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.

Vacation rentals in Cuttyhunk, MA and nearby

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
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 250 Rentals in the Cuttyhunk Area
loading...
From
$698
Per Night
View Details
1 / 7
Payment Protection
Cuttyhunk
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
From
$174
Per Night
View Details
1 / 18
Payment Protection
Cuttyhunk
8 Bedrooms, 8 Bathrooms, Sleeps 22
Details Make Enquiry

The following rentals are within 15 kilometres of Cuttyhunk, Massachusetts.

From
$401
Per Night
View Details
1 / 10
Payment Protection
Chilmark
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
From
$372
Per Night
View Details
1 / 26
Payment Protection
Chilmark
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Stereo System
  • Ceiling Fans
  • DVD Player
  • Refrigerator
  • Porch
  • Microwave
  • Air Conditioning
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This small cottage on a hill, built in the 1950's, has been updated for comfort and style while maintaining the feel of the old-time Vineyard. One bedroom, one bathroom, a computer room, and a great room that includes kitchen, living, and dining area fit comfortably into 450 square feet. Many... View all property information
Make Enquiry
From
$343
Per Night
View Details
1 / 14
Payment Protection
Aquinnah
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (6) Make Enquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Built in 2007, this ocean front home has a private trail through rolling sand dunes down to a white sand beach that stretches for miles. Right out front is Dog Fish Bar, a world class fishing location. Sand bars stretch for a mile right out front making for great adventuring at low tide. A great... View all property information
Make Enquiry
5 of 5 stars Reviewed 26 November 2014
I didn't think the house and views could exceed the gorgeous pictures posted, but they do! First time to Martha's Vineyard, myself, my 2 sons and their girlfriends (from NY, NJ...
5 of 5 stars Reviewed 5 October 2014
Perfect place for people who want to be away from the crowds and enjoy privacy. The house is clean, tidy, beautifully furnished and even better than the photos. Very spacious...
See all reviews
From
$4,069
Per Week
View Details
1 / 25
Aquinnah
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Dishwasher
  • VCR
  • Dryer
  • Microwave
  • TV
  • Satellite TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Bright and breezy post & beam home sitting on 3-acres of rolling wooded land located down a private road. Southern views of the Atlantic ocean as well as a short drive/bike to Philbin and Lobsterville beaches and the Gay Head cliffs. This very Vineyard home offers 3-levels w/two queen bedrooms, a... View all property information
Make Enquiry
From
$1,738
Per Week
View Details
1 / 12
Payment Protection
Chilmark
2 Bedrooms, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • TV
  • Refrigerator
  • Ceiling Fans
  • Satellite TV
  • Internet Access
  • DVD Player
  • Stereo System
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Great location. Menemsha Village. 2 bedroom cottage. Sunny interior. 1 bath, plus outdoor shower. Storage barn, cable tv, High Speed internet, washer. Walk to beach, harbor, dock, stores, restaurants. Currently available August only. $1595 per week. 2 wk minimum. Maximum occupancy 2 adults,... View all property information
Make Enquiry
From
$1,046
Per Night
View Details
1 / 30
Payment Protection
Chilmark
5 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Dryer
  • Dishwasher
  • Washer
  • Refrigerator
  • Ceiling Fans
  • Microwave
  • Parking
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the... View all property information
Make Enquiry
From
$6,394
Per Week
View Details
1 / 18
Chilmark
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • TV
  • Patio
  • Ceiling Fans
  • Grill
  • Fireplace
  • Washer
  • Deck
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Expansive distant waterviews overlooking Vineyard Sound on three and a half acre property. Located in desirable Spring Point, this 40 home association is accessed by a private, well maintained dirt roads with 40 acres of common land consisting of nature trails and a private beach on the Sound. This... View all property information
Make Enquiry
From
$291
Per Night
View Details
1 / 24
Payment Protection
Aquinnah
2 Bedrooms, 2 Bathrooms, Sleeps 3
Bookings
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Parking
  • Microwave
  • DVD Player
  • TV
  • Satellite TV
  • Deck
  • Terrace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This house is the perfect spot for enjoying the beauty and calm of Aquinnah. Light-filled, inviting and private, the house has multiple levels and sits on over an acre of wooded land with stone walls and a stream running through the property. Inside, the house offers wood floors throughout, a... View all property information
Make Enquiry
Get the List
From
$523
Per Night
View Details
1 / 10
Payment Protection
Aquinnah
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • DVD Player
  • TV
  • Ceiling Fans
  • Dryer
  • Refrigerator
  • Washer
  • Parking
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Lovely, easy, breezy vacation home with secret garden, acres of privacy, birdsong and oceanbreezes and views will make your stay relaxing and restore your senses and refresh your body mind and soul. We offer an ECO Green house, providing only the best 100% Cotton linens and towels, energy star... View all property information
Make Enquiry
From
$3,627
Per Week
View Details
1 / 14
Menemsha
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
  • Deck
  • Dryer
  • Satellite TV
  • Hot Tub
  • Microwave
  • TV
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Welcome to Menemsha! This 3 bedroom home is located on a 2.3 acre wooded lot in a very quiet setting with superb water views toward the Elizabeth Islands. The private yard has a wooden deck for outdoor grilling and dining. The interior is comfortable and clean. The first floor Master bedroom has a... View all property information
Make Enquiry
5 of 5 stars Reviewed 1 July 2013
If I could take this house and bring it home I would!! What a charming cottage all decorated in a nautical theme just as I expected. The cleanest place I"ve stayed so far. Loved...
