Sumner Park Rentals
From $801 per night (USD)VRBO
Elegant Dream Home w\/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Oak Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $801 per night (USD)VRBO
From $794 per night (USD)Expedia
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to "Eventide." Your historic vacation home is nestled at 63 Temahigan Ave. in Oak Bluffs- Martha's Vineyard. Con ...
From $794 per night (USD)Expedia
From $866 per night (USD)VRBO
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Renovated in 2022, The Panola House is tucked away on a private lot with its own roundabout driveway. Walk to the cente ...
From $866 per night (USD)VRBO
From $309 per night (USD)Expedia
Historic Oak Bluffs home, short walk to town, beach, and harbor.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about ...
From $309 per night (USD)Expedia
From $499 per night (USD)VRBO
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w\/AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Best of both worlds! Quietly situated among beautiful trees with few neighbors plus it is walking distance to swim and O ...
From $499 per night (USD)VRBO
From $732 per night (USD)Expedia
Historic Home with Gorgeous Antiques & Mondern Conveniences
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Samoset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $732 per night (USD)Expedia
From $732 per night (USD)VRBO
Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bright Grove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $732 per night (USD)VRBO
From $761 per night (USD)Expedia
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation ...
From $761 per night (USD)Expedia
From $489 per night (USD)VRBO
Cozy cottage 3\/4 mile from Oak Bluffs harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Family owned/charming home in Oak Bluffs, 1/2 mile walk to East Chop Lighthouse and slightly more to the town harbor, wh ...
From $489 per night (USD)VRBO
From $519 per night (USD)Expedia
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset Meadows Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $519 per night (USD)Expedia
From $609 per night (USD)VRBO
Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the charm of Martha’s Vineyard at your leisure from this ideally located apartment. With 2 bedrooms and 1 bat ...
From $609 per night (USD)VRBO
From $479 per night (USD)Expedia
Quaint,,,Quiet..up island feel yet a short walk to town and harbor
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Your quintessential summer vacation starts here! The property has a combination of a strong rental history(read ren ...
From $479 per night (USD)Expedia
From $799 per night (USD)VRBO
Beautiful downtown Oak Bluffs!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully decorated ranch style home in Oak Bluffs Center. Close to the beach, restaurants, shopping, parks, library a ...
From $799 per night (USD)VRBO
From $825 per night (USD)Expedia
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect Chuck Sullivan and buil ...
From $825 per night (USD)Expedia
From $635 per night (USD)VRBO
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Oak Leaf Cape Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $635 per night (USD)VRBO
From $1202 per night (USD)Expedia
Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 8
Classic Oak Bluffs Beach Home- Excellent Harbor Views- Near Shops & Dining Our calendar is updated in real-time & our n ...
From $1202 per night (USD)Expedia
From $441 per night (USD)VRBO
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $441 per night (USD)VRBO
From $1400 per night (USD)Expedia
Beautiful 5 BR, 4.5 baths w\/ modern conveniences
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
We welcome you to enjoy our spacious and comfortable home. It's a beautiful 5 BR, 4.5 bath Oak Bluffs home with modern ...
From $1400 per night (USD)Expedia
From $722 per night (USD)VRBO
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity, ...
From $722 per night (USD)VRBO
From $722 per night (USD)Expedia
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity ...
From $722 per night (USD)Expedia
From $560 per night (USD)VRBO
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
There's no better way to experience the laidback lifestyle of the Vineyard than in the heart of it all at this tradition ...
From $560 per night (USD)VRBO
From $581 per night (USD)Expedia
Peaceful Oak Bluffs home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax and pamper yourself kin a Mid-Century Modern Split-Level home. Located on a 1/4 acre lot minutes away from town,b ...
From $581 per night (USD)Expedia
From $1155 per night (USD)VRBO
New Construction with Patio & Yard - Downtown & Beaches
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Oak Bluffs Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1155 per night (USD)VRBO
From $540 per night (USD)Expedia
Bright old-world cottage with two porches & large yard - walk to town & beaches
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Oak Bluffs Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $540 per night (USD)Expedia
From $1076 per night (USD)VRBO
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w\/AC
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 10
The cottage is in restored original condition with many original features including hardwood floors, paned windows with ...
From $1076 per night (USD)VRBO
From $450 per night (USD)Expedia
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Winthrop Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $450 per night (USD)Expedia
From $838 per night (USD)VRBO
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely, spacious, and beautifully appointed condo is just steps from the beach and a short walk to the heart of Oak ...
From $838 per night (USD)VRBO
From $973 per night (USD)Expedia
Oak Bluffs - Quiet Neighborhood - Walk to Town, Ferry, Library and more!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is situated in a quiet neighborhood just a short walk to downtown Oak Bluffs. This location is perfect. ...
