 3 BR
- 2 baths
- Sleeps 6
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:
$4,200 - $4,900/wk
$20,000/mo
Off Season:
$400 - $500/night
$3,900 - $4,200/wk
8
Oak Bluffs
ID 34180
- 3 BR
- 2 baths
- Sleeps 6
A/C, Assoc. tennis/pickleball courts + dock
Distance to beach: 3 & 4/10 mi Oak Bluffs Town Beach and 5 miles State Beach
5.03 reviews
Summer:
$4,300 - $8,300/wk
Off Season:
$2,800 - $4,300/wk
Oak Bluffs
ID 37557
- 3 BR
- 2 baths
- Sleeps 6
Pristine Home in Oak Bluffs/Close to Downtown
Distance to beach: 1 mi to Eastville Beach and 1.2 mi to Inkwell Beach
5.05 reviews
Summer:
$7,730 - $12,826/wk
Off Season:
$1,282 - $8,770/wk
Oak Bluffs
ID 35664
- 3 BR
- 3 baths
- Sleeps 6
Perfect Martha’s Vineyard Getaway – Walk to Lagoon
Distance to beach: 2 blks to Lagoon Pond;1mi to Oak Bluffs Town Beach
5.04 reviews
Summer:
$4,300 - $5,800/wk
Off Season:
$2,800/wk
2
Oak Bluffs
ID 34484
- 3 BR
- 3 baths
- Sleeps 6
Charming MV Waterfront Cottage on the Lagoon ~ Sleeps 6
Distance to beach: Sandy waterfront, 1/2 mile to Eastville Beach
Summer:
$5,925 - $6,925/wk
Oak Bluffs
ID 38623
- 3 BR
- 1 bath
- Sleeps 6
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
5.05 reviews
Summer:
$5,100 - $9,100/wk
Off Season:
$4,500 - $5,700/wk
Oak Bluffs
ID 37961
Off Season:
$428/night
$3,300 - $3,800/wk
Oak Bluffs
ID 39483
- 3 BR
- 2 baths
- Sleeps 6
Top Notch Vacation Rentals (Walk to Sengekontacket Pond)
Distance to beach: 1 mi to Oak Bluffs Town Beach and 5 min walk to Sengekontacket Pond
Summer:
$5,675 - $8,175/wk
Off Season:
$780/night
$4,675 - $6,675/wk
Oak Bluffs Highlands
ID 39616
- 3 BR
- 3 baths
- Sleeps 6
Oak Bluffs Highlands Modern Retreat w/ Detached Studio!
Distance to beach: 1 mi Oak Bluffs Town Beach and 1.2 mi to Eastville Beach
5.06 reviews
Summer:
$3,475 - $5,475/wk
Off Season:
$2,975 - $4,475/wk
11
Oak Bluffs
ID 40097
- 3 BR
- 2 baths
- Sleeps 6
Beautiful and Remodeled in Prime Location
Distance to beach: 2.1 mi to Oak Bluffs Town Beach
Summer:
$4,800 - $6,300/wk
Off Season:
$570 - $640/night
$4,300 - $5,300/wk
3
Oak Bluffs
ID 40164
- 3 BR
- 3 baths
- Sleeps 6
Gorgeous Home in Oak Bluffs in Ultra-Convenient Location!
Distance to beach: 0.5 mi to Oak Bluffs Town Beach and Inkwell Beach
5.01 review
Off Season:
$700/night
$5,250 - $6,650/wk
5
Oak Bluffs
ID 40831
- 3 BR
- 1 bath
- Sleeps 6
Victorian Cottage by Sunset Lake/Walk to Town, Beach & Ferry
Distance to beach: 0.5 mi to The Jetty Beach
8 reviews
Summer:
$4,250 - $6,200/wk
Off Season:
$375 - $500/night
$2,000 - $3,750/wk
1
Oak Bluffs
ID 41733
- 3 BR
- 2 baths
- Sleeps 6
Charming Home in Oak Bluffs Close to Town
Distance to beach: 1.0 mi to The Jetty Beach
Summer:
$6,400 - $9,400/wk
Off Season:
$500 - $1,000/night
$4,400 - $6,400/wk
Oak Bluffs
ID 41896
- 3 BR
- 2 baths
- Sleeps 6
Charming 3 Bedroom Apartment in Oak Bluffs
Distance to beach: 1.8 mi to Oak Bluffs Town Beach
Summer:
$5,100 - $7,400/wk
Off Season:
$4,575/wk
Steps to downtown OB
ID 41942
- 3 BR
- 1 bath
- Sleeps 6
Cottage Steps from Boats, Downtown & Beaches, No Car Needed
Distance to beach: 0.7 mi to Oak Bluffs Town Beach
5.01 review
Off Season:
$400 - $500/night
$3,725/wk
Oak Bluffs
ID 41968
- 3 BR
- 2 baths
- Sleeps 6
Vineyard Charm with private beach Pet Friendly
Distance to beach: 1.6 mi to Oak Bluffs Town Beach and Steps to to private deeded beach