See all reviews
From
$3,953
Per Week
View Details
1 / 13
Payment Protection
Aquinnah
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (1) Make Enquiry
Amenities & Details
  • Refrigerator
  • Fireplace
  • Grill
  • Parking
  • Ceiling Fans
  • DVD Player
  • Dryer
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Private beach with mooring!Hot fishing spot known as Dogfish bar!Beautiful renovated home.1 minute walk to the beach through our deeded sand dune!Views through out this home.It has everything! Granite kitchens and baths! Seating for at least 12. Open floor plan. Hardwood floors. 3 BR 2 Full... View all property information
Make Enquiry
4 of 5 stars Reviewed 22 July 2014
Open and spacious home that had an amazing backyard for our kids to run around. Ocean views and French doors that made every morning and evening inviting. We loved our stay at...
See all reviews
From
$3,488
Per Week
View Details
1 / 32
Payment Protection
Aquinnah
4 Bedrooms, 2 Bathrooms, Sleeps 12
Details Reviews (2) Make Enquiry
Amenities & Details
  • Patio
  • Towels Provided
  • Washer
  • DVD Player
  • Refrigerator
  • Satellite TV
  • # Of Bathrooms
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Aquinnah Cliffs, Gay Head, farm house, private, ocean views, Martha's Vineyard, Vineyard, Philbin Beach. Enjoy ultimate privacy with expansive ocean views and walking distance to area beaches. The farm house has a beach feel with a large lawn, multiple patios, a deck and privacy all around. The... View all property information
Make Enquiry
From
$2,907
Per Week
View Details
1 / 15
Chilmark
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Washer
  • Guest Count
  • Dishwasher
  • Grill
  • Stereo System
  • Dryer
  • TV
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located on South Road near Able's Hill, this family oriented house comes with access to a private South Shore beach across Chilmark Pond. Have fun boating, kayaking or canoeing across the pond to the beach. A family room in the lower level provides space for the younger members of the family to... View all property information
Make Enquiry
From
$2,907
Per Week
View Details
1 / 22
Aquinnah
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Patio
  • DVD Player
  • Fax
  • Microwave
  • Dishwasher
  • TV
  • Dryer
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This beautiful home affords breathtaking views of the Vineyard Sound. You'll enjoy the best of the south end of the Island, including access to Philbin and the colorful Cliffs beaches. There's also Lobsterville and West Basin for calmer waters and hungry fishermen! This home will suit the most... View all property information
Make Enquiry
From
$748
Per Night
View Details
1 / 45
Payment Protection
Chilmark
5 Bedrooms, 4 Bathrooms, Sleeps 9
Details Reviews (6) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fax
  • Microwave
  • DVD Player
  • Washer
  • TV
  • Refrigerator
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This comfortable contemporary home located up-island in Chilmark, includes a key to a private beach, Blackpoint, and is ideal for laid-back Vineyard living, or elegant entertaining with both ocean and hillside view. The open floor plan for the common areas bring the outdoors inside with spectacular... View all property information
Make Enquiry
From
$4,825
Per Week
View Details
1 / 10
Chilmark
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Ceiling Fans
  • Deck
  • Satellite TV
  • Microwave
  • TV
  • DVD Player
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Situated on a cul-de-sac overlooking a private meadow with spreading oaks ensures privacy. The screened porch, meadow bench, hammock and second floor deck off the master bedroom provide quiet spots to get away. Amenities and Features include... Wifi, A/C in Master Additional amenities include:... View all property information
Make Enquiry
4 of 5 stars Reviewed 11 August 2014
Great vacation. Home was clean, property is private and quiet and as always, very comfortable. Convenient location for our family vacation needs. Lack of recycling at house...
