Lakeside Park, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Lakeside Park, Massachusetts on RentalSaver.com!

Lakeside Park Rentals

From $939 per night (USD)
VRBO
Modern Farmhouse In Central Oak Bluffs Neighborhood
Bedrooms:
3
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 $939 per night (USD)
VRBO
From $465 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 $465 per night (USD)
Expedia
From $681 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 $681 per night (USD)
VRBO
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Expedia
Secluded but not Isolated home for all to enjoy
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A lovely contemporary cape in East Chop with 3 bedrooms, loft & 2 full baths. High ceilings & skylights. A 1/2 mile walk ...
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Expedia
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VRBO
3 BR cozy Vineyard Vacation Apartment
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
3 BR apartment located on Circuit Ave walking distance to town. This unit feels like its own house. The kitchen and livi ...
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VRBO
From $1512 per night (USD)
Expedia
**Vineyard Vacation Retreat** -3 BR
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large ...
From $1512 per night (USD)
Expedia
From $531 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 $531 per night (USD)
VRBO
From $953 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 $953 per night (USD)
VRBO
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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 ...
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VRBO
From $956 per night (USD)
Expedia
Beautiful Carriage House on the Chop
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Recently built, this spectacular 3 Bedroom carriage house is located on 3/4 acre estate on beautiful East Chop Drive. Th ...
From $956 per night (USD)
Expedia
From $391 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 $391 per night (USD)
VRBO
From $1361 per night (USD)
VRBO
Inca Gardens Apt. New To Market - Lg Patio - Pets
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's Vineyard between Oak Bluffs an ...
From $1361 per night (USD)
VRBO
From $1065 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 $1065 per night (USD)
VRBO
From $195 per night (USD)
VRBO
Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Build in 2020 ! New lovely studio apartment. Clean, bright and comfortable. 700 sq feet ! Great for couples, work trip ...
From $195 per night (USD)
VRBO
From $317 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 $317 per night (USD)
VRBO
From $397 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 $397 per night (USD)
VRBO
From $795 per night (USD)
VRBO
Beach and downtown OB walkable! 5 Bedroom Victorian on the park.
Bedrooms:
1
Bathrooms:
5
Sleeps:
11
You will find this 5 Bedroom Victorian quite charming with its bright & cheery interior. Located right across from wide ...
From $795 per night (USD)
VRBO
From $1030 per night (USD)
Expedia
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Location!!! Location!!! This updated cottage is a quick walk to town, beach, Tony’s Deli, tennis and basketball courts, ...
From $1030 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Make Lasting Memories In This Adorable Vineyard Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This quaint cottage, nestled in a quiet neighborhood of Oak Bluffs, is perfect for a romantic getaway, a special place t ...
From $307 per night (USD)
VRBO
From $415 per night (USD)
VRBO
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated three-level home with 3 bedrooms 2 bathrooms within walking distance to the heart of Downtown Oak Bluffs ...
From $415 per night (USD)
VRBO
From $782 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 $782 per night (USD)
VRBO
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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 ...
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Expedia
From $1228 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 $1228 per night (USD)
VRBO
From $1304 per night (USD)
VRBO
Oceanfront Home - Walk to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Please note this property is currently for sale. As a result, we are not accepting any rental bookings until December 1, ...
From $1304 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Yellow Brick Road House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $278 per night (USD)
VRBO
From $754 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 $754 per night (USD)
VRBO
From $580 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 $580 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Downtown Oak Bluffs, short walk to beach & town
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 $527 per night (USD)
VRBO
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 $606 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 $606 per night (USD)
VRBO
From $790 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 $790 per night (USD)
VRBO
From $686 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 $686 per night (USD)
VRBO
From $670 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 $670 per night (USD)
VRBO
$Your \Vineyard Dream\ Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town$
From $452 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 $452 per night (USD)
VRBO
From $1093 per night (USD)
VRBO
Indulge in the ultimate vacation experience at this exquisite custom log home.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Turnover days are Saturday to Saturday Experience the ultimate in luxury and relaxation in the exclusive Eastville area ...