From $973 per night (USD)Expedia
From $391 per night (USD)VRBO
Cozy Beach Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Newly refurbished Cottage City Victorian beach house, built in 1870. Walk to beach, walk to town. 2 bedrooms up a narro ...
From $391 per night (USD)VRBO
From $1729 per night (USD)Expedia
Akwaaba House Martha's Vineyard Walk to Beach and Oak Bluffs Town & Harbor
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Newly renovated, Great for Family & Friend Stays, Corporate Retreats, Central Air & Heat, walk to Circuit Ave and Beach, ...
From $1729 per night (USD)Expedia
From $751 per night (USD)VRBO
Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
*** CONTACT THE HOST TO CONFIRM DATES BEFORE INSTANT BOOKING. VRBO FEES ARE NON-REFUNDABLE *** *** CONTACT THE HOST FOR ...
From $751 per night (USD)VRBO
From $481 per night (USD)Expedia
Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Vineyard Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $481 per night (USD)Expedia
From $689 per night (USD)VRBO
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
This home has all the amenities to make your stay a comfortable one. Its character stems from being built in the 1920s w ...
From $689 per night (USD)VRBO
From $987 per night (USD)Expedia
Beautiful Carriage House on the Chop
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Recently built, this spectacular 3 Bedroom carriage house is located on 3/4 acre estate on beautiful East Chop Drive. Th ...
From $987 per night (USD)Expedia
From $460 per night (USD)VRBO
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Brewster House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $460 per night (USD)VRBO
From $1304 per night (USD)Expedia
Newly remodeled home w\/ new furniture, large yard & great porches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunny Side Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1304 per night (USD)Expedia
Click For PricingVRBO
Traditional Martha's Vineyard Home w\/ Porch & Yard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This exquisite, shingled Colonial house with an expansive wraparound porch is synonymous with Martha's Vineyard architec ...
Click For PricingVRBO
Click For PricingExpedia
Quaint and pristine home with private suites and baths.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our home! We are a husband & wife interior decorator/contractor team, who've tastefully renovated our entire ...
Click For PricingExpedia
From $909 per night (USD)VRBO
Welcome to \"Suzy's Place\" Best Location! Walk Everywhere. Newly built in 2024.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
"Suzy's Place" is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful new ...
From $909 per night (USD)VRBO
From $1105 per night (USD)Expedia
Updated house close to town and beach with patio, AC, and games
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Sankofa House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1105 per night (USD)Expedia
From $911 per night (USD)VRBO
Oak Bluffs Spacious 4-Bedroom Rental – Private Entrance & Newly Renovated Deck!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious 4-Bedroom Rental in Oak Bluffs – Private Entrance & Newly Renovated Deck! Enjoy the best of Oak Bluffs in this ...
From $911 per night (USD)VRBO
From $967 per night (USD)Expedia
Steps to Inkwell Beach: Victorian Home!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
2,150 Sq Ft | Family Friendly | Walk to Shops, Restaurants, Ferry Terminal | Outdoor Shower & Grill It doesn't get any ...
From $967 per night (USD)Expedia
From $472 per night (USD)VRBO
NEWLY RENOVATED! Quiet location, walk to Circuit Avenue and beaches!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Your home away from home in Oak Bluffs with 4 bedrooms, including a ground floor bedroom and bath with zero-entry shower ...
From $472 per night (USD)VRBO
From $458 per night (USD)Expedia
BRAND NEW 1-bedroom Owner's Suite in wonderful Oak Bluffs with Air Conditioning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this 1-bedroom Owner's Suite in Oak Bluffs. This brand new property features a cozy bedroom with a ...
From $458 per night (USD)Expedia
From $1254 per night (USD)VRBO
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Come stay at our quaint Victorian cottage overlooking downtown Oak Bluffs and the Harbor, which are just a few blocks aw ...
From $1254 per night (USD)VRBO
From $1078 per night (USD)Expedia
Designer Stay- Large Yard- Outdoor games
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just ...
From $1078 per night (USD)Expedia
From $443 per night (USD)VRBO
Updated 3-bedroom in gorgeous Oak Bluffs w\/ waterviews and expansive front porch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom cottage in Oak Bluffs. Nestled in a peaceful neighborhood, this beautiful property ...
From $443 per night (USD)VRBO
From $465 per night (USD)Expedia
Martha’s Vineyard 15 minute walk to Oak Bluffs Beach and Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
15 minute walk to Oak Bluffs town and beach. 2 queen beds. 5 minute walk to the bus. 5 minute walk to library. 1 bedroom ...
From $465 per night (USD)Expedia
From $1617 per night (USD)VRBO
Cozy Oak Bluffs Cottage walk to town Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This modest single-family home was newly renovated in 2023. It is a single-level house just west of downtown Oak Bluffs. ...
