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Oak Bluffs Rentals

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From $3732 per night (USD)
VRBO
Cozy 4-bedroom condo in perfect Oak Bluffs with AC, on Circuit Ave, WiFi!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Escape to this delightful Oak Bluffs condo, perfectly located for enjoying all that town has to offer. With four comfort ...
From $3732 per night (USD)
VRBO
From $1858 per night (USD)
VRBO
Condo facing Kennebec with AC in charming Oak Bluffs, WiFi, TV, 2 Queen beds
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a peaceful stay at this condo in Oak Bluffs, there is one bedroom, with Queen bed, on the top floor with an outdoo ...
From $1858 per night (USD)
VRBO
From $3155 per night (USD)
VRBO
5-Bedroom Waterfront Retreat on Seaview Ave in Oak Bluffs
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Part of the exquisite waterfront retreat that is 348 Seaview Avenue in Oak Bluffs is the thoughtfully renovated 5-bedroo ...
From $3155 per night (USD)
VRBO
From $2426 per night (USD)
VRBO
Spacious 6-bedroom house in fantastic Oak Bluffs with AC
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Welcome to this beautiful house in Oak Bluffs. With six bedrooms, including five queen beds, a twin bed, and a bunk bed, ...
From $2426 per night (USD)
VRBO
From $1038 per night (USD)
VRBO
Aunt Clara's Cottage ~ Your Beautiful Island Home!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Your island time starts here. Set on New York Avenue in the heart of Oak Bluffs, Aunt Clara’s Cottage puts you steps fro ...
From $1038 per night (USD)
VRBO
From $1081 per night (USD)
VRBO
Newly renovated home in Oak Bluffs. Walk to private beach on the Lagoon.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated home in Oak Bluffs, conveniently located between downtown Oak Bluffs and Vineyard Haven. Enjoy an ...
From $1081 per night (USD)
VRBO
From $1033 per night (USD)
VRBO
East Chop Escape - Water Views, Roof Deck & Minutes to Oak Bluffs
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the charm of Martha's Vineyard from this beautifully light-filled tri-level home in the highly desirable East ...
From $1033 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Waterfront Retreat w/ Guest Cottage & Sunsets
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Experience the beauty of Martha’s Vineyard from this private waterfront retreat overlooking the Lagoon in Oak Bluffs. Ne ...
From $366 per night (USD)
VRBO
From $1207 per night (USD)
VRBO
The Cottage - Part of a waterfront compound in Oak Bluffs, Martha's Vineyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Cottage, a well-appointed 2-bedroom home that is part of the waterfront compound that makes up 348 Sea Vi ...
From $1207 per night (USD)
VRBO
From $1892 per night (USD)
VRBO
Historic 6BR—Walk to Beach & Circuit Ave
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Stay in a spacious six-bedroom historic Colonial within walking distance of Circuit Avenue, Oak Bluffs Harbor and the be ...
From $1892 per night (USD)
VRBO
From $510 per night (USD)
VRBO
Cozy Cottage in Oak Bluffs - Close to town and beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Rustic, Walk-to-Town Cottage in the Heart of Oak Bluffs Set on a peaceful road just steps from the center of Oak Bluffs, ...
From $510 per night (USD)
VRBO
From $631 per night (USD)
VRBO
Charming Martha's Vineyard Cottage Minutes from the Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Our family’s Oak Bluffs home on County Road is set up for easy summer living on Martha’s Vineyard. Sleeps up to 8 with a ...
From $631 per night (USD)
VRBO
From $817 per night (USD)
VRBO
Serene 3-bedroom condo in charming Martha's Vineyard Oak Bluffs.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has bee ...
From $817 per night (USD)
VRBO
From $1010 per night (USD)
VRBO
Perfect Vineyard escape steps away from Lagoon Pond and Oak Bluffs
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this beautifully updated 3-bedroom home, just 500 feet from Lagoon Pond—perfect for swimming, kayaking, and pa ...
