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Oak Bluffs Rentals

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From $1638 per night (USD)
VRBO
Soulas Martha's Vineyard Victorian Beach House, Walk to Inkwell Beach & Town
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 $1638 per night (USD)
VRBO
From $1035 per night (USD)
VRBO
BRAND NEW!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Beautiful, brand new 5 BR, 2.5 BA w/ outdoor shower Cape-Style Home on 1 Acre of land minutes away from downtown Oak Blu ...
From $1035 per night (USD)
VRBO
From $283 per night (USD)
VRBO
Renovated Cottage with nice yard and homey interior
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The property has a detached garage with a full guest suite above it. The garage and guest suite will be occupied during ...
From $283 per night (USD)
VRBO
From $794 per night (USD)
VRBO
Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
*** CONTACT HOST TO CONFIRM DATES BEFORE BOOKING**** *** CONTACT HOST FOR EARLY BIRD SPECIAL AND OFF-SEASON RATES*** * ...
From $794 per night (USD)
VRBO
From $703 per night (USD)
VRBO
Free Beach chairs & umbrella use Beautiful Spacious home, Game room & Central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Family friendly property, preferred for family vacations. ***Complimentary Beach Chairs , umbrella & Cooler use during ...
From $703 per night (USD)
VRBO
From $646 per night (USD)
Expedia
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Experience the magic of Martha's Vineyard in this newly renovated 3 bed, 3 bath retreat! The first floor features an ope ...
From $646 per night (USD)
Expedia
From $957 per night (USD)
VRBO
Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs
Bedrooms:
4
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 $957 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach
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 $400 per night (USD)
Expedia
From $348 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 $348 per night (USD)
VRBO
From $1383 per night (USD)
VRBO
In Town Historic Captain's house
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
An elegant historic Captain’s house 2 blocks to downtown, the ferry, town pier and beach, and restaurants. An expansive ...
From $1383 per night (USD)
VRBO
From $1123 per night (USD)
VRBO
Coastal Farmhouse With Connected Carriage House
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice i ...
From $1123 per night (USD)
VRBO
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 $1879 per night (USD)
VRBO
Grand Coastal-Style Estate In The Preserve
Bedrooms:
7
Bathrooms:
5
Sleeps:
12
POINT B EXCLUSIVE - This recently built luxury home features three floors of deluxe indoor living space, with nicely int ...
From $1879 per night (USD)
VRBO
From $949 per night (USD)
Expedia
68 Meadow View Rd. OB. Ferry tix for two cars available for Jul & Aug.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This spacious, well-decorated home is located in Meadow View Farms, Oak Bluffs - a quiet neighborhood of gracious custom ...
From $949 per night (USD)
Expedia
From $761 per night (USD)
VRBO
Ellen's MV Hideaway: Down island convenience, solitude, and lots of space!
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
DM me before booking! Ellen’s Hideaway is an impeccably renovated home offering quality, beauty, and comfort, a welcomin ...
From $761 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Guesthouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our 900 square foot guesthouse is a separate house detached from the main house. House is within driving distance to sev ...
From $462 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vineyard Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $465 per night (USD)
VRBO
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Expedia
Great update 3 BR near ferry with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently updated 3 bedroom 2 bathroom near Vineyard Haven Ferry and downtown restaurants. Walk to local spots easily. ...
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Expedia
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VRBO
Centrally located in OakBluffs on Martha’s Vineyard
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Oak Bluffs, MA: Welcome to the LightHouse! Brand new addition to the kitchen, dining room and porch. Outdoor shower and ...
Click For Pricing
VRBO
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
From $2394 per night (USD)
VRBO
9 Bedroom Home with Hot Tub, AC, Walk to Town!
Bedrooms:
6
Bathrooms:
9
Sleeps:
15
This spacious property has a main house and a guest house with separate kitchens (perfect for multiple couples/parties! ...
From $2394 per night (USD)
VRBO
From $405 per night (USD)
VRBO
IN-TOWN-WALK TO EVERYTHING! Adorable & Affordable! Cozy Cape Style Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $405 per night (USD)
VRBO
From $1512 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 $1512 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
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 $1229 per night (USD)
Expedia
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Bedrooms:
6
Bathrooms:
9
Sleeps:
18
The Dexter is the perfect place to stay on the Vineyard in ALL seasons. We have 9 bedrooms, 6.5 baths, an outdoor shower ...
