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From $729 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 $729 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Charming 3-bedroom house in OakBluffs, walking distance to Circuit Ave!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in Oak Bluffs, this delightful house offers 4 bedrooms including 1 king bed, 2 queen beds, and 1 bunk bed. With ...
From $661 per night (USD)
Expedia
From $707 per night (USD)
VRBO
Lovely peaceful MV 3-bedroom island home, sleeps 12, with air and comm. pool.
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Make yourself at home in our lovely 3-bedroom West Tisbury retreat. Perfect for families and friends looking for a peace ...
From $707 per night (USD)
VRBO
From $503 per night (USD)
VRBO
2-bedroom house, Short walk to beach, with AC and WiFi in Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private Home and yard a block from the Lagoon in Oak Bluffs. Easy walk to quiet neighborhood beach. Brand new kitchen/ba ...
From $503 per night (USD)
VRBO
From $977 per night (USD)
VRBO
Peaceful East Chop Vineyard 5-BR 3-BA home, AC, large yard, Guest apt add-on.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located in exclusive East Chop area of Oak Bluffs, enjoy what this 5-bedroom house has to offer. Walk to beach, a safe, ...
From $977 per night (USD)
VRBO
From $2872 per night (USD)
VRBO
WE’RE BACK! Oak Bluffs Retreat. NEW PRIVATE POOL -- FERRY TIX!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large beautifully appointed three bedroom, 2 1/2 bath house, with a den perfect for space for everyone to enjoy themselv ...
From $2872 per night (USD)
VRBO
From $3755 per night (USD)
VRBO
Main house and a separate apartment with saltwater pool, spa, outdoor cooking!
Bedrooms:
6
Bathrooms:
7
Sleeps:
12
Forget your worries in this spacious and serene space. Tucked away, the brand new compound offers all amenities. Heated, ...
From $3755 per night (USD)
VRBO
From $526 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 $526 per night (USD)
VRBO
From $822 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 $822 per night (USD)
VRBO
From $724 per night (USD)
VRBO
Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spectacular water views from classic Martha's Vineyard waterfront home! Perched atop a bluff overlooking the Nantucket ...
From $724 per night (USD)
VRBO
From $642 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 $642 per night (USD)
VRBO
From $870 per night (USD)
VRBO
Spacious Contemporary with Private Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Our gorgeous, sun swept 3000sq ft open floor plan contemporary water view home is perched on a hill overlooking Vineyar ...
From $870 per night (USD)
VRBO
From $6933 per night (USD)
VRBO
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $6933 per night (USD)
VRBO
From $1028 per night (USD)
Expedia
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 $1028 per night (USD)
Expedia
From $371 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 $371 per night (USD)
VRBO
From $646 per night (USD)
Expedia
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fallen Oak Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $646 per night (USD)
Expedia
From $1050 per night (USD)
VRBO
Beautiful Custom Home In Oak Bluffs
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Discover 4 spacious bedrooms with well planned living space with a inviting porch that wraps around 3/4 of the house is ...
From $1050 per night (USD)
VRBO
From $1730 per night (USD)
Expedia
Charming Vacation Home in Oak Bluffs.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Just a stone away from Oak Bluffs and its beaches, this chic 4 bedroom home provides comfort and privacy. The large bedr ...
From $1730 per night (USD)
Expedia
From $1502 per night (USD)
VRBO
** Vineyard Vacation Retreat ** with HOT TUB
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell dri ...
From $1502 per night (USD)
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 $679 per night (USD)
VRBO
3-BR Oak Bluffs Escape - Quick Trip to Towns & Beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape and exhale in this bright, airy 3-bedroom, 2.5-bathroom retreat that sleeps up to 7. Centrally located between Oa ...
From $679 per night (USD)
VRBO
From $719 per night (USD)
Expedia
Hideaway At Meadow View Farm/Private Tennis Courts with Spacious Bedrooms
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This Martha’s Vineyard Hideaway is nestled in the desirable Meadow View Farms area of Oak Bluffs, and includes access to ...
From $719 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Martha’s Vineyard studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio apartment on highly sought resort island of Martha’s Vineyard. 500 square feet with private entrance, bathroom, ...
From $246 per night (USD)
VRBO
From $723 per night (USD)
VRBO
Charming Oak Bluffs Retreat – Walk to Town, Harbor & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Just outside downtown Oak Bluffs, this 3-bedroom, 2.5-bath home features Central AC and an open layout ideal for gatheri ...