From $1010 per night (USD)
VRBO
From $995 per night (USD)
VRBO
Beautiful 5BR Oak Bluffs Home with AC - Walk to Beaches, Town & Ferry
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Enjoy the best of Oak Bluffs from this spacious 5-bedroom, 4.5-bath Martha’s Vineyard home. Located near downtown Oak Bl ...
From $995 per night (USD)
VRBO
From $948 per night (USD)
VRBO
Gorgeous home in Oak Bluffs
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Have the perfect vineyard getaway at this beautiful home in Oak Bluffs. Only a 10 minute walk from the Oak Bluffs ferry ...
From $948 per night (USD)
VRBO
From $820 per night (USD)
VRBO
Oak Bluffs Home Walk to Town, Beaches & Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
give me a less than 80 character headline for this description: Welcome to 22 Wing Road in Oak Bluffs, a newly renovate ...
From $820 per night (USD)
VRBO
From $937 per night (USD)
VRBO
Walk to Beach in Oak Bluffs - Private First Floor Retreat w/ Deck & Fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect Martha's Vineyard getaway! This beautifully designed first-floor retreat offers comfort, space, ...
From $937 per night (USD)
VRBO
From $532 per night (USD)
VRBO
3rd Floor apt w/kitchenette + W/D & Private Entry + Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Escape to the third floor of this spacious Oak Bluffs home, offering a private and comfortable retreat just a short walk ...
From $532 per night (USD)
VRBO
From $570 per night (USD)
VRBO
Third Floor 3BR Chimney Suite + Deck Access + Walk to Beach +Washer/Dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Perched on the third floor, the Chimney Suite offers a private and spacious retreat just a short walk from the beach. Th ...
From $570 per night (USD)
VRBO
From $2539 per night (USD)
VRBO
Fully Renovated Oak Bluffs Designer Retreat
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Oak Bluffs Allure is a fully renovated custom home that features a 3-bedroom, 3.5-bath main house and a detached 1-bedro ...
From $2539 per night (USD)
VRBO
From $1577 per night (USD)
VRBO
4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Located in a very quiet Oak Bluffs neighborhood, two miles from the Atlantic Ocean and Town Center. Get ready for a vaca ...
From $1577 per night (USD)
VRBO
From $596 per night (USD)
VRBO
Brick Ranch On Cul-de-Sac with Central Air/Heat In Quiet Neighborhood Oak Bluffs
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This lovely house features 3 inviting bedrooms, Two each with queen beds and third bedroom with 2 twin beds and an upsta ...
From $596 per night (USD)
VRBO
From $945 per night (USD)
VRBO
Oak Bluffs close to Town & Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Tucked away on a quiet cul-de-sac, this bright and spacious Oak Bluffs home is just minutes from town. With an open floo ...
From $945 per night (USD)
VRBO
From $2953 per night (USD)
VRBO
Heated pool & hot tub with pond views in Farm Neck
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
Up-island views and privacy with down-island convenience! Enjoy a relaxing stay in a charming, secluded, five-bedroom, ...
From $2953 per night (USD)
VRBO
From $1112 per night (USD)
VRBO
East Chop Home - Walk to Town & Beach, WiFi/AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience Martha's Vineyard from this beautifully renovated 2024 gem in sought-after East Chop. Just a short stroll to ...
From $1112 per night (USD)
VRBO
From $875 per night (USD)
VRBO
0.8 miles to Circuit Avenue in Downtown Oak Bluffs
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Charming and comfortable 3-bedroom home in the heart of Oak Bluffs, perfect for a relaxing Vineyard escape. The home fea ...
From $875 per night (USD)
VRBO
From $848 per night (USD)
VRBO
Charming 3-bedroom cottage in Oak Bluffs with AC, WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Escape to this renovated 3-bedroom home in Oak Bluffs, across from Farm Neck Golf Club. The Beach is just a 4-minute dri ...
From $848 per night (USD)
VRBO
From $4442 per night (USD)
VRBO
Beautiful Estate with salt water pool & pond with kayaks
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without any per ...
From $4442 per night (USD)
VRBO
From $1841 per night (USD)
VRBO
Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Six bedroom, five and a half bath contemporary island home located in Waterview Farm with direct access to the beach on ...
