We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Oak Bluffs, MA

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 400 Rentals in Oak Bluffs
loading...
Sort by
From
$215
Per Night
1 / 8
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
From
$4,905
Per Week
1 / 22
6 Bedrooms, 3 Bathrooms, Sleeps 12
Details Reviews (1) Make Enquiry
From
$1,962
Per Week
1 / 16
5 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
From
$2,207
Per Week
1 / 19
4 Bedrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stunning views at this waterfront vacation rental home on the Lagoon in Oak Bluffs. Enjoy beautiful summer days lounging on the deck or sticking your toes in the sand at the beach in front of the house. House offers easy living with an open living room/dining room. Two bedrooms on the main level,... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 June 2014
Not sure what was better, the fritters from Back Door Donuts in nearby OB (off Kennebec Street) or the refreshing breezes right off the lagoon?! Gold stars all around for this...
See all reviews
From
$276
Per Night
1 / 17
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This bright and charming 3 bedroom, 1.5 bath house rests outside downtown Oak Bluffs. The house boasts 3 bedrooms, 1.5 baths, an open living room/kitchen combination, 2 decks and an outside eating area. The first floor bedroom contains a full sized bed. A half bath with laundry is across the... View all property information
Make Enquiry
5 of 5 stars Reviewed 28 August 2013
Stayed in this cute little house with 6 adults and 2 children. It was perfect! It is within walking distance to downtown OakBluffs. Walked there every morning and back to the...
See all reviews
From
$3,066
Per Week
1 / 20
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This great vacation home is an “upside down” home located in the private association neighborhood of Meadow View Farms. Its first floor has 3 bedrooms, laundry and large bathroom. The second floor has a great open living/dining room with side den, updated kitchen perfect for any size family, and... View all property information
Make Enquiry
From
$172
Per Night
1 / 20
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This spacious condo is an ideal vacation rental for a small family, a couple or two couples looking for clean, comfortable accommodations with the amenities needed to ensure a relaxed vacation. This large 2 bedroom end unit (1200 sq ft + large deck) is bright and airy. Downstairs has new hardwood... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 August 2014
We just finished our MV vacation and we had a great time. The condo is perfectly located between Edgartown, Vineyard Haven and OaksBluff. The bike trails are literally right out...
5 of 5 stars Reviewed 6 August 2013
We had a great relaxed vacation at this condo. It is a quiet and in a scenic and greenery neighborhood. The two-story apartment is perfect for a couple and small family with 3-4...
See all reviews
From
$613
Per Night
1 / 26
Payment Protection
5 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
5 BR, 2 full BA, 2 half BA, sleeps 10 Recently renovated Victorian home located in the historic Copeland District just one block from Oak Bluff's Inkwell beach. Three story home with decks and wrap around porch with ocean views from each. Five large bedrooms, spacious living room with brick... View all property information
Make Enquiry
5 of 5 stars Reviewed 26 October 2014
We stayed here in June of 2014 and had a great time. The house sleeps 10 people comfortably so it's nice for two families or a large extended family. It is steps from two beaches...
See all reviews
From
$307
Per Night
1 / 11
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This charming Cape style Oak house residence is situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area... View all property information
Make Enquiry
From
$521
Per Night
1 / 7
Payment Protection
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Cozy family owned property located in Oak Bluffs section of Martha's Vineyard. It is a home away from home. This property is walkable to town and less than 10 min. walk to Oak Bluffs Marina. 10 mins to the Gingerbread Cottages. The house sits back in a very quiet and private cul-de-sac area.... View all property information
Make Enquiry
Get the List
From
$491
Per Night
1 / 17
Payment Protection
4 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dishwasher. There is a portable... View all property information
Make Enquiry
5 of 5 stars Reviewed 23 August 2014
So often descriptions fall short of reality but our stay at this Flip-key rental was as it was toted, a "Charming Farmhouse." The four bedrooms were sweet and spacious decorated...
See all reviews
From
$368
Per Night
1 / 11
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious... View all property information
Make Enquiry
4 of 5 stars Reviewed 2 September 2013
The location is optimal for teens as they can walk around town and enjoy 2am donuts. The roof deck has a 2 great views one of harbor and one of ocean the other two views not so...