From $1093 per night (USD)
VRBO
From $810 per night (USD)
Expedia
Luxury Loft Historic Center Oak Bluffs
Bedrooms:
2
Bathrooms:
6
Sleeps:
14
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
From $810 per night (USD)
Expedia
From $1013 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 $1013 per night (USD)
VRBO
From $2905 per night (USD)
VRBO
Vacation In This Historic And Luxurious Martha's Vineyard Home
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Perched on the corner of Ocean Park overlooking Nantucket Sound and across the street from the beach, this elegant home ...
From $2905 per night (USD)
VRBO
From $734 per night (USD)
VRBO
Charming, gracious cape 3 minute walk to private beach on Lagoon. Dog-friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely classic Vineyard cape located on a very quiet dead end street with access to a private sandy beach on the Lagoon. ...
From $734 per night (USD)
VRBO
$Renovated Historic House \The Legacy House\$
From $700 per night (USD)
Expedia
Renovated Historic House \"The Legacy House\"
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
2 Blocks - walking distance to Inkwell Beach! Walking distance to Circuit Avenue, Ocean Park, and Oak Bluffs ferry. Pea ...
From $700 per night (USD)
Expedia
From $902 per night (USD)
VRBO
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave
Bedrooms:
0
Bathrooms:
4
Sleeps:
10
New rental! Get away from it all in this Oak Bluffs secluded family friendly home offering 4 bedrooms, 2 full bathrooms, ...
From $902 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Family friendly, walking distance to town, harbor, shops, restaurants, beaches
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Canary Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $354 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Family home located near everything needed for the perfect vacation.
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
The house was recently renovated with new appliances and other furnishing. Appliances include a convection oven, dishwas ...
From $568 per night (USD)
VRBO
From $987 per night (USD)
Expedia
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Nestled in the charming town of East Chop, this 3-bedroom vacation home offers the perfect escape for your next getaway. ...
From $987 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Walk to OB Restaurants, Shopping, Harbor & Beaches! Winter monthly rental avail.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful, open concept, fully furnished home is just footsteps to Sunset Lake, harbor, beaches, entertainment, res ...
From $447 per night (USD)
VRBO
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Expedia
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Marsh Walk Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
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Expedia
From $1393 per night (USD)
VRBO
Enchanting bungalow with golf nearby, full kitchen, central AC, & washer/dryer
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
East Chop 90 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1393 per night (USD)
VRBO
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Expedia
GingerBread Cottage at Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Resort may charge damage deposit fees, cleaning fees, activities fees, and applicable Resort lodging taxes. Intimate Ho ...
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Expedia
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VRBO
Vineyard charm island memories
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Great location,wonderful front porch,incredible kitchen,outdoor gas grill,walking distance to downtown,beaches,A/C,Marth ...
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VRBO
From $479 per night (USD)
Expedia
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Pinkletink Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $479 per night (USD)
Expedia
From $738 per night (USD)
VRBO
COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in the beautiful Lagoon Heights neighborhood, you'll enjoy this lovely 3 Bedroom, 2 Bath cozy Cape Cod home with ...
From $738 per night (USD)
VRBO
From $585 per night (USD)
VRBO
Private setting nestled in the heart of East Chop.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great East Chop (Oak Bluffs) location! Take morning walks on world famous East Chop Drive, or watch the sunset from ther ...
From $585 per night (USD)
VRBO
From $1229 per night (USD)
VRBO
Famous Gingerbread House named Seashrimp across from Oak Bluffs Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Year-round in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water restaurants ...
From $1229 per night (USD)
VRBO
From $742 per night (USD)
Expedia
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to “Gem of the Ocean”! Martha’s Vineyard vacationers dream! This recently updated condo with private balcony and ...
From $742 per night (USD)
Expedia
From $1255 per night (USD)
VRBO
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Bedrooms:
2
Bathrooms:
7
Sleeps:
16
Fantastic home available from May to October. Seven Bedrooms, one den with pull out couch, two bathrooms and a dreamy o ...
From $1255 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landsc ...
From $658 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown ...
From $428 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $211 per night (USD)
VRBO
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VRBO
Martha's Vineyard Home w/ Deck < 1 Mi to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the beauty of Martha’s Vineyard when you stay at this charming 3-bedroom, 2.5-bathroom vacation rental! Situate ...