From $1841 per night (USD)
VRBO
From $1196 per night (USD)
VRBO
PRIVATE WATER ACCESS! ON FARM NECK GOLF COURSE! Kayaks & Canoe & A/C
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Immaculately clean, beautifully furnished three bedroom, 2 and 1/2 bath beach house in private community. Community is ...
From $1196 per night (USD)
VRBO
From $608 per night (USD)
VRBO
Effortless access to OB-ET-VH. Grilled lobster & ocean breezes are calling you!
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
(DM me before booking!) Tucked away on 1.5 acres of wooded privacy, Ellen’s Hideaway is a beautifully renovated, sun‑fi ...
From $608 per night (USD)
VRBO
From $579 per night (USD)
VRBO
Beautiful home with pool in great location- close to everything!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom home with 2 big full bathrooms. Walk to ferry and town center. One of the bathrooms include a jacuzzi tub and ...
From $579 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Welcome to the Oak Bluffs Victorian Cottage that dreams are made of! Newly renovated (summer 2017), the rambling Main H ...
Click For Pricing
Expedia
From $1060 per night (USD)
VRBO
BRAND NEW!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Beautiful, brand new 5 BR, 2.5 BA w/ outdoor shower Cape-Style Home on 1 Acre of land minutes away from downtown Oak Blu ...
From $1060 per night (USD)
VRBO
From $925 per night (USD)
VRBO
Private Oak Bluffs Retreat w/AC • Fire Pit • Outdoor Living
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Central AC • Private landscaped setting • Huge deck & bluestone patio • Lynx professional grill • Fire pit • Outdoor sho ...
From $925 per night (USD)
VRBO
From $1454 per night (USD)
VRBO
Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Nestled on a quiet road within walking distance to Oak Bluffs, this 3-bedroom house with a separate 1-bedroom guest hou ...
From $1454 per night (USD)
VRBO
From $578 per night (USD)
VRBO
The Sweetest Suite – Beach, kayaks & Starry Nights
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your perfect island escape. Tucked beneath a canopy of soaring 70-foot trees, our charming guest suite offers ...
From $578 per night (USD)
VRBO
From $424 per night (USD)
VRBO
The Nest, Comfortable, Cozy and Convenient
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Nest is a private entranced guesthouse that is ideally located 2/3-1 mile walking distance to Oak Bluffs town, har ...
From $424 per night (USD)
VRBO
From $2008 per night (USD)
VRBO
Spectacular Classic Waterfront Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
33 Beach captures the essence of Martha's Vineyard. Built around the turn of the century as a stop for the New York Yach ...
From $2008 per night (USD)
VRBO
From $1092 per night (USD)
VRBO
The Island Collection MV: Experience a Luxury Getaway by the Lagoon
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you ...
From $1092 per night (USD)
VRBO
From $1587 per night (USD)
VRBO
Oceanfront Home - Walk to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Please note that during the summer (June/July/August) we are a SATURDAY to SATURDAY rental. We are not accepting booki ...
From $1587 per night (USD)
VRBO
From $712 per night (USD)
VRBO
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away ...
From $712 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Downtown Oak Bluffs, short walk to beach & town; NOW AVAIL - 7/25-8/1. DISCOUNT!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Location, location, location. This cozy 3 bedroom house is located steps from downtown on a family neighborhood side str ...
From $454 per night (USD)
VRBO
From $654 per night (USD)
VRBO
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in the desirable, private Meadow View Farms Estates, across from the Farm Neck Golf Club, this charmingly decora ...
From $654 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Serene Sengekontacket Pond Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The property is set among several private townhouses in a lovely neighborhood located off of Sengekontacket Pond in Oa ...
From $552 per night (USD)
Expedia
From $765 per night (USD)
VRBO
Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Located on historic Circuit Ave in Oak Bluffs within walking distance to town, beach, tennis courts and parks. Minutes a ...
From $765 per night (USD)
VRBO
From $992 per night (USD)
VRBO
Adorable Oak Bluffs Cottage With Ac On East Chop
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Adorable 4 bedroom cottage in the East Chop neighborhood of Oak Bluffs. You will love the beautiful back yard that has a ...
