Lakeside Park Rentals
- From $1100 per night (USD)
VRBO
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
THE “SUMMER WIND” HOUSE - WALK TO EVERYTHING! We have completely renovated our 5-bedroom, 3-full bathroom home with cent ...
From $1100 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $675 per night (USD)Expedia
- From $778 per night (USD)
VRBO
Dog-Friendly Home w\/Amazing Fenced-In Yards, Private Washer\/Dryer, Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Farmhouse Fantasy Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $778 per night (USD)VRBO
- From $225 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 $225 per night (USD)Expedia
- From $650 per night (USD)
VRBO
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 $650 per night (USD)VRBO
- From $490 per night (USD)
Expedia
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w\/AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Best of both worlds! Quietly situated among beautiful trees with few neighbors plus it is walking distance to swim and O ...
From $490 per night (USD)Expedia
- From $593 per night (USD)
VRBO
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 $593 per night (USD)VRBO
- From $405 per night (USD)
Expedia
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 $405 per night (USD)Expedia
- From $762 per night (USD)
VRBO
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 $762 per night (USD)VRBO
- From $288 per night (USD)
Expedia
Cozy cottage 3\/4 mile from Oak Bluffs harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Family owned, newly renovated, and kept charming home in Oak Bluffs, 1/2 mile walk to East Chop Lighthouse and slightly ...
From $288 per night (USD)Expedia
- From $259 per night (USD)
VRBO
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 $259 per night (USD)VRBO
- From $961 per night (USD)
Expedia
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Oak Bluffs Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $961 per night (USD)Expedia
- Click For Pricing
Expedia
Ground-Floor Apartment with Screened Porch, Yard, Grill & WiFi - Dogs Welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Flamingo House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For PricingExpedia
- From $383 per night (USD)
Expedia
Quaint,,,Quiet..up island feel yet a short walk to to , x ,, z wn 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 $383 per night (USD)Expedia
- From $730 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 $730 per night (USD)VRBO
- From $425 per night (USD)
Expedia
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 $425 per night (USD)Expedia
- From $450 per night (USD)
VRBO
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 $450 per night (USD)VRBO
- From $415 per night (USD)
Expedia
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $415 per night (USD)Expedia
- From $364 per night (USD)
VRBO
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 $364 per night (USD)VRBO
- From $380 per night (USD)
Expedia
Charming Home with High-Speed WiFi, Washer\/Dryer, Furnished Deck, & Gas Grill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Casa Marianne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $380 per night (USD)Expedia
- From $449 per night (USD)
VRBO
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home, walk to town, ferry, 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 $449 per night (USD)VRBO
- From $447 per night (USD)
Expedia
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 $447 per night (USD)Expedia
- From $1671 per night (USD)
VRBO
Vintage Victorian with Nantucket Sound Views & AC | Walk 100 Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Vintage Victorian Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1671 per night (USD)VRBO
- From $339 per night (USD)
Expedia
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 $339 per night (USD)Expedia
- From $416 per night (USD)
VRBO
Walk to Beach, Downtown Shops, Dining & Attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $416 per night (USD)VRBO
- From $1200 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 $1200 per night (USD)Expedia
- From $592 per night (USD)
VRBO
Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the charm of Martha’s Vineyard at your leisure from this ideally located apartment. With 2 bedrooms and 1 bat ...
From $592 per night (USD)VRBO
- From $496 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 $496 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w\/AC and Auto ferry tics
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 10
The cottage is in restored original condition with many original features including hardwood floors, paned windows with ...
From $1000 per night (USD)VRBO
- From $295 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 $295 per night (USD)Expedia
- Click For Pricing
VRBO
Historic Beach Front Victorian Home
- Bedrooms:
- 5
- Bathrooms:
- 9
- Sleeps:
- 20
This home is sure to bring you and your family and/or friends an unforgettable vacation. Begin the day with unobstructed ...
Click For PricingVRBO
- From $517 per night (USD)
Expedia
Beautiful Beachfront Condo with Spectacular View in the Heart of Oak Bluffs!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely, spacious, and beautifully appointed oceanfront condo is just steps from the beach and a short walk to the ...
From $517 per night (USD)Expedia
- Click For Pricing
VRBO
Large Apartment - 5 minutes to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beautiful apartment is 4 minutes to downtown Oak Bluffs, 5 minutes to Eastville Point Beach, 6 minutes to State Beac ...