From $1229 per night (USD)
Expedia
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
From $665 per night (USD)
VRBO
Near Beaches 4 Bedroom Contemporary on Private Cul-de-sac. Sunny Wooded Lot
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
We rent Sat to Sat. These weeks r left 7/5-12 and 8/9-16; 8/16-23 and 8/23-30. We have ferry tickets for ur vehicle for ...
From $665 per night (USD)
VRBO
From $745 per night (USD)
VRBO
Entire house walking distance from ferry
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Rudders Cottage, nestled within a quite neighborhood yet walking distance to downtown shops, restaurants, fer ...
From $745 per night (USD)
VRBO
From $687 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 $687 per night (USD)
VRBO
From $2098 per night (USD)
VRBO
Recently Completed! Exceptional Striking, Classic Colonial wth Water Access
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Sited beautifully on approx 3/4 acre lot in a very desirable neighborhood! This five Bedroom, five bath home is the defi ...
From $2098 per night (USD)
VRBO
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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 ...
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Expedia
From $956 per night (USD)
VRBO
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)
VRBO
From $391 per night (USD)
Expedia
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)
Expedia
From $463 per night (USD)
VRBO
Make 'Our Place' Your Place for Summer Vacation!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
'Our Place' is your location for vacation! 3 bedroom, 2 bath private home. Wooded location, just 1 mile to town and fe ...
From $463 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
A comfortable residence, this charming ranch has all the amenities for a perfect vacation. It's quiet location is 1.5 mi ...
From $541 per night (USD)
Expedia
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 $329 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 $329 per night (USD)
VRBO
From $959 per night (USD)
VRBO
NEW! Edgartown 3 BR 2 Bath Newly Remodeled Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Completely renovated home located less than 3 miles from the Edgartown center and conveniently located near bike path a ...
From $959 per night (USD)
VRBO
From $730 per night (USD)
VRBO
Beautiful MV Retreat - Central AC - Large Deck, Blue Stone Patio and Fire Pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Martha's Vineyard! Many of our guests return year after year, drawn by our property’s prime location, cleanli ...
From $730 per night (USD)
VRBO
From $1462 per night (USD)
VRBO
Luxurious Sengekontacket Contemporary With Water Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
POINT B EXCLUSIVE - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from m ...
From $1462 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 $497 per night (USD)
VRBO
Edgartown, Walk to Beach, AC, & Water Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2024 - Upgraded two bedrooms to king-size beds 2023 - All New Kitchen Appliances Our Edgartown beach house offers beau ...
From $497 per night (USD)
VRBO
From $1302 per night (USD)
VRBO
Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Nestled on a quiet road within walking distance to Oak Bluffs, this 3-bedroom house with a separate 1-bedroom guest hou ...
From $1302 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 $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 $827 per night (USD)
VRBO
Serene Home in Edgartown
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your new peaceful getaway on Martha’s Vineyard. Let our lovely home provide your family with a comfortable an ...
From $827 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 $994 per night (USD)
VRBO
WATERFRONT Downtown Cottage w/ Beach
Bedrooms:
1
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 $994 per night (USD)
VRBO
From $1687 per night (USD)
VRBO
Spectacular Classic Waterfront Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
33 Beach captures the essence of Martha's Vineyard. Built around the turn of the century as a stop for the New York Yach ...
From $1687 per night (USD)
VRBO
From $1030 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 $1030 per night (USD)
VRBO
From $1017 per night (USD)
VRBO
Luxurious Contemporary Near The Lagoon
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
POINT B EXCLUSIVE - This recently built luxurious Contemporary is quietly tucked away by The Lagoon and Martha's Vineyar ...
From $1017 per night (USD)
VRBO
From $583 per night (USD)
VRBO
Vineyard Haven, Close to town and Lake Tashmoo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful home located at the end of cul de sac in a quiet residential neighborhood. Nicely furnished interior with ce ...