From $992 per night (USD)
VRBO
From $890 per night (USD)
VRBO
Beach, Town, Tennis, Pickleball - Central AC
Bedrooms:
2
Bathrooms:
6
Sleeps:
15
We will let the photos do the talking, but note that this home has some especially attractive features for large groups, ...
From $890 per night (USD)
VRBO
$Your \Vineyard Dream\ Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town$
From $606 per night (USD)
VRBO
Your \"Vineyard Dream\" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A BEAUTIFUL PROPERTY CLOSE TO TOWN-GREAT PRICE! LOTS OF PRIVACY BUT CLOSE TO EVERYTHING IN OB. ONE WEEK MINIMUM FOR ALL ...
From $606 per night (USD)
VRBO
From $1515 per night (USD)
VRBO
Cape Style Home in Oak Bluffs, Walk to Town, 4 Bedrooms/3 Full Baths A/C
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to your Oak Bluffs getaway, where classic Cape Cod charm meets relaxed Vineyard living. This beautifully appoint ...
From $1515 per night (USD)
VRBO
From $1407 per night (USD)
VRBO
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Retreat to Martha's Vineyard in a modern ranch style vacation home with a heated pool tucked on 1.5 acres of landscaped ...
From $1407 per night (USD)
VRBO
From $625 per night (USD)
VRBO
4 bedroom home family friendly in desirable area
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This 4 bedroom, 3-story home has plenty of space to relax with two decks and a private third level master suite. Located ...
From $625 per night (USD)
VRBO
From $2049 per night (USD)
VRBO
The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views!
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away ...
From $2049 per night (USD)
VRBO
Click For Pricing
VRBO
Charming Studio Guest House in the Heart of Oak Bluffs
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This recently renovated charming studio guest house in the heart of Oak Bluffs sleeps 2 in a Queen size bed. Complete w ...
Click For Pricing
VRBO
From $474 per night (USD)
VRBO
Sweet Little Post&Beam
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Very comfortable well appointed 750 sq ft home with heat and AC. Has 1 bedroom upstairs with a queen size bed and a hal ...
From $474 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Extra-large gingerbread cottage in historic Campgrounds in Oak Bluffs, sleeps nine. Located on a double lot in the hear ...
From $710 per night (USD)
VRBO
From $978 per night (USD)
VRBO
Last week of August now available!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This is one summer school you won't want to miss! Bright, airy, elegant home is perfect combination of past and present ...
From $978 per night (USD)
VRBO
Click For Pricing
VRBO
ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Gorgeous newly renovated and newly furnished mid-century beach cottage designed by prominent interior design firm Tersig ...
Click For Pricing
VRBO
From $744 per night (USD)
VRBO
Island Serenity: Beautiful home in quiet neighborhood close to Oak Bluffs
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely 3 bedroom, 2 full bathroom home with huge deck is less than 1 mile walk to famous Circuit Avenue in Oak Bluffs an ...
From $744 per night (USD)
VRBO
From $504 per night (USD)
VRBO
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car prkng
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Lovely private first floor of raised ranch house. Sleeps Four in 2 bedrooms (queen and two singles). One and a half bat ...
From $504 per night (USD)
VRBO
From $1362 per night (USD)
VRBO
OAK BLUFFS - INKWELL WATERVIEW Renovated Cottage with A/C, modern decor
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautifully renovated in-town Victorian Cottage. 4 bedrooms and 2.5 baths. 2 of the 4 bedrooms with a partial water view ...
From $1362 per night (USD)
VRBO
From $1515 per night (USD)
VRBO
East Chop Beach House w/Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Fabulous new house in East Chop completed in 2019 located in the heart of East Chop. The house is well appointed, very ...
From $1515 per night (USD)
VRBO
From $386 per night (USD)
VRBO
Arrowsmith Cottage - Oak Bluffs Near Eastville Beach; Steps to bike path.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Please note - If you are considering bringing your pet, one small dog may be considered, but we ask that you send an ini ...