See all reviews
From
$698
Per Night
View Details
1 / 64
Payment Protection
Chilmark
3 Bedrooms, 4 Bathrooms, Sleeps 9
Details Reviews (3) Make Enquiry
Amenities & Details
  • Dryer
  • Hot Tub
  • Washer
  • Refrigerator
  • Microwave
  • TV
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Sprawling Hilltop Glass House admits views and entertains peace from every angle. Large south facing stone terrrace has hot tub and large table to enjoy guests and family. Please note: The calendar may not display the 1st and last dates of booked property as this house may turn over on the same... View all property information
Make Enquiry
5 of 5 stars Reviewed 15 August 2013
This was a fabulous family retreat. Plenty of bathrooms, very comfortable beds, and a great outdoor patio for grilling or lounging. We hope to come back next year!
See all reviews
From
$2,325
Per Week
View Details
1 / 12
Chilmark
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Internet Access
  • Microwave
  • Deck
  • Grill
  • TV
  • DVD Player
  • Satellite TV
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming newly renovated cottage features large screened porch and private deck. Porch is fully furnished for dining and relaxing. Ten minutes to famous Lucy Vincent Beach and the same distance to West Tisbury village and Alley's General Store. Amenities and Features include... Screened Porch,... View all property information
Make Enquiry
From
$4,650
Per Week
View Details
1 / 22
Chilmark
4 Bedrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Satellite TV
  • Fireplace
  • Stereo System
  • Microwave
  • Water Views
  • Dishwasher
  • Internet Access
  • Waterfront
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Chilmark waterfront rental home located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This martha's vineyard rental property offers private dock, mooring along with access to small beach area just down the path on Clam Point Cove. Named appropriately, it... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 September 2014
Our family thoroughly enjoyed our week at the Mayhew home in Chilmark. We rented kayaks for some boating right off the private pier, picked clams, swam off the docked and cooked...
See all reviews
From
$581
Per Night
View Details
1 / 55
Payment Protection
Chilmark
3 Bedrooms, 1 Bathroom, Sleeps 7
Details Reviews (4) Make Enquiry
Amenities & Details
  • Grill
  • Satellite TV
  • Deck
  • Refrigerator
  • Microwave
  • Dishwasher
  • Internet Access
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This home is 1/2 mile from Chilmark Center If you are having trouble with FERRY RESERVATIONS contact me via email or phone and I'll work with you for a shorter stay if need be or assist you. This home is minutes to both Lucy Vincent Beach (with both nude and regular bathing sections) and... View all property information
Make Enquiry
4 of 5 stars Reviewed 7 July 2014
Just spent a very relax vacation in this country style house that gived us a family home feel outside of our home. The house is surround by green trees with beautiful wood logs...
See all reviews
From
$2,907
Per Week
View Details
1 / 23
Chilmark
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Internet Access
  • VCR
  • Microwave
  • Stereo System
  • DVD Player
  • Deck
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Unique waterfront living in the heart of Chilmark. The Boathouse sits directly on the shores of Stonewall Pond, with sweeping water views of the Pond, Stonewall Beach and the Atlantic Ocean. You also have access to Stonewall Beach -- one of Chilmark's most prestigious private association beaches.... View all property information
Make Enquiry
5 of 5 stars Reviewed 27 December 2013
we have stayed in this property 3 years running in both June and July. It's the most peaceful spot imaginable (no mobile phone signal) with unending wildlife activity ( we have...
See all reviews
From
$2,325
Per Week
View Details
1 / 22
Chilmark
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Microwave
  • TV
  • Dishwasher
  • Fax
  • Grill
  • Fireplace
  • Deck
  • Waterfront
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 June 2014
We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and...