See all reviews
From
$264
Per Night
1 / 40
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 7
Booking
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This welcoming home is freshly renovated and decorated in calm and comfortable Vineyard style, with hand-hewn, antique and designer furnishings. The house is ideally located on a quiet street, within easy walking distance to the village, harbor, beaches, waterfront parks and historic Victorian... View all property information
Make Enquiry
5 of 5 stars Reviewed 21 September 2014
A great time was had by everyone! This house was exactly as described but the best part was dealing directly with the owner and knowing that they were only a phone call away if...
5 of 5 stars Reviewed 5 September 2013
I stayed in this lovely Oak Bluffs home in mid-August. It was pristine, nicely decorated and well-appointed. It's a very spacious house with plenty of room to spread out, relax or...
See all reviews
From
$159
Per Night
1 / 20
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (40) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 December 2014
My family loves the central location of this property! The front porch provides loads of free entertainment! The BEST spot!
5 of 5 stars Reviewed 17 October 2014
I just love this place! I have stayed here many times & always look forward to returning the next year. I love the ambiance of the place itself & I also love the location, it is...
See all reviews
From
$3,740
Per Week
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This newer home faces Nashawena Park, one of Oak Bluffs loveliest neighborhoods. From this excellent location, you are within walking distance of Inkwell Beach and all that Circuit Avenue has to offer - shops, excellent restaurants, the busy harbor area and ferry terminals, movies and nightly live... View all property information
Make Enquiry
From
$4,047
Per Week
1 / 15
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath juccuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
Make Enquiry
From
$1,226
Per Week
1 / 10
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,... View all property information
Make Enquiry
From
$2,453
Per Week
1 / 14
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The quintessential Vineyard cottage!!! This sweet cottage brings back visions of the lazy days of summer of bygone eras when life was less hurried. The serene location overlooks a pond, a barrier beach with a few homes, and the Outer Harbor. It has a magnificent 180 degree view of Vineyard... View all property information
Make Enquiry
From
$8,584
Per Week
1 / 19
7 Bedrooms, 6 Bathrooms, Sleeps 14
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same home while giving... View all property information
Make Enquiry
From
$3,066
Per Week
1 / 14
4 Bedrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
HIDDEN COVE, Martha's Vineyard - lovely four bedroom home with views of Sengekontacket Pond. Contemporary house with open kitchen, living and dining. Air conditioning in living room, kitchen/dining room, and all bedrooms. Ceiling fans in the 3 downstairs bedrooms. Large deck off back of house... View all property information
Make Enquiry
From
$3,188
Per Week
1 / 21
5 Bedrooms, 4 Bathrooms, Sleeps 13
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities include:... View all property information
Make Enquiry
4 of 5 stars Reviewed 12 August 2013
Nice, clean, updated home with space for everyone. We divided older teen girls in upstairs dorm style rooms that slept 5 from you get boys and girls in two rooms that slept 2 and...
See all reviews
From
$491
Per Night
1 / 30
Payment Protection
6 Bedrooms, 2 Bathrooms, Sleeps 13
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
*6 bedrooms, 2 full bathrooms + outdoor shower, sleeps 13 *1800+ sq. ft of living space (fully renovated and freshly painted) *2 NEWLY REBUILT BEDROOM-BALCONIES, 1 w/ a water-view - beautifully restored! *400 sq. ft wrap-around front porch with water view and comfortable seating for 11+ (4 rocking... View all property information
Make Enquiry
5 of 5 stars Reviewed 1 October 2014
Favorite things were outdoor shower and front porch (with rocking chairs and great dining table area). Great location - walking distance to the water (which you can see from...
