Farm Pond 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 $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 $616 per night (USD)
Expedia
Perfect Family Home- Oak Bluffs, Martha's Vineyard
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Our wonderful family house is exactly what you're looking for to compliment your Martha's Vineyard vacation. The house' ...
From $616 per night (USD)Expedia
- From $425 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 $425 per night (USD)VRBO
- From $450 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 $450 per night (USD)Expedia
- From $415 per night (USD)
VRBO
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)VRBO
- 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 $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 $366 per night (USD)
Expedia
Coastal condo with pool, tennis courts & home comforts - close to beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 39G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $366 per night (USD)Expedia
- From $308 per night (USD)
VRBO
Dog-friendly first-floor seaside cottage with pool & tennis courts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Inn - 15D Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $308 per night (USD)VRBO
- From $355 per night (USD)
Expedia
Cute condo with pool & tennis - close to golf & the beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island Inn - 1A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $355 per night (USD)Expedia
- From $356 per night (USD)
VRBO
Charming suite with pool & tennis courts - 1\/2 mile to the beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 30G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $356 per night (USD)VRBO
- 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)
VRBO
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)VRBO
- From $730 per night (USD)
Expedia
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)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 $450 per night (USD)
VRBO
Dog-friendly townhouse with pool & tennis - easy walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 42G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $450 per night (USD)VRBO
- From $409 per night (USD)
Expedia
Deluxe townhouse with pool & tennis courts - half-mile to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Inn - 44G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $409 per night (USD)Expedia
- From $413 per night (USD)
VRBO
Sunny coastal retreat with pool & tennis - 1\/2 mile to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Inn - 49G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $413 per night (USD)VRBO
- From $379 per night (USD)
Expedia
Comfortable townhouse close to town & the beach with outdoor pool & tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 48G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $379 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Cozy seaside escape with on-site tennis, pool & prime location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Inn - 16D Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $357 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Stylish townhouse 1\/2 mile from the beach with tennis courts & pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 46G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $325 per night (USD)Expedia
- From $358 per night (USD)
VRBO
Dog-friendly suite with pool & tennis - golf & beach nearby
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Island Inn - 31G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $358 per night (USD)VRBO
- From $306 per night (USD)
Expedia
Coastal getaway 1\/2 mile from beach with pool & tennis courts - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 32G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $306 per night (USD)Expedia
- From $337 per night (USD)
VRBO
Lovely retreat 1\/2 mile from the beach with pool & 3 tennis courts
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 34G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $337 per night (USD)VRBO
- From $382 per night (USD)
Expedia
Lovely condo suite, close to golfing & the beach with pool & home comforts
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Island Inn - 37G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $382 per night (USD)Expedia
- From $328 per night (USD)
VRBO
Sunny, dog-friendly suite with tennis & pool - close to golf & beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 33G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $328 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Charming condo with pool & resort amenities - close to the beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 38G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $351 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Dog-friendly condo with pool - explore the parks & hit the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Inn - 8C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $371 per night (USD)VRBO
- From $398 per night (USD)
Expedia
Corner condo with tennis & swimming pool - close to beaches, golf & town
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 28G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $398 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Comfortable, dog-friendly condo with pool & tennis - perfect location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island Inn - 2A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $275 per night (USD)VRBO
- From $333 per night (USD)
Expedia
Comfortable & convenient Martha's Vineyard condo with pool - close to beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 36G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $333 per night (USD)Expedia
- From $386 per night (USD)
VRBO
Cozy townhouse with pool, tennis & great location close to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 43G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $386 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Dog-friendly condo suite with pool, tennis & picnic area - close to beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Island Inn - 29G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $321 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 $356 per night (USD)
Expedia
Dog-friendly condo with pool & tennis courts - golf & beach nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 40G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $356 per night (USD)Expedia
- From $356 per night (USD)
VRBO
Lovely townhouse with deck, pool & tennis - walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 50G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $356 per night (USD)VRBO
- From $372 per night (USD)
Expedia
Newly renovated, spacious townhouse with pool & tennis courts - close to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 45G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $372 per night (USD)Expedia
- From $401 per night (USD)
VRBO
Superb townhouse close to golf & the beach with deck, tennis & pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 51G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $401 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Ground-floor condo with pool & tennis courts - close to golf & beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Island Inn - 35G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $341 per night (USD)Expedia
- From $397 per night (USD)
VRBO
Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Inn - 47G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $397 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Cozy condo near the beach with pool, tennis & grills
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Island Inn - 10C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $332 per night (USD)Expedia
- From $496 per night (USD)
VRBO
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)VRBO
- From $1000 per night (USD)
Expedia
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)Expedia
- From $295 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $517 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- 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 $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 $440 per night (USD)
VRBO
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)VRBO
- From $355 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 $355 per night (USD)Expedia
- From $1268 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 $1268 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- 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 $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 $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 $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 $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 $300 per night (USD)
Expedia
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)Expedia
- 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 $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 $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 $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 $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 $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 $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 $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 $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
- 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
- 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
- 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 $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 $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 $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 $423 per night (USD)
VRBO
Charming townhouse with deck, pool & on-site tennis - walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Island Inn - 41G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $423 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