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

Oak Bluffs Rentals

Filter

Popular Areas

From $622 per night (USD)
VRBO
Lovely two bedroom apartment with indoor fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It’s very cozy and comfortable, New Construction, if you like to do walk is close to the path and trial, ride bikes, it ...
From $622 per night (USD)
VRBO
From $1721 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 $1721 per night (USD)
Expedia
From $870 per night (USD)
VRBO
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 $870 per night (USD)
VRBO
Click For Pricing
Expedia
Oak Bluffs Summer Getaway Cape & Pet friendly!
Bedrooms:
3
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
Expedia
From $437 per night (USD)
VRBO
Tree Top Suite Get-Away
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 $437 per night (USD)
VRBO
From $1525 per night (USD)
Expedia
** Vineyard Vacation Retreat ** with HOT TUB
Bedrooms:
3
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 $1525 per night (USD)
Expedia
Click For Pricing
VRBO
Secluded but not Isolated home for all to enjoy
Bedrooms:
3
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 ...
Click For Pricing
VRBO
Click For Pricing
Expedia
3 BR cozy Vineyard Vacation Apartment
Bedrooms:
2
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 ...
Click For Pricing
Expedia
From $1525 per night (USD)
VRBO
**Vineyard Vacation Retreat** -3 BR
Bedrooms:
3
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 $1525 per night (USD)
VRBO
$Updated home with forest views, deck, firepit, fast WiFi - near town\/beaches$
Click For Pricing
Expedia
Updated home with forest views, deck, firepit, fast WiFi - near town\/beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
White Pearl Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
Expedia
From $561 per night (USD)
VRBO
Modern Family Home Walkable to Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unwind at this stunning newly renovated home with modern furnishing! The home is on a quiet, well-maintained private roa ...
From $561 per night (USD)
VRBO
From $1171 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 $1171 per night (USD)
Expedia
Click For Pricing
VRBO
Cute 4-BR House within walking distance of Circuit Avenue
Bedrooms:
3
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 ...
Click For Pricing
VRBO
From $695 per night (USD)
Expedia
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Fallen Oak Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $695 per night (USD)
Expedia
$Renovated Historic House \The Legacy House\$
From $723 per night (USD)
VRBO
Renovated Historic House \"The Legacy House\"
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
2 Blocks - walking distance to Inkwell Beach! Walking distance to Circuit Avenue, Ocean Park, and Oak Bluffs ferry. Pea ...
From $723 per night (USD)
VRBO
From $1288 per night (USD)
Expedia
Beautiful Custom Home In Oak Bluffs
Bedrooms:
4
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 $1288 per night (USD)
Expedia
From $1027 per night (USD)
VRBO
Indulge in the ultimate vacation experience at this exquisite custom log home.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Turnover days are Saturday to Saturday Experience the ultimate in luxury and relaxation in the exclusive Eastville area ...
From $1027 per night (USD)
VRBO
$Fully Renovated & Spacious home within walking distance of Oak Bluffs \/ Beaches$
From $671 per night (USD)
Expedia
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 $671 per night (USD)
Expedia
From $1479 per night (USD)
VRBO
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Bedrooms:
2
Bathrooms:
7
Sleeps:
14
Fantastic home available from May to October. Seven Bedrooms, one den with pull out couch, two bathrooms and a dreamy o ...
From $1479 per night (USD)
VRBO
From $1229 per night (USD)
Expedia
Famous Gingerbread Home the Seashrimp across from Harbor in downtown Oak Bluffs.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Year-round Oak Bluffs in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water ...
From $1229 per night (USD)
Expedia
From $753 per night (USD)
VRBO
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 $753 per night (USD)
VRBO
From $581 per night (USD)
Expedia
3-BR Oak Bluffs Escape - Quick Trip to Towns & Beaches!
Bedrooms:
3
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 $581 per night (USD)
Expedia
From $2979 per night (USD)
VRBO
Daniels House is your next vacation home in Oak Bluffs.