See all reviews
From
$3,488
Per Week
View Details
1 / 24
Aquinnah
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Microwave
  • Fireplace
  • DVD Player
  • Patio
  • Satellite TV
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Fabulous House, Fabulous Views. Attention to detail throughout. A dream gourmet kitchen. Ocean Views from all of the bedrooms. 180 degree views from Squibnocket to Aquinnah South Shores. Stunning sunsets from the west porch, sometimes referred to as the Martini deck! Brilliant sunrises from the... View all property information
Make Enquiry
From
$1,163
Per Week
View Details
1 / 12
Menemsha
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Washer
  • Grill
  • Stereo System
  • Dryer
  • Wi-Fi
  • TV
  • Satellite TV
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
What a location! Located in Menemsha with classic Vineyard fishing village views this cottage is the quintessential vacation home. You can walk to the beach to picnic, fish or watch beautiful sunsets and you can also walk to one of the Island's most popular seafood restaurants. It is light, airy... View all property information
Make Enquiry
From
$4,069
Per Week
View Details
1 / 16
Menemsha
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Satellite TV
  • Grill
  • Washer
  • Dryer
  • DVD Player
  • Microwave
  • TV
  • Waterfront
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Vineyard cottage with gorgeous views of Chilmark Pond and beyond. Located at Quitsa Pond Overlook. Owners have verbal agreement with dock owners to use the dock for short term use on, no tie-ups. Mooring & dingy available. Wheelchair access. Additional amenities include: dock/boat-slip, coffee... View all property information
Make Enquiry
From
$4,825
Per Week
View Details
1 / 15
Aquinnah
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • VCR
  • Toaster
  • TV
  • Dishwasher
  • Satellite TV
  • Microwave
  • Internet Access
  • Waterfront
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Completely renovated beachfront home. Set on gorgeous Aquinnah North Shore beach. Relax on the decks overlooking the water or stroll to the beach down your private path. Truly a peaceful retreat. Amenities and Features include... Waterfront, Hi Speed Internet Additional amenities include:... View all property information
Make Enquiry
From
$4,883
Per Week
View Details
1 / 30
Menemsha
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • TV
  • Air Conditioning
  • Microwave
  • Satellite TV
  • Internet Access
  • Dishwasher
  • DVD Player
  • Water Views
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Don't miss this rare opportunity to vacation in a beautifully renovated 275 year old antique New England Cape. Private beach front on Menemsha Pond is a short walk from the house. Built in the 1700's for Captain John Pease and his wife, Hannah, this 3 bedroom home is steeped in history and has been... View all property information
Make Enquiry
From
$3,488
Per Week
View Details
1 / 19
Chilmark
4 Bedrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Telephone
  • Internet Access
  • Microwave
  • Fax
  • Deck
  • Toaster
  • Blender
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Elegant Architectural Digest Cape home in Chilmark, in pristine condition. Many fine details to this Martha's Vineyard vacation home. Custom woodwork, antique heart pine floors and fireplaces. Luxury construction (as compared to custom) built in 1998. Custom cabinetry with gourmet kitchen. Meadowed... View all property information
Make Enquiry
From
$1,860
Per Week
View Details
1 / 17
Aquinnah
3 Bedrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Blender
  • Stereo System
  • Grill
  • Deck
  • Telephone
  • Dishwasher
  • Microwave
  • Toaster
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This well built, hardwoods throughout and beautifully decorated Cape Cod style home is nestled on a dirt road in amongst a year round neighborhood. For those morning or evening walks you are just a short distance to the Sengekontacket Pond boat launch full of natural wildlife. This property has... View all property information
Make Enquiry
From
$2,325
Per Week
View Details
1 / 8
Chilmark
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Internet Access
  • Dishwasher
  • TV
  • Dryer
  • Satellite TV
  • Microwave
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view of the Sound over the tree tops from the full length deck...dine inside comfort of screened-in porch. Convenient kitchen opens into living... View all property information
Make Enquiry
From
$2,907
Per Week
View Details
1 / 9
Aquinnah
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Porch
  • Wi-Fi
  • TV
  • Washer
  • Dryer
  • Grill
  • Deck
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
The Guest House (see #1289 for Main House)is approximately 1400SF and includes a Master Bed and Bath with a stand up glass enclosed shower. There is an additional bedroom and bathroom with a tub. A special feature is the state of the art kitchen as well as a great family room. There is an outside... View all property information