Click For PricingVRBO
- From $288 per night (USD)
Expedia
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 $288 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Akwaaba Manor 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 $1500 per night (USD)VRBO
- From $715 per night (USD)
Expedia
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 $715 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Oak Bluffs - Quiet Neighborhood. Walk to Town and Beaches!
- 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 $700 per night (USD)VRBO
- From $440 per night (USD)
Expedia
Beautiful Home \/ Walk to Town - July dates available
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful and spacious 3 bedroom and 2 bathroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape style home. ...
From $440 per night (USD)Expedia
- From $355 per night (USD)
VRBO
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 $355 per night (USD)VRBO
- From $1268 per night (USD)
Expedia
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 $1268 per night (USD)Expedia
- Click For Pricing
VRBO
Enjoy a Martha’s Vineyard vacation in this clean and beautiful apartment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautifully updated apartment is located minutes from Oak Bluffs beaches, shopping and restaurants. Enjoy meals in the ...
Click For PricingVRBO
- From $800 per night (USD)
Expedia
Beautiful Carriage House on the Chop
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Recently built, this spectacular 2 Bedroom carriage house is located on 3/4 acre estate on beautiful East Chop Drive. Th ...
From $800 per night (USD)Expedia
- From $336 per night (USD)
VRBO
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Brewster House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $336 per night (USD)VRBO
- From $536 per night (USD)
Expedia
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 ...
From $536 per night (USD)Expedia
- From $658 per night (USD)
VRBO
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 $658 per night (USD)VRBO
- From $731 per night (USD)
Expedia
'The Boat House:' Beachfront on Martha's Vineyard!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
With its idyllic oceanfront setting, private beach access, this 1-bedroom, 1-bath vacation rental is what dreams are mad ...
From $731 per night (USD)Expedia
- From $1400 per night (USD)
VRBO
Spacious Colonial Steps From Inkwell and Circuit Ave!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Classic Beauty in the heart of Oak Bluffs. The Pennacook House is a year-round (heating and AC!) 6 bedroom, 2.5 bathroom ...
From $1400 per night (USD)VRBO
- From $2548 per night (USD)
VRBO
Discount for August 17-Sept. 7. See Below
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
DISCOUNT AUGUST 17-SEPTEMBER 7 Flexible Turn Day- 4 Day Minimum 7 nights 10% - 10 nights 15% - 14 nights 20% This charmi ...
From $2548 per night (USD)VRBO
- From $850 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 $850 per night (USD)VRBO
- From $620 per night (USD)
VRBO
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 $620 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Three Bedroom Family Getaway in Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 6
Our Sweet Carol Lane home here on Martha's Vineyard is in a quiet neighborhood just over one mile away from the heart of ...
From $300 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Downtown Oak Bluffs, short walk to beach & town; transferable ferry res. avail.
- 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 $371 per night (USD)VRBO
- From $786 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 $786 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,
- Bedrooms:
- 4
- 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 $500 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $600 per night (USD)
VRBO
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 $600 per night (USD)VRBO
- From $696 per night (USD)
VRBO
Beach, Town, and Tennis - Central AC
- Bedrooms:
- 3
- 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 $696 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $670 per night (USD)
VRBO
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 $670 per night (USD)VRBO
- From $1739 per night (USD)
VRBO
Oceanfront Home - Walk to Everything
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
We have some auto ferry reservations available for key July bookings. Endless water views, fully updated, and steps fr ...
From $1739 per night (USD)VRBO
- From $858 per night (USD)
VRBO
The Island Collection MV: Experience a Luxury Getaway by the Lagoon
- Bedrooms:
- 4
- 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 $858 per night (USD)VRBO
- From $714 per night (USD)
VRBO
Cottage w\/ distant WATERVIEW, 0.2 miles off Circuit Ave, quiet & private
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
LAST-MINUTE DISCOUNTED RATE FOR WEEK OF 8/27-9/3 $3,500. WILLING TO CONSIDER LESS-THAN FULL WEEK RENTAL - PLEASE INQUIR ...
From $714 per night (USD)VRBO
- From $1414 per night (USD)
VRBO
Coastal Farmhouse With Connected Carriage House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Point B Exclusive - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice i ...
From $1414 per night (USD)VRBO
- From $851 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 $851 per night (USD)VRBO
- From $758 per night (USD)
VRBO
Magnificent Spacious Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This lovely and beautifully furnished three-story home is located in a quiet residential section of Oak Bluffs. It is a ...