Bedrooms:
7
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 $2979 per night (USD)
VRBO
$Hideaway At Meadow View Farm\/Private Tennis Courts with Spacious Bedrooms$
From $870 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 $870 per night (USD)
Expedia
From $242 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 $242 per night (USD)
VRBO
From $843 per night (USD)
Expedia
Short walk to town!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Just on the outskirts of town in Oak Bluffs behind the Library is this lovely 3 Bedroom, 2.5 Bathroom home with Central ...
From $843 per night (USD)
Expedia
$Martha's Vineyard Home w\/ Deck < 1 Mi to Beach!$
Click For Pricing
VRBO
Martha's Vineyard Home w\/ Deck < 1 Mi to Beach!
Bedrooms:
3
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 $1279 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 $1279 per night (USD)
Expedia
$Oceanview East Chop Beach House - 4 Bed\/2 Bath - 5 min walk to beach$
From $1117 per night (USD)
VRBO
Oceanview East Chop Beach House - 4 Bed\/2 Bath - 5 min walk to beach
Bedrooms:
2
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 $1117 per night (USD)
VRBO
From $687 per night (USD)
Expedia
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 $687 per night (USD)
Expedia
From $774 per night (USD)
VRBO
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 $774 per night (USD)
VRBO
$Inviting, two-story home with a large yard, sunroom, balcony, & washer\/dryer$
From $611 per night (USD)
Expedia
Inviting, two-story home with a large yard, sunroom, balcony, & washer\/dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Gingerbread Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $611 per night (USD)
Expedia
Click For Pricing
VRBO
Family-built Oak Bluffs property in a wonderful location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Frazier Circle, Unit 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Family-built Oak Bluffs property in a great location with kitchens & hot tub
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Frazier Circle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Family-built Oak Bluffs property in a wonderful location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Frazier Circle, Unit 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
VRBO
$Charming cottage near the beach with a furnished deck, yard, & washer\/dryer$
From $643 per night (USD)
Expedia
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 $643 per night (USD)
Expedia
From $884 per night (USD)
VRBO
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 $884 per night (USD)
VRBO
$Historical house with wraparound porch, modern updates, enclosed yard, & W\/D$
From $876 per night (USD)
Expedia
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 $876 per night (USD)
Expedia
From $1374 per night (USD)
VRBO
Vineyard Social-Spacious 5BR Home in Oak Bluffs
Bedrooms:
5
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 $1374 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Book your next East Coast escape at this Oak Bluffs vacation rental! Conveniently located near downtown Oak Bluffs, this ...
From $436 per night (USD)
Expedia
$Spacious home in central location with beautiful patio, pool table, W\/D, & AC$
From $1035 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 $1035 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Centrally located Oak Bluffs property next to Bike Path
Bedrooms:
3
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 $783 per night (USD)
Expedia
From $597 per night (USD)
VRBO
September 2025 Available! 6 Beds! Near Ocean Park, Inkwell, Ferry, Flying Horses
Bedrooms:
3
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 $597 per night (USD)
VRBO
Click For Pricing
Expedia
Remodeled and historic, beautiful Oak Bluffs home. Walk to Town and Ferry.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This is a beautifully remodeled, and meticulously maintained house in Cottage City. The property is a short walk to town ...
Click For Pricing
Expedia
From $586 per night (USD)
VRBO
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $586 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Spectacular Martha's Vineyard Island Home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This is our beautiful home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overl ...
From $484 per night (USD)
Expedia
From $2425 per night (USD)
VRBO
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
Bedrooms:
2
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 $2425 per night (USD)
VRBO
From $908 per night (USD)
Expedia
Luxury Loft Historic Center Oak Bluffs
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
From $908 per night (USD)
Expedia
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 $1224 per night (USD)
Expedia
Big Beach House - Ocean Views!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. ...