Make Enquiry
From
$5,813
Per Week
View Details
1 / 20
Menemsha
4 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • Stereo System
  • Dryer
  • VCR
  • TV
  • Washer
  • Satellite TV
  • Wi-Fi
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Welcome to Menemsha! Enjoy your stay in this country style four bedroom home with three full baths. First floor bedrooms include two with Queen beds and one bedroom with a full bed. The second floor bedroom is equipped with three twins for the children in your group. The linens are provided for you... View all property information
Make Enquiry
Enquire for rates
1 / 30
Chilmark
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Fax
  • Toaster
  • Satellite TV
  • Grill
  • DVD Player
  • TV
  • Internet Access
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Martha's Vineyard Local Experience:We are offering a unique week on Martha's VineyardFour Bedroom Home set on 5 acres of woods and meadow. A small farm setting with chickens and pigs and a garden for you to enjoy.Be a farmer for a week, without the work! Our hens lay eggs that you can collect every... View all property information
Make Enquiry
From
$9,882
Per Week
View Details
1 / 23
Chilmark
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Number Of Bedrooms
  • Internet Access
  • Dryer
  • Microwave
  • TV
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This historic farmhouse is quietly tucked away above Menemsha Pond with sweeping sunset and water views of The Pond and Menemsha Harbor. The tranquil setting is classic Chilmark with rolling hills and stonewalls, plus a private association beach just a short stroll away on Menemsha Pond.... View all property information
Make Enquiry
From
$9,301
Per Week
View Details
1 / 19
Aquinnah
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • VCR
  • Dryer
  • Fax
  • Patio
  • Dishwasher
  • TV
  • Deck
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Tucked away on an Aquinnah hillside with sweeping water views from Menemsha Harbor and Vineyard Sound to Quitsa and Menemsha Ponds, Hilltop House is designed around those views, and an equally inspiring pool compound with lush gardens and coastal-inspired pool house suite. Starting with a roof deck... View all property information
Make Enquiry
From
$4,069
Per Week
View Details
1 / 22
Aquinnah
4 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • Washer
  • Microwave
  • Patio
  • Fireplace
  • Dishwasher
  • DVD Player
  • Grill
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This contemporary farm house sits on five acres. Mature oaks provide privacy on three sides, views of Vineyard Sound grace the fourth. It is a short walk to Menemsha Pond, a shallow and warm swimming area for small children, and to Lobsterville Beach, an uncrowded expanse of sea shore for swimming... View all property information
Make Enquiry
From
$8,720
Per Week
View Details
1 / 27
Chilmark
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Fireplace
  • Grill
  • TV
  • Microwave
  • Satellite TV
  • Deck
  • Dryer
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Peaceful up-island setting on eight acres overlooking meadow and pond. The property borders 46 acres of conservation land in back, and approximately 25 acres in front. Open, bright, sun-filled living area with hardwood flooring throughout the home. Tastefully decorated and comfortably furnished.... View all property information
Make Enquiry
Enquire for rates
1 / 12
Aquinnah
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Internet Access
  • Air Conditioning
  • Satellite TV
  • Toaster
  • Grill
  • TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Down a private country road, this bright and breezy post & beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and the Gay Head cliffs. This very Vineyard house offers three levels with 2... View all property information
Make Enquiry
From
$3,488
Per Week
View Details
1 / 26
Aquinnah
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Stereo System
  • Fireplace
  • Dryer
  • Washer
  • Deck
  • Microwave
  • Satellite TV
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Very spacious five bedroom home located on four acres in Aquinnah. Approximately one mile from town beaches and the Gay Head Lighthouse. Larsen s Fish market and Menemsha Harbor are about five miles away by road or 1.5 as a crow flies. The Great Room has a two-story beach stone fireplace and a... View all property information
Make Enquiry
From
$2,907
Per Week
View Details
1 / 23
Chilmark
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dryer
  • TV
  • Grill
  • DVD Player
  • Satellite TV
  • Deck
  • Ceiling Fans
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming, remodeled in 2000, this is a seaside cottage overlooking Menemsha Harbor and beach. Bright and open interior with upscale details, the house is very comfortable. Master suite upstairs with deck and views of harbor, beach and sunsets. Backyard is private with outdoor deck and screened in... View all property information