From $386 per night (USD)
VRBO
From $1467 per night (USD)
VRBO
Original Pratt House built in 1866 with Ocean View of the Inkwell beach.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was ...
From $1467 per night (USD)
VRBO
From $331 per night (USD)
VRBO
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Tucked in a quiet neighborhood and within walking distance to town and beaches, this quaint cottage was moved to East Ch ...
From $331 per night (USD)
VRBO
From $430 per night (USD)
VRBO
Conveniently located near Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This comfortable home has all the amenities of home in an idyllic setting, easy access to town, beach and gorgeous East ...
From $430 per night (USD)
VRBO
Click For Pricing
VRBO
Best Kept Secret Retreat for Adults with Water & Golf Course Views!
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Quite, serene, tranquil & beautiful are words guests have used to describe this home. This newly renovated home provide ...
Click For Pricing
VRBO
From $631 per night (USD)
VRBO
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Mid-century rustic cottage charm tucked on 3 acres 1 mi to Oak Bluffs and Vineyard Haven center's. Acquired in 1950 by L ...
From $631 per night (USD)
VRBO
From $848 per night (USD)
VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! Deck,A/C,Outdoor Shower, Wifi
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $848 per night (USD)
VRBO
From $561 per night (USD)
VRBO
Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This comfortable house provides up and downstairs amenities. The master bedroom with bath is on the ground floor; the o ...
From $561 per night (USD)
VRBO
From $798 per night (USD)
VRBO
In-Town Certified National Historic Oak Bluffs Property -
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the ...
From $798 per night (USD)
VRBO
From $972 per night (USD)
VRBO
Oak Bluffs Cottage - A Short Walk to the Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stay in this beautiful Vineyard home and enjoy a relaxing vacation back in time! Within 5 minutes of stepping out the f ...
From $972 per night (USD)
VRBO
From $693 per night (USD)
Expedia
Water View 1 mi from Oak Bluffs 10 min Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked ...
From $693 per night (USD)
Expedia
From $1722 per night (USD)
VRBO
Waterfront Home in Oak Bluffs - Walk to Town and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This lovely four-bedroom shingled Cape overlooks Farm Pond, Harthaven, and Nantucket Sound. It is a vintage cottage com ...
From $1722 per night (USD)
VRBO
From $1572 per night (USD)
Expedia
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Pirate's Reef is a NEW and beautifully decorated residence that offers 5 spacious bedrooms (2 master suites!) with 4.5 b ...
From $1572 per night (USD)
Expedia
From $2128 per night (USD)
VRBO
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
GAME ROOM!!! We have converted the room in the garage as a place where our guests can go should you have a rainy day or ...
From $2128 per night (USD)
VRBO
From $1204 per night (USD)
VRBO
Completely renovated, air conditioned cottage close to the beach. Dog friendly.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property has something for the whole family to enjoy. A large wrap-around porch, screened in dining area on side po ...
From $1204 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Location, Charm, & Steps to Town/Beach -- Central AC, 100% Renewable Energy
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
(Note: for 2025, we are renovating the upstairs bath and creating a more spa-like shower. New Photos by late March, rou ...
From $538 per night (USD)
VRBO
From $3585 per night (USD)
VRBO
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
6 Bedrooms, Sleeping Porch, 3 Full Baths, 2 Half Baths, Sleeps 12+ A timeless Martha’s Vineyard escape awaits you at th ...
From $3585 per night (USD)
VRBO
From $1385 per night (USD)
VRBO
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy everything the island has to offer in a spacious, custom-built, fully-stocked modern farmhouse and backyard oasis ...
From $1385 per night (USD)
VRBO
From $668 per night (USD)
VRBO
Close to town, beautifully updated
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Renovated Oak Bluffs home features 4 bedrooms and 2 full Baths. The house is located in a quiet neighborhood and one mil ...
From $668 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Comfortable Island Home, Easy Access to Beaches and Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down ...
From $493 per night (USD)
VRBO
From $1254 per night (USD)
VRBO
Multiple Ensuites, Central Air, Perfect Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Spacious ~2,200 sq. ft. home featuring 4 bedrooms and 3.5 bathrooms. Three bedrooms on the second floor include en-suite ...