From $1617 per night (USD)VRBO
From $862 per night (USD)Expedia
4 BR\/4 BA Modern Victorian: The Mack on Winemack
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful Victorian home has all the charm of a true Martha’s Vineyard Gingerbread cottage combined with all of the ...
From $862 per night (USD)Expedia
From $1383 per night (USD)VRBO
OAK BLUFFS - INKWELL WATERVIEW Renovated Cottage with A\/C, modern decor
- Bedrooms:
- 3
- 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 $1383 per night (USD)VRBO
From $796 per night (USD)Expedia
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
- Bedrooms:
- 3
- 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 $796 per night (USD)Expedia
From $1056 per night (USD)VRBO
Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom\/3 Bath A\/C
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This newly renovated home is approximately 2100sf with 4 bedrooms and 3 bathrooms. Furnished and decorated by award winn ...
From $1056 per night (USD)VRBO
From $541 per night (USD)Expedia
Downtown Oak Bluffs, short walk to beach & town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Location, location, location. This cozy 3 bedroom house is located steps from downtown on a family neighborhood side str ...
From $541 per night (USD)Expedia
From $959 per night (USD)VRBO
Spacious Home - 1500 ft from Beach & Circuit Ave
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated four bedroom, two full bathroom home with an inviting front porch, private backyard and footsteps to Ci ...
From $959 per night (USD)VRBO
From $626 per night (USD)Expedia
Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Located on historic Circuit Ave in Oak Bluffs within walking distance to town, beach, tennis courts and parks. Minutes a ...
From $626 per night (USD)Expedia
From $392 per night (USD)VRBO
Great location, happy house 0.5 mile Nancy’s & Jetty Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
1900's Victorian, renovated and newly furnished. House is located on New York Ave, which is the main road between Oak Bl ...
From $392 per night (USD)VRBO
From $545 per night (USD)Expedia
Adorable Oak Bluffs Cottage With Ac On East Chop
- Bedrooms:
- 3
- 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 $545 per night (USD)Expedia
From $1005 per night (USD)VRBO
Beach, Town, and Tennis - Central AC
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 15
We will let the photos do the talking, but note that this home has some especially attractive features for large groups, ...
From $1005 per night (USD)VRBO
From $475 per night (USD)Expedia
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 $475 per night (USD)Expedia
From $987 per night (USD)VRBO
PRIVATE WATER ACCESS! ON FARM NECK GOLF COURSE! Kayaks & Canoe & A\/C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Immaculately clean, beautifully furnished three bedroom, 2 and 1/2 bath beach house in private community. Community is ...
From $987 per night (USD)VRBO
From $847 per night (USD)Expedia
Magnificent Spacious Home
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
This lovely and beautifully furnished three-story home is located in a quiet residential section of Oak Bluffs. It is a ...
From $847 per night (USD)Expedia
From $437 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 $437 per night (USD)VRBO
From $784 per night (USD)Expedia
Beach and downtown OB walkable! 5 Bedroom Victorian on the park.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
You will find this 5 Bedroom Victorian quite charming with its bright & cheery interior. Located right across from wide ...
From $784 per night (USD)Expedia
From $1908 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 $1908 per night (USD)VRBO
From $709 per night (USD)Expedia
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 $709 per night (USD)Expedia
From $995 per night (USD)VRBO
Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to the Oak Bluffs Victorian Cottage that dreams are made of! Newly renovated (summer 2017), the rambling Main H ...
From $995 per night (USD)VRBO
From $1186 per night (USD)Expedia
Coastal Farmhouse With Connected Carriage House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
**SUMMER SPECIAL: SAVE $1,000/WEEK OFF ALL OPEN JUNE, JULY + AUGUST WEEKS | NEW RATES PROGRAMMED** POINT B EXCLUSIVE - ...
From $1186 per night (USD)Expedia
From $1213 per night (USD)VRBO
Modern Farmhouse In Central Oak Bluffs Neighborhood
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
POINT B EXCLUSIVE - This newly-built Modern Farmhouse is tucked away in a quiet and centrally located neighborhood in Oa ...
From $1213 per night (USD)VRBO
From $428 per night (USD)Expedia
Please let us know in advance which ferry you’re on and arrival time.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fully equipped cottage behind the main house, Private, available all year round! Perfect romantic get away. Back Patio ...
From $428 per night (USD)Expedia
From $2207 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 $2207 per night (USD)VRBO
From $465 per night (USD)Expedia
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 ...