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VRBO
From $638 per night (USD)
VRBO
Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Bright air conditioned house has common space living TV room, dining and kitchen together. 1st floor has 1 bedroom with ...
From $638 per night (USD)
VRBO
From $1672 per night (USD)
VRBO
Daniels House is your next vacation home in Oak Bluffs.
Bedrooms:
6
Bathrooms:
9
Sleeps:
18
Breath taking views from this newly restored quintessential 1899 Oak Bluffs Cottage style home. It is equipped with 9 la ...
From $1672 per night (USD)
VRBO
From $732 per night (USD)
VRBO
Charming Oak Bluffs Retreat – Walk to Town, Harbor & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just outside downtown Oak Bluffs, this 3-bedroom, 2.5-bath home features Central AC and an open layout ideal for gatheri ...
From $732 per night (USD)
VRBO
From $582 per night (USD)
VRBO
Historical house with wraparound porch, modern updates, enclosed yard, & W/D
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Victorian by the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $582 per night (USD)
VRBO
From $936 per night (USD)
VRBO
Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
The perfect vacation awaits you at Frog Prince Cottage in beautiful East Chop, the finest neighborhood in Oak Bluffs. Ou ...
From $936 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes (2 Miles) to Downt ...
From $447 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Gingerbread Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $461 per night (USD)
Expedia
From $884 per night (USD)
VRBO
Location , Location , Location ! Walking distance to the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bellavista at the Seaview. This oceanfront condo is a coveted two bedroom , two bathroom home that was comple ...
From $884 per night (USD)
VRBO
From $1124 per night (USD)
VRBO
Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Perched on a grassy hill, this majestic home has sweeping views of Oak Bluffs Harbor and is just minutes from East Chop ...
From $1124 per night (USD)
VRBO
From $550 per night (USD)
VRBO
September 2025 Available! 6 Beds! Near Ocean Park, Inkwell, Ferry, Flying Horses
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
6 Bedrooms with incredible location will comfortably allow your family to vacation in the best part of Oak Bluffs. The l ...
From $550 per night (USD)
VRBO
From $2376 per night (USD)
VRBO
Gorgeous 7BR/6BA Ocean views Walk to Beach & Town - 10% off two week stay!
Bedrooms:
6
Bathrooms:
7
Sleeps:
10
Large Private Home formerly known as the SeaSpray Inn and featured on the reality television show "The Vineyard", this l ...
From $2376 per night (USD)
VRBO
From $1174 per night (USD)
VRBO
Oak Bluff's Victorian Walk to Town & Beaches
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
About this space First floor has AC and hosts windowed living, dining, work space, kitchen and garden bedroom that sleep ...
From $1174 per night (USD)
VRBO
From $460 per night (USD)
Expedia
New 2 min from Circuit ave
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
* new for 2025: Gameroom with pool table and ping pong table. * Welcome to this beautifully renovated home, located wit ...
From $460 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Charming cottage near the beach with a furnished deck, yard, & washer/dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Birds of Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $511 per night (USD)
VRBO
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Expedia
Quaint and pristine home with private suites and baths.
Bedrooms:
2
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 Pricing
Expedia
From $1189 per night (USD)
VRBO
Heart of Oak Bluffs - A Newly Renovated Gem, 5 Minute Walk to Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the perfect blend of location and luxury in this beautifully renovated charmer, centrally situated in Oak Bluff ...
From $1189 per night (USD)
VRBO
From $584 per night (USD)
Expedia
Walking to the beach. Bars and Restaurants.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Walking distance to the beach. 5 minutes away from downtown, steamship, ice cream, and restaurants. Lovely backyard with ...
From $584 per night (USD)
Expedia
From $869 per night (USD)
VRBO
Charming home near downtown & beach with patio, outdoor shower, grill, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Blissful Island Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $869 per night (USD)
VRBO
From $726 per night (USD)
Expedia
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2 Decks, hot tub and close to everything. Has all new stainless appliances, wi-fi, cable, grill, about one mile walk t ...