Make Enquiry
From
$2,907
Per Week
View Details
1 / 16
Chilmark
4 Bedrooms, 4 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Dryer
  • TV
  • Washer
  • Deck
  • Ceiling Fans
  • Dishwasher
  • Grill
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Spacious, contemporary Cape-style home with a wrap around deck tucked into a wooded hilllside on 3.8 acres. Distant waterviews of Cape Higon and Vineyard Sound. The overall design and layout with the 4 bedrooms and 2 lofts allows space for extended family get-togethers and special occasions.... View all property information
Make Enquiry
From
$1,163
Per Week
View Details
1 / 14
Chilmark
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Fireplace
  • Deck
  • DVD Player
  • Dryer
  • Dishwasher
  • Washer
  • VCR
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This wonderful three bedroom up-island retreat, is the perfect summer vacation home, with lots of room to spread out. The master bedroom on the first floor offers great light in the morning sun with ensuite bathroom. The second floor with two bedrooms, shared bathroom and small office area on the... View all property information
Make Enquiry
From
$1,163
Per Week
View Details
1 / 17
Chilmark
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Grill
  • Washer
  • Dishwasher
  • Microwave
  • Dryer
  • Patio
  • Fireplace
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
What could be a more elegant, peaceful and romantic hideaway for a week than the Pond House? It sits at the conjunction of ocean and land, pond and meadow, with a view beyond dazzling outside and a warm fire in the fireplace inside. Gourmet kitchen. Antique and comfortable furniture. Quality... View all property information
Make Enquiry
From
$3,052
Per Week
View Details
1 / 25
Chilmark
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Deck
  • Microwave
  • Dishwasher
  • Grill
  • TV
  • Dryer
  • VCR
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Eighteenth century farm house with guest house on four acres. Secluded setting with stone walls, pond view and abundant wildlife. The perfect up-island getaway. Additional amenities include: coffee maker, smoke free, lobster pot, food processor, 1st floor bedroom, 1 king bed(s), vacuum cleaner,... View all property information
Make Enquiry
From
$8,720
Per Week
View Details
1 / 17
Chilmark
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Ceiling Fans
  • DVD Player
  • Washer
  • Microwave
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Breathtaking south shore ocean views from this pastoral setting await you. This striking contemporary has great spaces for everyone. Lovely furnishings and decor. All this and Chilmark beaches too. Additional amenities include: coffee maker, smoke free, lobster pot, 1st floor bedroom, 1 king... View all property information
Make Enquiry
From
$1,860
Per Week
View Details
1 / 14
Chilmark
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • TV
  • Toaster
  • Deck
  • VCR
  • DVD Player
  • Microwave
  • Stereo System
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kick back and relax in this beautiful one bedroom cottage overlooking Menemsha Harbor. Shop at the Menemsha General Store, fish from Dutcher Dock, and swim at Menemsha Beach, or enjoy a lobster dinner while watching sunset from the balcony of your upstairs living room. A little slice of heaven... View all property information
Make Enquiry
From
$11,626
Per Week
View Details
1 / 20
Chilmark
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • VCR
  • Waterfront
  • Dryer
  • Satellite TV
  • Linens Provided
  • Deck
  • TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Wonderful four bedroom home directly on Quitsa Pond with private deep water dock. One bedroom guest cottage included in rental. Additional amenities include: dock/boat-slip, smoke free, pets considered, lobster pot, 1st floor bedroom, 1 king bed(s), 8 dining capacity, 1 double bed(s), 4 single... View all property information
Make Enquiry
From
$5,813
Per Week
View Details
1 / 19
Chilmark
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • TV
  • Washer
  • Satellite TV
  • Dryer
  • VCR
  • Microwave
  • Fireplace
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Wonderful Vineyard cape situated on one of the most gorgeous spots on the island. The views are phenomenal in any direction and the house is cozy and charming. Large stretch of gorgeous, sandy and private beach. One of the most breathtaking spots on the island! Additional amenities include:... View all property information
Make Enquiry
Go to map view
Book Online(9)
Use filters to find the best results!

Suitability

  • Wheelchair access (1)
  • Elder access (2)
  • Suitable for children (0)
  • Pet friendly (15)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (231)
  • Internet (226)
  • Grill (220)
  • Washer/Dryer (138)
  • Air Conditioning (76)
  • 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
Nearby cities