From $758 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Sweet Get Away Suite, Private Beach &Tennis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beautiful suite has a private entrance, is a walk down an old fashioned dirt road to a private beach and also right ...
From $395 per night (USD)VRBO
- From $1410 per night (USD)
VRBO
Newly Renovated House - Quiet area, walk to Downtown Oak Bluffs and the harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This newly renovated (2021) single-level house in downtown Oak Bluffs is perfect for your island getaway. The house has ...
From $1410 per night (USD)VRBO
- From $357 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 $357 per night (USD)VRBO
- From $1100 per night (USD)
VRBO
Beach and downtown OB walkable! 5 Bedroom Victorian on the park.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
You will find this 5 Bedroom Victorian quite charming with its bright & cheery interior. Located right across from wide ...
From $1100 per night (USD)VRBO
- From $950 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 $950 per night (USD)VRBO
- From $875 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 $875 per night (USD)VRBO
- From $650 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 $650 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Oak bluffs cottage, Perfect for. Honeymoon! Summer rentals fill up early !
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fully equipped cottage behind the main house, Private, available all year round! Perfect romantic get away! Many guests ...
From $375 per night (USD)VRBO
- From $250 per night (USD)
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 ...
From $250 per night (USD)VRBO
- From $539 per night (USD)
VRBO
Oak Bluffs apartment, walk to town and beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 2 bedroom, 1 bath Cape style garage is just 3/4 of a mile to downtown Oak Bluffs! Our Cape's floor plan offers an o ...
From $539 per night (USD)VRBO
- From $1681 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 $1681 per night (USD)VRBO
- Click For Pricing
VRBO
Adorable Cottage STEPS from Downtown and Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Follow us on Instagram - @weepackeminn With a front porch with rocking chairs, a back deck and grill, and an outdoor sh ...
Click For PricingVRBO
- From $1205 per night (USD)
VRBO
NEW DISCOUNTS!\nGREAT OAK BLUFFS LOCATION! 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 $1205 per night (USD)VRBO
- Click For Pricing
VRBO
Perfect one bedroom garage apartment with A\/C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This charming one bedroom is perfect for a couple or small family looking for a great space and in a great location just ...
Click For PricingVRBO
- From $550 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 $550 per night (USD)VRBO
- From $869 per night (USD)
VRBO
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 $869 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $482 per night (USD)
VRBO
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 $482 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Nautical Oasis 10-min Walk to Downtown Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
The house is perfectly located to get to the best beaches (Katama Beach, Long Pond, Lambert’s Cove, etc.) on the Island ...
From $600 per night (USD)VRBO
- From $1031 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 $1031 per night (USD)VRBO
- From $1743 per night (USD)
VRBO
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 $1743 per night (USD)VRBO
- From $485 per night (USD)
VRBO
Charming Oak Bluffs Cottage on bike path & bus route. 1 mile to Eastville beach.
- 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 $485 per night (USD)VRBO
- From $1114 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 $1114 per night (USD)VRBO
- From $260 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 $260 per night (USD)VRBO
- From $325 per night (USD)
Expedia
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 $325 per night (USD)Expedia
- From $385 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 $385 per night (USD)VRBO
- From $1214 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 $1214 per night (USD)VRBO
- From $400 per night (USD)
VRBO
**WALK TO BEACHES,HARBOR,EVERYTHING!! *IN-TOWN OB! Deck,A\/C,Outdoor Shower, Wifi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
***PLEASE “ MESSAGE” MANAGER/OWNER ANNETTE FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" & ...
From $400 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Oak Bluffs Cottage - A Short Walk to the Beach!
- Bedrooms:
- 3
- 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 $475 per night (USD)VRBO
- From $455 per night (USD)
VRBO
Water View Oasis 1 mi from Oak Bluffs 10 min Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked ...
From $455 per night (USD)VRBO
- From $260 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 $260 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This beautifully landscaped, professionally decorated 1998 contemporary offers affordable luxury. Stately French doors, ...
From $425 per night (USD)VRBO
- From $975 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 $975 per night (USD)VRBO
- From $444 per night (USD)
VRBO
Delilah & Joseph Pierce House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Travel and Enjoy! Built by international artist, curator, educator, advocate, and diplomat Delilah W. Pierce, and her fa ...
From $444 per night (USD)VRBO
- From $587 per night (USD)
Expedia
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 $587 per night (USD)Expedia