From $726 per night (USD)
Expedia
From $543 per night (USD)
VRBO
1 Bedroom, Sleeps 4; perfect small family vacation home
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Close to town and beach, but far enough away for peaceful quiet. 1 Bedroom; 3.5 bath; outdoor shower; front and side por ...
From $543 per night (USD)
VRBO
From $465 per night (USD)
VRBO
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)
VRBO
From $785 per night (USD)
VRBO
Exquisitely Comfortable 4bdrm 3ba Home w/ Large Yard in Oak Bluffs!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Gloria’s Cottage – A Martha’s Vineyard Retreat Step into the warmth of Gloria’s Cottage, a beautifully appoi ...
From $785 per night (USD)
VRBO
$Welcome to \Suzy's Place\ Best Location! Walk Everywhere. Newly built in 2024.$
From $728 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 $728 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Charming studio with amazing location near town & beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sankofa Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $286 per night (USD)
VRBO
From $487 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 $487 per night (USD)
Expedia
From $851 per night (USD)
VRBO
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Bird Street Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $851 per night (USD)
VRBO
From $447 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 $447 per night (USD)
Expedia
From $684 per night (USD)
VRBO
House with guest studio close to town and beach with grill, games, AC & patio
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Sankofa Martha's Vineyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $684 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Book your next East Coast escape at this Oak Bluffs vacation rental! Conveniently located near downtown Oak Bluffs, this ...
From $366 per night (USD)
VRBO
From $1201 per night (USD)
VRBO
Modern Cottage Walk To Town & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy one of Oak Bluffs’ newest accommodations perched at the peak of the Highlands boasting just a 10 minute walk to to ...
From $1201 per night (USD)
VRBO
From $738 per night (USD)
VRBO
Charming 3-bedroom house in Oak Bluffs with AC, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to Noble House, your ideal getaway on Martha’s Vineyard. Nestled in the heart of Oak Bluffs at 21 Pheasant Lane, ...
From $738 per night (USD)
VRBO
From $1235 per night (USD)
VRBO
Steps to Inkwell Beach: Victorian Home!
Bedrooms:
2
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 $1235 per night (USD)
VRBO
From $868 per night (USD)
Expedia
NEWLY RENOVATED! Quiet location, walk to Circuit Avenue and beaches!
Bedrooms:
3
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 $868 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to your home away from home! Experience the charm of Oak Bluffs in this spacious 3-bedroom, 2.5-bathroom beautif ...
From $633 per night (USD)
VRBO
From $1023 per night (USD)
VRBO
Vineyard Social-Spacious 5BR Home in Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fant ...
From $1023 per night (USD)
VRBO
From $726 per night (USD)
VRBO
Charming 3-bedroom w/loft.New Construction home with AC,WiFi. Short walk to town
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This Oak Bluffs home boasts 3 inviting bedrooms and a cozy loft, including 2 king beds, 2 full beds and a queen sofa bed ...
From $726 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Island Inn - One Bedroom Suite - 10C - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This suite is a charming and cozy retreat, ideal for a relaxing getaway. It features a comfortable queen bed, ...
From $464 per night (USD)
Expedia
From $949 per night (USD)
VRBO
Island Inn - Cottage - 21E - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming first-floor corner two-bedroom, each with a Queen Bed, an additional full Sofa-bed ...
From $949 per night (USD)
VRBO
From $677 per night (USD)
VRBO
Quiet Getaway Within Walking Distance Of All Oak Bluffs Has To Offer.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
An enchanting Cape Cod cottage nestled on a quiet road with Farm Pond and ocean views. Share family dinners and conversa ...
From $677 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Oak Bluffs 3-Bedroom Victorian Cottage, Steps from Sunset Lake/Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Step Into Vineyard history—with a modern twist. Originally part of the historic Methodist Campground in Oak Bluffs, this ...
From $447 per night (USD)
VRBO
From $3483 per night (USD)
VRBO
Spacious 9-bedroom house with Waterview, WiFi, AC in delightful Oak Bluffs
Bedrooms:
4
Bathrooms:
9
Sleeps:
18
Get ready to relax in this 9-bedroom house in Oak Bluffs. This superb property boasts 3 king beds, 5 full beds, and 2 tw ...
From $3483 per night (USD)
VRBO

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