From $1224 per night (USD)
Expedia
From $735 per night (USD)
VRBO
Beautiful Landscaped Grounds and Pond & Kayaks
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to paradise!!! This beautiful property is located in prestigious fresh pond estates. It sits tucked away in the ...
From $735 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without and per ...
From $609 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Oak Bluffs Retreat - The perfect getaway!
Bedrooms:
3
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 $598 per night (USD)
VRBO
$\The Carousel House\ - Ocean Park - Featured in New York Times$
From $1364 per night (USD)
Expedia
\"The Carousel House\" - Ocean Park - Featured in New York Times
Bedrooms:
3
Bathrooms:
7
Sleeps:
12
This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, Tha ...
From $1364 per night (USD)
Expedia
From $2170 per night (USD)
VRBO
Relaxing Beach Front Home
Bedrooms:
4
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 $322 per night (USD)
Expedia
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 $322 per night (USD)
Expedia
From $2169 per night (USD)
VRBO
Waterfront House On Oak Bluffs Harbor
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Rarely available, large 5 bedroom home with 2 bathrooms and an outside shower right on Oak Bluffs Harbor. Great for kids ...
From $2169 per night (USD)
VRBO
From $824 per night (USD)
Expedia
Architect-Designed Getaway In Bayes Hill
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
POINT B EXCLUSIVE - This architect-designed home is tucked away back in the Bayes Hill enclave, surrounded by conservati ...
From $824 per night (USD)
Expedia
From $448 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 $448 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Family cottage in Oak Bluffs. Close to town
Bedrooms:
2
Bathrooms:
3
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 $536 per night (USD)
Expedia
From $1043 per night (USD)
VRBO
Beautiful Oak Bluffs Home, Steps from the Lagoon
Bedrooms:
4
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 $1043 per night (USD)
VRBO
$Wooded Retreat with Private Deck, Full Kitchen, Washer\/Dryer, & Fast WiFi$
From $584 per night (USD)
Expedia
Wooded Retreat with Private Deck, Full Kitchen, Washer\/Dryer, & Fast WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Wooded Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $584 per night (USD)
Expedia
$New constructed Edgartown home with AC, and car ferry tkts avail. for 6\/28-7\/5$
From $632 per night (USD)
VRBO
New constructed Edgartown home with AC, and car ferry tkts avail. for 6\/28-7\/5
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Newly constructed home in Edgartown on the island of Martha's Vineyard within walking distance of Sengekontacket Pond. ...
From $632 per night (USD)
VRBO
$WATERFRONT Downtown Cottage w\/ Beach$
From $765 per night (USD)
Expedia
WATERFRONT Downtown Cottage w\/ Beach
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
This is one of the most unique properties on Martha's Vineyard. Located directly on the bustling Vineyard Haven harbor & ...
From $765 per night (USD)
Expedia
Click For Pricing
VRBO
Great update 3 BR near ferry with pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Recently updated 3 bedroom 2 bathroom near Vineyard Haven Ferry and downtown restaurants. Walk to local spots easily. ...
Click For Pricing
VRBO
From $864 per night (USD)
Expedia
FREE FERRY CAR RESV FOR JULY Beautiful Spacious home with Game room & Central AC
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Family friendly property, preferred for family vacations. *****FREE FERRY CAR Reservation Tickets for Sunday to Sunday ...
From $864 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Quintessential Vineyard Vacation Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NOTE: We rent only on a weekly basis and only from Sunday to Sunday. Abutting the State Forest, our three bedroom saltb ...
From $343 per night (USD)
VRBO
$Secluded waterfront oasis w\/private beach and mooring, dock, patio - 1 dog OK$
From $1454 per night (USD)
Expedia
Secluded waterfront oasis w\/private beach and mooring, dock, patio - 1 dog OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lily Hill Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $1454 per night (USD)
Expedia
$Vineyard Haven Guest House - Sleeps 4, A\/C, Walk to Town$
From $448 per night (USD)
VRBO
Vineyard Haven Guest House - Sleeps 4, A\/C, Walk to Town
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
The guest house has a queen bed upstairs (large combination master suite/living room with This End Up couch set, vaulted ...