From $723 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $1295 per night (USD)
Expedia
Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Tiffany's Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1295 per night (USD)
Expedia
From $628 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 $628 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Charming Martha's Vineyard retreat close to beaches & downtown - large yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Set Sail Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $525 per night (USD)
Expedia
From $526 per night (USD)
VRBO
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 $526 per night (USD)
VRBO
From $830 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 $830 per night (USD)
Expedia
Click For Pricing
VRBO
Amazing sunsets. Beautiful 3 bedroom home on 4 acres near Lamberts Cove Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy stunning sunsets from this beautiful home set on 4 quiet acres near Lambert's Cove Beach. Relax and unwind in this ...
Click For Pricing
VRBO
From $689 per night (USD)
Expedia
Secluded Cottage, West Tisbury, Lambert's Cove Beach Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled in the woods of West Tisbury, this charming 2-bedroom +, 900 sq. ft. home, with additional sleeping loft, offers ...
From $689 per night (USD)
Expedia
From $871 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 $871 per night (USD)
VRBO
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Expedia
Cute 4-BR House within walking distance of Circuit Avenue
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
It is all about location! Leave the car at the house, and walk right into town. This 4 bedroom, 2 bath home features a l ...
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Expedia
From $623 per night (USD)
VRBO
Charming Family Home in the Heart of Martha's Vineyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This home is located on a private wooded lot and has 3BR/2.5B. On the first floor you will have an eat-in kitchen with a ...
From $623 per night (USD)
VRBO
From $1464 per night (USD)
Expedia
Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
Captain Shaw Norris House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $1464 per night (USD)
Expedia
Click For Pricing
VRBO
Oak Bluffs Summer Getaway Cape & Pet friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated cape in a quiet neighborhood near Lagoon Pond (1/2 mile away), 1.5 miles from downtown Oak Bluffs, very ...
Click For Pricing
VRBO
From $1214 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 $1214 per night (USD)
VRBO
From $1228 per night (USD)
VRBO
Rural Farm Location close to Town
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Sited on 28 acres with endless sky. All the amenities one could ask for. Tons of space and character on a former working ...
From $1228 per night (USD)
VRBO
From $366 per night (USD)
Expedia
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)
Expedia
From $870 per night (USD)
VRBO
Walk to town & beach A/C, Strong WiFi, family & pet friendly. Outdoor shower
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summertime! And the living is easy in this comfortable, casual home on Martha's Vineyard. The large front deck is great ...
From $870 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Spacious 1 Bedroom Apt - 3 min Walk to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A perfect place for 1-4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dinin ...
From $274 per night (USD)
VRBO
From $585 per night (USD)
VRBO
Oak Bluffs Retreat - The perfect getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Six minute drive to beach! This two floor beauty with central AC boasts ample yard space and all the amenities you look ...
From $585 per night (USD)
VRBO
From $2170 per night (USD)
VRBO
Relaxing Beach Front Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Perfect Vineyard Vacation: This beautiful beachfront home is on the east side of Lagoon Pond, in the town of Oak Blu ...
From $2170 per night (USD)
VRBO
From $1354 per night (USD)
VRBO
Private 14 Acre Waterfront Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfor ...
From $1354 per night (USD)
VRBO
From $754 per night (USD)
VRBO
Centrally located Oak Bluffs property next to Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our vacation rental in Oak Bluffs, Martha's Vineyard! Lovely home in the sought after Meadow View Farms commu ...
From $754 per night (USD)
VRBO
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $733 per night (USD)
VRBO
Architect-Designed Getaway In Bayes Hill
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
POINT B EXCLUSIVE - This architect-designed home is tucked away back in the Bayes Hill enclave, surrounded by conservati ...
From $733 per night (USD)
VRBO
From $947 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 $947 per night (USD)
VRBO
From $369 per night (USD)
VRBO
Family cottage in Oak Bluffs. Close to town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Bright cottage for a small family or friends getaway with a large yard for lounging and outdoor dining. One mile from d ...
From $369 per night (USD)
VRBO
From $2456 per night (USD)
VRBO
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This quintessential Vineyard cottage was built in the 1920's, and retains most of its original charm and character. Loca ...
From $2456 per night (USD)
VRBO
From $786 per night (USD)
VRBO
Beautiful Oak Bluffs Home, Steps from the Lagoon
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Come enjoy this beautifully designed home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An ...
From $786 per night (USD)
VRBO

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Tisbury Rentals

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Results: 352 Rentals