Summer:
$500 - $900/night
$5,800 - $6,800/wk
Off Season:
$4,300 - $5,300/wk
Oak Bluffs
ID 42002
- 3 BR
- 2 baths
- Sleeps 6
Beautiful 3 Bedroom 2 Bath Cape Cod Style Home - Oak Bluffs
Distance to beach: 2.0 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$6,800 - $9,300/wk
Off Season:
$700 - $850/night
$4,300 - $6,800/wk
Lagoon Estates
ID 42080
Summer:
$4,950 - $5,950/wk
Off Season:
$550/night
$3,150 - $4,750/wk
5
Oak Bluffs
ID 42307
- 3 BR
- 2 baths
- Sleeps 6
Walk to Private Lagoon Beach-Close to Town
Distance to beach: 1.6 mi to Oak Bluffs Town Beach
Summer:
$5,150 - $6,350/wk
Off Season:
$400 - $700/night
$4,850 - $5,150/wk
East Chop
ID 42222
- 3 BR
- 1 bath
- Sleeps 6
Andorra Cottage; Classic Oak Bluffs Cottage
Distance to beach: 0.7 mi to The Jetty Beach
Summer:
$3,600/wk
Off Season:
$2,800 - $3,600/wk
2
Oak Bluffs
ID 9098
- 3 BR
- 2 baths
- Sleeps 6
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
Off Season:
$5,250/wk
Oak Bluffs
ID 9028
- 3 BR
- 2 baths
- Sleeps 6
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
4.818 reviews
Summer:
$3,900 - $4,900/wk
$14,500 - $15,000/mo
Off Season:
$3,200 - $3,900/wk
$10,000 - $15,000/mo
4
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
Distance to beach: Lagoon Beach 1/2 mile, Eastville Beach < 1 mile
4.911 reviews
6
Oak Bluffs
ID 24822
- 3 BR
- 2 baths
- Sleeps 6
Private Oak Bluffs Retreat - Central AC - Patio & Fire Pit
Distance to beach: 3 miles Oak Bluffs Town Beach and Less than 2 miles to Sailing Camp Park
5.030 reviews
Summer:
$5,975 - $8,075/wk
Off Season:
$775/night
$5,275 - $5,975/wk
6
Oak Bluffs
ID 32157
- 3 BR
- 2 baths
- Sleeps 6
Charming Home On Farm Pond w/ Ocean View walk to Inkwell
Distance to beach: 4/10 mile to Inkwell Beach
1 review
Summer:
$4,150 - $7,250/wk
Off Season:
$3,000 - $3,250/wk
2
Oak Bluffs
ID 37210
- 3 BR
- 1 bath
- Sleeps 6
Birds of Paradise - Walk to Beaches and Town
Distance to beach: 1/2 mi to Oak Bluffs Town Beach
Off Season:
$2,950 - $3,450/wk
2
Oak Bluffs
ID 37987
- 3 BR
- 2 baths
- Sleeps 6
Renovated Cottage in Convenient Location to Beaches and Town
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$430/night
$3,200 - $4,200/wk
Off Season:
$325 - $400/night
$2,700 - $4,200/wk
$8,000/mo
Oak Bluffs
ID 38836
- 3 BR
- 1 bath
- Sleeps 6
Oak Bluffs Victorian Gingerbread Cottage
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
Oak Bluffs
ID 40495
- 3 BR
- 2 baths
- Sleeps 6
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
Off Season:
$700 - $750/night
$3,800 - $5,100/wk
$4,500 - $16,000/mo
3
Oak Bluffs
ID 41191
- 3 BR
- 2 baths
- Sleeps 6
Charming and Centrally located Oak Bluffs Cottage
Distance to beach: 3.5 Oak Bluffs Town Beach and 3.5 South Beach - Katama
Off Season:
$3,850 - $4,350/wk
2
LAGOON POND WATERFRONT
ID 40593
- 3 BR
- 3 baths
- Sleeps 6
Lagoon Waterfront with Amazing Sunsets
Distance to beach: Lagoon Pond Waterfront Beach is included
Off Season:
$800/night
$6,150 - $9,150/wk
Oak Bluffs
ID 41890
- 3 BR
- 1 bath
- Sleeps 6
NEW! Charming Oak Bluffs Coastal Retreat -Sleeps 8
Distance to beach: 2.8 mi to Tisbury Town Beach
Summer:
$6,500 - $8,000/wk
Off Season:
$500 - $642/night
$3,000 - $6,000/wk
Ocean Park Renovated Home
ID 41979
- 3 BR
- 2 baths
- Sleeps 6
New to the rental market - Ocean Park 3 Bedroom Home!