From $465 per night (USD)Expedia
From $363 per night (USD)VRBO
Sweet Little Post&Beam
- Bedrooms:
- 2
- 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 $363 per night (USD)VRBO
From $630 per night (USD)Expedia
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine
- Bedrooms:
- 3
- 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 $630 per night (USD)Expedia
From $985 per night (USD)VRBO
PRIME SUMMER WEEKS JUST REDUCED!! 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 $985 per night (USD)VRBO
From $960 per night (USD)Expedia
Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Surround yourself with comfort and fresh furnishings! This is a beautiful four-year-old home that is stylishly furnishe ...
From $960 per night (USD)Expedia
From $538 per night (USD)VRBO
Oak Bluffs Cottage - A Short Walk to the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $538 per night (USD)VRBO
From $637 per night (USD)Expedia
Water View Oasis 1 mi from Oak Bluffs 10 min Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked ...
From $637 per night (USD)Expedia
From $476 per night (USD)VRBO
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
- Bedrooms:
- 3
- 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 $476 per night (USD)VRBO
From $2266 per night (USD)Expedia
East Chop Beach House w\/Pool
- Bedrooms:
- 5
- 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 $2266 per night (USD)Expedia
From $475 per night (USD)VRBO
Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you are considering bringing your pet, please note - one small dog may be considered, but we ask that you send an ini ...
From $475 per night (USD)VRBO
From $1324 per night (USD)Expedia
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 $1324 per night (USD)Expedia
From $423 per night (USD)VRBO
Conveniently located near Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This comfortable home has all the amenities of home in an idyllic setting, easy access to town, beach and gorgeous East ...
From $423 per night (USD)VRBO
From $585 per night (USD)Expedia
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $585 per night (USD)Expedia
From $1376 per night (USD)VRBO
Walk to Beach and Town. Large Family House.
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
-Seven air conditioned bedrooms -Four bathrooms -One living room and two small sitting rooms -large bluestone patio wit ...
From $1376 per night (USD)VRBO
From $265 per night (USD)Expedia
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! Deck,A\/C,Outdoor Shower, Wifi
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $265 per night (USD)Expedia
From $440 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 $440 per night (USD)VRBO
From $492 per night (USD)Expedia
Delilah & Joseph Pierce House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Travel and Enjoy! Built by international artist, curator, educator, advocate, and diplomat Delilah W. Pierce, and her fa ...
From $492 per night (USD)Expedia
From $917 per night (USD)VRBO
Dog-friendly home with fenced yard- walking distance to beach, ferry & town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Wayland Victorian Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $917 per night (USD)VRBO
From $737 per night (USD)Expedia
Completely renovated, air conditioned cottage close to the beach. Dog friendly.
- Bedrooms:
- 4
- 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 $737 per night (USD)Expedia
From $605 per night (USD)VRBO
Location, Charm, & Steps to Town\/Beach -- Central AC, 100% Renewable Energy
- Bedrooms:
- 2
- Bathrooms:
- 5
- 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 $605 per night (USD)VRBO
From $1424 per night (USD)Expedia
Modern 4 bed\/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Enjoy everything the island has to offer in a spacious, custom-built, fully-stocked modern farmhouse and backyard oasis ...
From $1424 per night (USD)Expedia
From $734 per night (USD)VRBO
Close to town, beautifully updated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*** For stays between 9/1/2024 and 6/14/2025, Please inquire about a discounted cleaning rate***. Renovated Oak Blu ...
From $734 per night (USD)VRBO
From $643 per night (USD)Expedia
Convenient In-Town (Oak Bluffs) Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Great Vineyard location on Vineyard Avenue in Oak Bluffs. Built in 1920 and thoughtfully restored in 1999, this house is ...
From $643 per night (USD)Expedia
From $565 per night (USD)VRBO
Beautiful Contemporary Farmhouse close to Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautifully maintained contemporary farmhouse features an open floor plan. The first floor has an open kitchen, dining, ...
From $565 per night (USD)VRBO
From $1189 per night (USD)Expedia
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
- Bedrooms:
- 3
- 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 $1189 per night (USD)Expedia
From $693 per night (USD)VRBO
Ocean Views from East Chop
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
Easy access to Oak Bluffs or Vineyard Haven, quiet street overlooking Crystal Lake and the Vineyard Sound. House has fi ...
From $693 per night (USD)VRBO
From $967 per night (USD)Expedia
Multiple Ensuites, Central Air, Perfect Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Our home is approximate 2200sf and has 4 bedrooms including 3 bedrooms with en-suite bathrooms (all on second floor) an ...
From $967 per night (USD)Expedia
From $1252 per night (USD)VRBO
Gingerbread cottage with stunning Oak Bluffs Harbor View
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Amazing vacation spot Enjoy beautiful views of Oak Bluffs Harbor and beyond Historic gingerbread cottage Large front por ...
From $1252 per night (USD)VRBO
From $750 per night (USD)Expedia
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 $750 per night (USD)Expedia