From $1254 per night (USD)
VRBO
From $1476 per night (USD)
VRBO
Gingerbread cottage with stunning Oak Bluffs Harbor View
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Amazing vacation spot Enjoy beautiful views of Oak Bluffs Harbor and beyond Historic gingerbread cottage Large front por ...
From $1476 per night (USD)
VRBO
From $1068 per night (USD)
VRBO
Location, Location, Location- Updated East Chop Year Round Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oak Bluffs: Located in East Chop! Beautiful year round home steps to Oak Bluffs Harbor, East Chop Beach Club, Jetty Beac ...
From $1068 per night (USD)
VRBO
From $594 per night (USD)
VRBO
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Small beachfront cottage; back deck is right on the water and the front door is on Beach Rd. where you can flag down a b ...
From $594 per night (USD)
VRBO
From $863 per night (USD)
VRBO
Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come experience the magic of the Vineyard in our island home. This charming residence is clean, cozy and boasts modern f ...
From $863 per night (USD)
VRBO
From $712 per night (USD)
VRBO
Beautiful Contemporary Farmhouse close to Oak Bluffs
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
WEEK OF JUNE 27th TO JULY 4th AVAILABLE. HAVE TRANSFERABLE FERRY TICKETS AVAILABLE FOR PURCHASE. Beautifully maintaine ...
From $712 per night (USD)
VRBO
From $651 per night (USD)
VRBO
Martha's Vineyard Beachfront Condo in Oak Bluffs
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy all that Martha's Vineyard has to offer in this spacious two bedroom, two full bath beautifully furnished condo ov ...
From $651 per night (USD)
VRBO
From $1121 per night (USD)
VRBO
Secluded Escape- Central AC & Wireless Internet Access.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 270 ...
From $1121 per night (USD)
VRBO
From $819 per night (USD)
VRBO
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Prime location close to the center of town in the fabulous SeaView Condo building in the heart of Oak Bluffs. Highly des ...
From $819 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Oak Bluffs - Quiet neighborhood
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Less than a mile from downtown, harbor and beach. Located in a quiet neighborhood, guests are sure to enjoy a memorable ...
From $545 per night (USD)
VRBO
From $3704 per night (USD)
VRBO
Maison Calme/Peaceful Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This luxury enclave, complete with 4 bedrooms and 3.5 bathrooms, is located in a private community that is centrally loc ...
From $3704 per night (USD)
VRBO
From $686 per night (USD)
VRBO
A BRILLANT WAY Central Location To Beach/Shops/Restaurants/Arcade/Family Bowling
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A Brillant Way is a Brilliant Condo located in the heart of Oak Bluffs. Second level has 2 bedrooms - Queen size bed in ...
From $686 per night (USD)
VRBO
From $571 per night (USD)
VRBO
Oak Bluffs Cutie Near Beach + Town Center! Ferry tix available for some dates!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy both worlds - a peaceful atmosphere with many comfortable places to escape to read, nap or chat, near the heart of ...
From $571 per night (USD)
VRBO
From $904 per night (USD)
VRBO
Oak Bluffs Gingerbread Cottage near Downtown, Beach, Ferry and Ocean Park!
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
- Magnificent front porch for rocking and peaceful island observations! - All furniture is whimsical and light to match ...
From $904 per night (USD)
VRBO
From $688 per night (USD)
VRBO
Perfect Home For A Family Vacation With All The Amenities
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
This professionally designed & decorated vacation home is great for a quiet get away for one or two couples/families or ...
From $688 per night (USD)
VRBO
From $785 per night (USD)
VRBO
Spacious family house, short walk to the Lagoon & close to Oak Bluffs center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The 'Anchor Inn' on Carole Avenue is the perfect spot for your family to relax and enjoy the Vineyard! The home is a 4 ...
From $785 per night (USD)
VRBO
From $909 per night (USD)
VRBO
OB Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Best of everything: We are located on the back side of Farm Pond, which overlooks Harthaven, Nantucket Sound, and Chappa ...
From $909 per night (USD)
VRBO

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Results: 293 Rentals