Distance to beach: 0.2 mi to Oak Bluffs Town Beach and Inkwell Beach
Summer:
$10,650 - $14,150/wk
Off Season:
$500 - $1,000/night
$5,650 - $12,650/wk
Oak Bluffs
ID 33919
- 2 BR
- 2 baths
- Sleeps 6
Oak Bluffs Retreat - The perfect getaway!
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
5.02 reviews
Summer:
$3,620 - $5,285/wk
Off Season:
$480 - $580/night
$3,585 - $4,285/wk
In-Town of Oak Bluffs
ID 36162
- 2 BR
- 3 baths
- Sleeps 6
Charming Cottage in Great OB Location
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
5.01 review
Summer:
$5,875 - $6,575/wk
Off Season:
$500 - $1,000/night
$5,375 - $5,875/wk
3
Oak Bluffs
ID 27087
Off Season:
$1,750 - $1,950/wk
Oak Bluffs vacation rentals that sleep 5
Oak Bluffs
ID 42074
- 3 BR
- 1 bath
- Sleeps 5
East Chop Cottage Walking Distance to OB and Town Beaches
Distance to beach: .04 Oak Bluffs Town Beach and .03 The Jetty Beach
OWNER SPECIAL:
No Lodging Tax!! Save over $1,300/week in taxes; First 2 weeks in Aug 2027 Available IDEAL LOCATION
Summer:
$9,300/wk
6
Oak Bluffs
ID 16588
- 3 BR
- 1 bath
- Sleeps 5
Vanessa's Hide-Away; ferry res. avail. 7/29-8/5
Distance to beach: 2 minute walk to Oak Bluffs Beaches
4.714 reviews
Off Season:
$4,270/wk
Oak Bluffs
ID 41061
- 3 BR
- 2 baths
- Sleeps 5
Sarah's Cottage - 100 Yards to Bus Stop & Bike Path
Distance to beach: 1.4 mi to Oak Bluffs Town Beach
Off Season:
$400 - $500/night
$4,280/wk
$11,000/mo
Oak Bluffs
ID 36583
- 2 BR
- 2 baths
- Sleeps 5
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:
$7,325 - $8,325/wk
Off Season:
$500 - $850/night
$4,325 - $5,325/wk
Oak Bluffs
ID 39369
- 2 BR
- 1 bath
- Sleeps 5
Quintessential Vineyard A-Frame near Oak Bluffs Center (2BR)
Distance to beach: 0.5 miles to Lagoon Pond Public Access Beach
5.012 reviews
Summer:
$4,310 - $4,810/wk
Off Season:
$350 - $525/night
$2,710 - $4,310/wk
2
Oak Bluffs vacation rentals that sleep 4
Oak Bluffs
ID 35127
- 2 BR
- 2 baths
- Sleeps 4
Charming Cottage Located in Heart of Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
Summer:
$5,575 - $9,250/wk
Off Season:
$428 - $715/night
$3,125 - $5,925/wk
Oak Bluffs on the Edgartown li
ID 37184
- 2 BR
- 1 bath
- Sleeps 4
Quiet, Clean, and Close to all 3 down-island towns
Distance to beach: 5.5 miles State Beach and 7 miles South Beach - Katama
5.01 review
Summer:
$3,225 - $3,525/wk
$13,000 - $16,000/mo
Off Season:
$3,225/wk
East Chop
ID 38085
- 2 BR
- 1 bath
- Sleeps 4
Gorgeous Waterfront A-Frame on East Chop
Distance to beach: 0.5 mi to The Jetty Beach and 1 mile to Inkwell Beach State Beach
4.98 reviews
Summer:
$6,400 - $8,400/wk
$25,000 - $35,000/mo
Off Season:
$2,400 - $6,400/wk
$18,000/mo
7
Oak Bluffs
ID 17574
- 2 BR
- 1 bath
- Sleeps 4
Walk to Sailing Camp Beach – Nature Trails & Serene Backyard
Distance to beach: 200yd to Sailing Camp beach. 2.1m to Inkwell beach
5.04 reviews
Off Season:
$415 - $500/night
$2,500 - $2,895/wk
4
Oak Bluffs
ID 40983
- 2 BR
- 1 bath
- Sleeps 4
Spacious 2 Bedroom/Walk to Harbor, Beach, Ferry & Town
Distance to beach: 0.5 mi to The Jetty Beach
5.02 reviews
Summer:
$2,950 - $4,350/wk
Off Season:
$300 - $386/night
$2,250 - $2,750/wk
2
Oak Bluffs
ID 41866
Summer:
$4,700 - $6,200/wk
Off Season:
$400 - $750/night
$4,200/wk
Oak Bluffs
ID 42285
- 2 BR
- 1 bath
- Sleeps 4
Arrowsmith Cottage: Cozy Oak Bluffs Getaway Near the Beach
Distance to beach: 0.9 mile Eastville Beach
6 reviews
Summer:
$4,022 - $5,022/wk
Off Season:
$195 - $500/night
$1,987 - $4,022/wk
Oak Bluffs
ID 22568
- 2 BR
- 2 baths
- Sleeps 4
Charming two bedroom house near golf course and bike path
Distance to beach: 1 mile to Inkwell and Town Beaches
5.04 reviews
Summer:
$3,825 - $4,575/wk
Off Season:
$4,325/wk
9
Oak Bluffs
ID 36682
- 1 BR
- 1 bath
- Sleeps 4
Ocean facing Guest House, The Lilac House
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
5.02 reviews
OWNER SPECIAL:
Can be rented with Main House listing 31591.