From $583 per night (USD)
VRBO
From $307 per night (USD)
Expedia
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)
Expedia
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
From $475 per night (USD)
VRBO
Irie By The Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Irie by the Lake is a spacious, well-appointed 3 bedrooms 2 baths apartment with all modern amenities, located within wa ...
From $475 per night (USD)
VRBO
From $698 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 $698 per night (USD)
VRBO
From $311 per night (USD)
VRBO
Newly renovated charming modern island home for your relaxing getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This open concept, recently renovated summer home is on a one acre woodsy property. The bedroom has a queen size bed an ...
From $311 per night (USD)
VRBO
From $451 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 $451 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
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 $430 per night (USD)
VRBO
VH Bright and Airy Cottage - walking distance to downtown and beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summer Street MV - where the spirit of summer lives Welcome to our tranquil A-frame cottage nestled in the serene beaut ...
From $430 per night (USD)
VRBO
From $340 per night (USD)
Expedia
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 $340 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Awesome reviews, very private, conservation land, bike path and close to town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy this lush and private property set on a quiet street 2.5 miles from downtown Edgartown shops & restaurants and 4 m ...
From $548 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Sweet Retreat Newly Renovated And Stylish
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
POINT B EXCLUSIVE - This classic Cape, in the desirable Dodgers Hole neighborhood of Edgartown, has recently been renov ...
From $465 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 $938 per night (USD)
VRBO
Vineyard Haven Gem - A luxury rental on Martha's Vineyard
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This home is the perfect back drop for your vacation memories. This newly constructed home has a comfortable, modern a ...
From $938 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 $373 per night (USD)
VRBO
New construction Edgartown home with AC, new furnishings, o/d shower, bike path.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly constructed home in Edgartown on the island of Martha's Vineyard within walking distance of Sengekontacket Pond. ...
From $373 per night (USD)
VRBO
From $580 per night (USD)
Expedia
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)
Expedia
From $519 per night (USD)
VRBO
Edgartown Escape, Spacious 4 Br, Quite Conveniently Located
Bedrooms:
1
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 $519 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 $747 per night (USD)
VRBO
Gorgeous Edgartown Colonial with Heated Pool, Central Air, Car
Bedrooms:
3
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 $747 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in the desirable, private Meadow View Farms Estates, across from the Farm Neck Golf Club, this charmingly decora ...
From $450 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Serene Sengekontacket Pond Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The property is set among several private townhouses in a lovely neighborhood located off of Sengekontacket Pond in Oa ...
From $423 per night (USD)
VRBO
From $959 per night (USD)
Expedia
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)
Expedia
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 $484 per night (USD)
VRBO
Spectacular Martha's Vineyard Island Home!
Bedrooms:
2
Bathrooms:
3
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)
VRBO
From $276 per night (USD)
VRBO
Small One Bedroom Private Cottage on Large Quiet Property.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Small private cottage on a large quiet property nestled among tall trees with a wrap around deck. Perfect for a couple’s ...
From $276 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
From $1130 per night (USD)
VRBO
Elegant, spacious Home - Sleeps 12- Walk to town
Bedrooms:
4
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 $1130 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 $594 per night (USD)
VRBO
Easy Access to Beaches: Vineyard Haven House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Sunny Interiors w/ Large Windows | Walk to Shops, Restaurants & Ferry Terminal Plan an escape to Martha’s Vineyard and ...
From $594 per night (USD)
VRBO
From $246 per night (USD)
VRBO
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your next summer trip to Martha’s Vineyard starts at this vacation rental in Vineyard Haven! This 1-bedroom, 1-bathroom ...
From $246 per night (USD)
VRBO
$A View Fit for Royalty!\nTop Compliments: so clean! fab hot tub! best view!$
From $587 per night (USD)
Expedia
A View Fit for Royalty!\nTop Compliments: so clean! fab hot tub! best view!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The reviews say it all. We are a 5-star property because we surprise and delight our renters with not only a great hom ...
From $587 per night (USD)
Expedia
From $810 per night (USD)
VRBO
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)
VRBO
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 $5713 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 $5713 per night (USD)
VRBO
From $456 per night (USD)
VRBO
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $456 per night (USD)
VRBO
From $689 per night (USD)
Expedia
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $689 per night (USD)
Expedia

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