From $448 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
This nautical themed, well lit, 2 bed/1 bath condo is 1/4 mile from the ferry terminal within the Causeway Harborview co ...
From $461 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Oakhaven Cottage! Beautiful, large light-filled bedroom upstairs, full bathroom (shower, bathtub), refreshin ...
From $470 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious, island home with fast WiFi, furnished deck & central AC - near town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
On Island Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For Pricing
Expedia
From $326 per night (USD)
VRBO
1 Bedroom Guest Cottage With Water View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cute one bedroom guest cottage with water views of Sengecontacket and the ocean. It is fully equipped and is air condit ...
From $326 per night (USD)
VRBO
Click For Pricing
Expedia
WEST TISBURY QUIET CLOSE TO TOWN AND BEACH
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Jeff Kaye welcomes you to my Island Home. Leave stress behind for you & your family as you get on the ferry for your ma ...
Click For Pricing
Expedia
From $508 per night (USD)
VRBO
Vineyard Haven, Quiet Setting Just Minutes from Ferry and Bus
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy a relaxing stay on the Vineyard in this recently renovated house. Embrace all Martha’s Vineyard has to offer, the ...
From $508 per night (USD)
VRBO
From $801 per night (USD)
Expedia
Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
With more than Fifty, 5-STAR REVIEWS, you can book with confidence. This beautifully appointed home features luxe furni ...
From $801 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Waterfront condo with scenic views of Vineyard Haven harbor and beyond
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Completely updated/renovated 1 bedroom (sleeps 4), 1bath condo with eat in kitchen. Fantastic views with private beach ...
From $389 per night (USD)
VRBO
From $1005 per night (USD)
Expedia
Waterfront Getaway With Beautiful Views Of Senge Pond.FERRY TICKETS AVAILABLE!!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This fully air-conditioned 3 bedroom cottage sits directly on Sengekontacket Pond in the town of Edgartown. You will be ...
From $1005 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Family-Friendly Tisbury Escape - Walk to Town
Bedrooms:
2
Bathrooms:
6
Sleeps:
8
Experience the magic of Martha’s Vineyard firsthand at this completely renovated ranch-style retreat! Boasting a large s ...
From $568 per night (USD)
VRBO
From $570 per night (USD)
Expedia
A Charming Vineyard Cottage Just Off the Pond
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Remember when summer vacations meant spending long perfect days near the water? This simple wooden Vineyard cottage wit ...
From $570 per night (USD)
Expedia
Click For Pricing
VRBO
Family Home That Is Walking Distance To Town and Ferry
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This 4 bedroom, 2 full bath home that has accommodations for 8 people is great for sitting in the sun filled dining room ...
Click For Pricing
VRBO
Click For Pricing
Expedia
West Tisbury Wooded Summer Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Cape nestled in amongst mature trees, maintained lawn and native plantings on 2 secluded acres at the end of a ...
Click For Pricing
Expedia
From $730 per night (USD)
VRBO
Airy, Quiet Vacation Rental Home, pool, tennis, FERRY TIX on MV
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Families and children feel right at home in this clean, comfortable, contemporary house with large living/dining area, f ...
From $730 per night (USD)
VRBO
$Cottage w\/ water views from front yard, central ac & fireplace$
From $773 per night (USD)
Expedia
Cottage w\/ water views from front yard, central ac & fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Home Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $773 per night (USD)
Expedia
From $456 per night (USD)
VRBO
A Vineyard Home Perfect For Family Gatherings
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
"A beautiful and private spot for your family vacation, reunion of friends, or just a space to be alone and create. This ...
From $456 per night (USD)
VRBO
From $637 per night (USD)
Expedia
Walking-distance to town, shops, restaurants & ferry!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gorgeous updated apartment only a 5 minute walk from downtown Vineyard Haven. Enjoy a large outdoor deck with distant (a ...