Summer:
$450 - $900/night
$3,275 - $3,975/wk
$8,000 - $18,000/mo
Off Season:
$400 - $850/night
$2,475 - $3,275/wk
$5,000 - $30,000/mo
Oak Bluffs
ID 42078
- 1 BR
- 2 baths
- Sleeps 4
Design-led modern cottage in the heart of Oak Bluffs
Distance to beach: 1.5 miles to Inkwell Beach Oak Bluffs Town Beach
Summer:
$6,075 - $6,575/wk
Off Season:
$2,575 - $5,575/wk
Oak Bluffs vacation rentals that sleep 3
Oak Bluffs
ID 36402
- 1 BR
- 1 bath
- Sleeps 3
Renovated Cozy Seaside Cottage with Views of Town Beach
Distance to beach: 200 feet to Oak Bluffs Town Beach
Summer:
$3,000 - $3,500/wk
Off Season:
$2,700 - $3,000/wk
$2,000/mo
Oak Bluffs Arts District
ID 42077
- 1 BR
- 1 bath
- Sleeps 3
The Loft at Ginsey
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
5.01 review
OWNER SPECIAL:
New Listing In Primary OB location! Weekly or Winter Rental Available.
Summer:
$2,000 - $2,200/wk
Off Season:
$1,200 - $1,800/wk
$3,000/mo
5
Oak Bluffs
ID 39489
- 1 BR
- 1 bath
- Sleeps 3
The Purple Door Garden Suite Lower Level Heart of Oak Bluffs
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
4.47 reviews
Summer:
$450 - $550/night
$2,500 - $3,200/wk
Off Season:
$250 - $500/night
$1,000 - $2,500/wk
$1,000 - $5,000/mo
6
Oak Bluffs vacation rentals that sleep 2
Oak Bluffs
ID 11609
- 1 BR
- 2 baths
- Sleeps 2
Sweet Pea Cottage, Walk To Beach
Distance to beach: 1/10 mile Oak Bluffs Town Beach
69 reviews
Summer:
$2,050 - $2,700/wk
Off Season:
$350 - $450/night
$1,750 - $2,100/wk
Oak Bluffs
ID 32208
- 1 BR
- 1 bath
- Sleeps 2
''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
5.09 reviews
OWNER SPECIAL:
flexible dates in shoulder seasons!
Summer:
$3,025 - $5,425/wk
$9,500 - $25,000/mo
Off Season:
$400 - $800/night
$2,225 - $4,725/wk
$6,000 - $16,000/mo
2
Oak Bluffs
ID 34909
- 1 BR
- 1 bath
- Sleeps 2
CozyBluffs - Walk to Beach/Circuit Ave/OB ferries!
Distance to beach: 1/2 mi to The Jetty Beach
8 reviews
OWNER SPECIAL:
Enjoy the ease of Fall in Oak Bluffs & get 20% off remaining 2026 dates! (3 night min).
Summer:
$4,838 - $5,538/wk
Off Season:
$399 - $749/night
$3,088 - $5,538/wk
$3,500 - $4,500/mo
6
Oak Bluffs
ID 40032
- 1 BR
- 1 bath
- Sleeps 2
Tiny House.... BIG Vacation opportunity
Distance to beach: 1.4 mi to Oak Bluffs Town Beach and 1/2 mi to Eastville Beach
Off Season:
$200 - $300/night
$2,500/wk
2
Oak Bluffs
ID 41194
- 1 BR
- 1 bath
- Sleeps 2
Charming and Centrally Located Garage Apartment
Distance to beach: 3.5 mi to Oak Bluffs Town Beach and 3.5 South Beach - Katama
Off Season:
$2,200/wk