See all reviews
From
$2,453
Per Week
1 / 12
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Sun filled and airy pond front contemporary home with beautiful views of Lagoon Pond. Four bedrooms accommodating up to eight guests. Two full baths plus refreshing outdoor shower. The second floor with its cathedral ceiling utilizes an open living room, dining room and kitchen floor plan to... View all property information
Make Enquiry
From
$1,472
Per Week
1 / 21
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The... View all property information
Make Enquiry
From
$7,217
Per Week
1 / 20
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Luxury waterfront home with dock, deep water mooring, a private beach as well as deep water access and marina facilities close-by. Enjoy a commanding view of Lagoon Pond with gorgeous westerly sunsets - second to none! This home offers a spacious open floor plan providing a comfortable yet elegant... View all property information
Make Enquiry
From
$5,764
Per Week
1 / 21
8 Bedrooms, 3 Bathrooms, Sleeps 16
Details Reviews (2) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The living room, sunporch and kitchen... View all property information
Make Enquiry
From
$4,231
Per Week
1 / 16
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Set back well off the road, this special Island home and it's surrounding open grounds are in a perfect mid-Island location for easy access to towns and beaches. It is very near to a wonderful bike path! The large living room has a tiny balconied and is graced by a an interesting, hand painted,... View all property information
Make Enquiry
From
$3,066
Per Week
1 / 15
3 Bedrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Three level Hillside Condominium corner unit. Top floor with master bedroom offering views of Sengekontacket Pond and the ocean. Lowest of three levels has two bedrooms which open to the ground level in the back. Convenient to both Oak Bluffs and Edgartown Center. Association pool and tennis... View all property information
Make Enquiry
From
$362
Per Night
1 / 10
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Come Stay aboard Martha's Vineyard's ONLY FLOATING Bed and Breakfast! Celebrating our 5th season!! MS Resolute is a classic 40 ft Islander Cutter Sailboat docked at the picturesque Oak Bluffs Marina. Experience a unique boating adventure without ever leaving the dock. Enjoy romantic sunsets, be... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 August 2014
My husband and I just returned from a 3 night stay on the Resolute - Bed and Breakfast Afloat and had a wonderful time. We took the Island Queen ferry in from Falmouth and had...
3 of 5 stars Reviewed 11 August 2014
My girlfriend and I stayed here for 4 nights. The place is charming and Susan and John the host and hostess very gracious. We were blessed with great weather. Sitting on the...
See all reviews
From
$1,656
Per Week
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
With Inkwell Beach at your door step, sweeping ocean views from your private deck and Living Room, and walk-to-town convenience, this Waterside Condo offers a unique vacation getaway in Oak Bluffs. Located directly across the street from popular Inkwell Beach, the second floor condo enjoys sweeping... View all property information
Make Enquiry
From
$1,104
Per Night
1 / 21
Payment Protection
5 Bedrooms, 5 Bathrooms, Sleeps 10
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our newly renovated home guarantees a perfect vacation on the Vineyard. This 5 bedroom house is across the street from Nantucket Sound. Sit back and relax on the spacious front porch - catch the sun and the moon rise over the Atlantic Ocean. It features 5 spacious bedrooms, 5 bathrooms, 2 large... View all property information
Make Enquiry
1 of 5 stars Reviewed 16 October 2014
I'm writing this review because I tried at least a dozen times to contact this owner. The owner has a "book it" option where my credit card woud be immediately chargers, but she...
See all reviews
From
$245
Per Night
1 / 11
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This airy home captures the spirit of easy island life and makes you feel like you've gotten away. It's secluded on a quiet, wooded, paved, dead-end street, the second house from the end. Yet it's centrally located in the East Chop area of Oak Bluffs for easy access to the beaches (.25 miles to... View all property information
Make Enquiry
From
$385
Per Night
1 / 24
5 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat-screen LED TV's with cable service; Located 10-20 min walk to Oak Bluffs harbor, beach... View all property information
Make Enquiry
From
$331
Per Night
1 / 7
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Our picture-perfect home is an excellent summer escape. Spacious double lot makes this setting seem like a parkland. It's just a 15-minute walk to downtown Oak Bluffs and the town beach. It's also on the public transit line and the bike path. View all property information
Make Enquiry
Enquire for rates
1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Lovely two bedroom, 2 bath condo unit with sweeping water views. Town center is but a 5 minute walk from the condo complex where you will find, family and fine dining, shops. groceries, the famous Flying Horse Carousel,- a great attraction for children and the young at heart. Stroll along the... View all property information
Make Enquiry
From
$337
Per Night
1 / 9
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
Make Enquiry
From
$613
Per Night
1 / 8