From $637 per night (USD)
Expedia
From $1095 per night (USD)
VRBO
Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautifully renovated Greek Revival home on the quiet end of the historic William Street District with modern addition a ...
From $1095 per night (USD)
VRBO
From $402 per night (USD)
Expedia
One Bedroom Private Cottage on Large Quiet Property.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Up island feel with down island convenience. The private cottage sits on a large serene property nestled between tall tr ...
From $402 per night (USD)
Expedia
$Entire Renovated Home w\/ JEEP Wrangler, Near Town, Private$
From $1787 per night (USD)
VRBO
Entire Renovated Home w\/ JEEP Wrangler, Near Town, Private
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious, modern, and privately situated home only 1.5 miles from downtown Vineyard Haven. Guests will have access to ou ...
From $1787 per night (USD)
VRBO
$5 min walk to the BEACH ON MARTHA'S VINEYARD. Beautiful, new, modern, 1BED\/1BATH$
From $192 per night (USD)
Expedia
5 min walk to the BEACH ON MARTHA'S VINEYARD. Beautiful, new, modern, 1BED\/1BATH
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
LONG TERM SUMMER RENTAL! Lower level, NY style beach apartment on Martha's Vineyard, 2 min walk to the beach, 2 min dri ...
From $192 per night (USD)
Expedia
From $806 per night (USD)
VRBO
charming bungalow -- walk to beach & downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A quintessential island vacation spot in this charming Vineyard Haven bungalow -- formerly owned by a legendary local se ...
From $806 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Guest House In Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax with the whole family at this peaceful place to stay. Experience island living at this one-bedroom, one-bathroom g ...
From $424 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Luxurious 5BR Retreat : Steps from the Waterfront
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to a unique contemporary style home! Just steps from the town landing, enjoy access to Sengekontacket Pond and N ...
From $716 per night (USD)
VRBO
From $1669 per night (USD)
Expedia
Downtown brand new construction 3 bed & 3 bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
More pics coming soon! Just finishing up furnishing the place and completing the landscaping. But we wanted to open up f ...
From $1669 per night (USD)
Expedia
From $632 per night (USD)
VRBO
Renovated Vineyard Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your charming vacation retreat! This recently renovated cottage is perfect for a summer escape to the Vineyar ...
From $632 per night (USD)
VRBO
From $2792 per night (USD)
Expedia
Harbor Front in Vineyard Haven! Brand New Construction - seconds from Town!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover a newly constructed 3-bed, 2.5-bath rental with captivating views of Vineyard Haven Harbor. Adjacent to the Ste ...
From $2792 per night (USD)
Expedia
From $1076 per night (USD)
VRBO
Gorgeous Edgartown Colonial with Heated Pool, Central Air, Car
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Plenty of space in this 10 room colonial situated on a lovely private acre a short distance to bike paths, Edgartown vil ...
From $1076 per night (USD)
VRBO
From $763 per night (USD)
Expedia
Edgartown Escape, Spacious 4 Br, Quite Conveniently Located
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Well appointed over sized cape with lots of windows in quiet wooded neighborhood on a paved dead-end street in Edgartown ...
From $763 per night (USD)
Expedia
From $1117 per night (USD)
VRBO
Elegant, spacious Home - Sleeps 12- Walk to town
Bedrooms:
6
Bathrooms:
6
Sleeps:
13
This modern home boasts +5,000 square feet of living space w/ three beautifully decorated floors, including state of the ...
From $1117 per night (USD)
VRBO
From $697 per night (USD)
Expedia
Sunny 2bedroom condo w pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Two bedroom condo lots of light overlooking Vineyard Haven harbor. Ten minute WALK to the ferry, town, local restaurants ...
From $697 per night (USD)
Expedia

Search Your Destination Now!

Oak Bluffs Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 548 Rentals