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A fully renovated four bedroom home with three and a half baths and separate garage, landscaped lot and a private dock. Dock can accommodate up to a 25 foot motor boat and is accessible to Vineyard Sound. Family room with cable TV, deck, fully equipped kitchen, wood burning stove, and a 2 person... View all property information
Make Enquiry
From
$258
Per Night
1 / 7
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 7
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... View all property information
Make Enquiry
From
$582
Per Night
1 / 10
Payment Protection
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
Make Enquiry
Enquire for rates
1 / 18
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful three bedroom two and a half bath home located in Oak Bluffs. Walking distance from the lagoon and beach. Close proximity to downtown Oak Bluffs and the beaches. Large backyard and deck and finished basement. Queen sofa bed in basement. Additional amenities include: beach chairs,... View all property information
Make Enquiry
From
$736
Per Night
1 / 9
Payment Protection
5 Bedrooms, 2 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Across the street from the renowned Inkwell beach and just minutes to walk to town, harbor and the ferry. This large classic victorian beach house was built in 1851. The property has a beach studio next door which can be rented for larger groups. A large classic wrap around porch with ocean... View all property information
Make Enquiry
From
$491
Per Night
1 / 11
Payment Protection
4 Bedrooms, 1 Bathroom, Sleeps 8
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
New Renovated, 1870 historic 'Campground' cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly... View all property information
Make Enquiry
From
$276
Per Night
1 / 9
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a bright kitchen/dining/living... View all property information
Make Enquiry
From
$4,905
Per Week
1 / 18
Payment Protection
4 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
For those discriminating vacationers who love returning 'home' from the beach, a shopping spree or a sail, to dine alfresco, enjoy an outdoor nap, marvel at the sunsets and watch boating on Vineyard Sound, this 4 bedroom home (freshly painted!) and its porch and grounds are the perfect spot - -... View all property information
Make Enquiry
Enquire for rates
1 / 26
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Cinderella Cottage ~ Charming Oak Bluffs Victorian located walking distance to town and two blocks to the beach.  Not right on the main road but so close to everything! The house has four spacious bedrooms, three baths, a well equipped kitchen, two living rooms and a very nice dining room. There is... View all property information
Make Enquiry
5 of 5 stars Reviewed 15 October 2013
We stay at the Pequot every year for Columbus Day weekend and we will keep coming back for as long as we are able! We have a great family reunion here every year, where family...
See all reviews
From
$472
Per Night
1 / 9
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
4 bedrooms.3 baths, sleeps 8 The house is tucked away on a quiet, homey road, just a short walking distance to Circuit Avenue – the hub of Oak Bluffs activity! Here, you will enjoy the best of both worlds; whether you prefer to relax in the quiet, inviting and comfortable surroundings of this four... View all property information
Make Enquiry
From
$552
Per Night
1 / 44
Payment Protection
6 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
*New lower Winter/spring rates only $1200/week! *multi-week discount available *Only 3 prime summer 2013 weeks left! Check my calendar and book ASAP if you plan to visit in the peak season. The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained,... View all property information
Make Enquiry
From
$368
Per Night
1 / 17
6 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Waterview - located on the East Chop Vineyard Highlands overlooking Nantucket Sound, Oak Bluffs harbor, Sunset Lake, and 3 acre Washington Park, this charmingly original 1860's Vineyard cottage is an ideal family vacation home. Leave the car on the mainland or in the driveway, for everything,... View all property information
Make Enquiry
From
$1,839
Per Night
1 / 34
Payment Protection
6 Bedrooms, 3 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Historic summer 'cottage' with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in... View all property information
Make Enquiry
Enquire for rates
1 / 15
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Modern, spacious, family friendly home, located 250 steps from the Lagoon beach for swimming, clamming, boating, beaching, and sunset watching.The main floor has a granite kitchen, open living and dining area, 1/2 bath with laundry facilities and master bedroom with shower and deck. The second... View all property information
Make Enquiry
5 of 5 stars Reviewed 5 July 2014
Stayed at this house for a week with my wife and two young children. Very easy to get to and is a five minute drive to downtown Oak Bluffs and ten minutes to State Beach. Very...
See all reviews
Go to map view
Book Online(23)
Use filters to find the best results!

Suitability

  • Wheelchair access (2)
  • Elder access (15)
  • Suitable for children (4)
  • Pet friendly (19)
  • Smoking allowed (1)

Amenities

  • Internet (367)
  • Grill (350)
  • Other outdoor space (310)
  • Air Conditioning (209)
  • Washer/Dryer (170)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List