A dock with boats, a small wooden structure, and a forested shoreline.

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Our top choices for Chilmark vacation homes

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is CA $334
CA $734 total
includes taxes & fees
Jul 15 - Jul 16
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Westport
9.6 out of 10, Exceptional, (45 reviews)
"Super quiet and private neighborhood which makes for great walks!"
United States
Caitlin J.
The price is CA $428
CA $546 total
includes taxes & fees
Jul 5 - Jul 6
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (13 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is CA $561
CA $1,361 total
includes taxes & fees
Jul 7 - Jul 8
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (218 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
The price is CA $487
CA $1,045 total
includes taxes & fees
Jul 1 - Jul 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is CA $600
CA $1,329 total
includes taxes & fees
Jul 11 - Jul 12
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (14 reviews)
"This is a beautiful and unique home with plenty of space and activities for the family. The photos were accurate and there was so much space for everyone to relax. We enjoyed our stay so much. "
United States
Lisa F.
The price is CA $539
CA $1,168 total
includes taxes & fees
Jul 19 - Jul 20
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.6 out of 10, Exceptional, (48 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is CA $1,101
CA $2,089 total
includes taxes & fees
Jul 3 - Jul 4
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
10.0 out of 10, Exceptional, (15 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
The price is CA $1,029
CA $1,947 total
includes taxes & fees
Jul 26 - Jul 27
Chappy - Family Beach House

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (1 review)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
The price is CA $994
CA $2,174 total
includes taxes & fees
Jul 27 - Jul 28
4-bedroom house in lovely Edgartown..Centrally located

Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!
Katama
The price is CA $979
CA $1,757 total
includes taxes & fees
Jul 15 - Jul 16
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is CA $1,916
CA $3,170 total
includes taxes & fees
Jul 19 - Jul 20
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is CA $1,207
CA $1,904 total
includes taxes & fees
Jul 29 - Jul 30
The Seashell Cove - Martha's Vineyard

Charming Vineyard Classic Home, Walk to Town & Boat

Charming Vineyard Classic Home, Walk to Town & Boat
Vineyard Haven
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay thank you "
United States
Joseph S.
The price is CA $1,276
CA $2,079 total
includes taxes & fees
Jul 6 - Jul 7
Charming Vineyard Classic Home, Walk to Town & Boat

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.2 out of 10, Wonderful, (5 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is CA $1,065
CA $1,950 total
includes taxes & fees
Jul 30 - Jul 31
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Dartmouth
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
The price is CA $2,126
CA $3,257 total
includes taxes & fees
Jul 28 - Jul 29
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is CA $4,259
CA $6,158 total
includes taxes & fees
Jul 19 - Jul 20
Beautiful Estate with salt water pool & pond with kayaks

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
Falmouth
9.6 out of 10, Exceptional, (22 reviews)
"Very clean place in a great location for a Falmouth getaway. Our host was very responsive and accommodating. "
United States
Jimmy C.
The price is CA $1,340
CA $2,494 total
includes taxes & fees
Jul 24 - Jul 25
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

The Costal Corner - Martha's Vineyard

The Costal Corner - Martha's Vineyard
Katama
10.0 out of 10, Exceptional, (6 reviews)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
United States
stephen t.
The price is CA $1,774
CA $2,527 total
includes taxes & fees
Jul 12 - Jul 13
The Costal Corner - Martha's Vineyard

Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!

Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!
Falmouth
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful home in a great area!"
United States
Jillian P.
The price is CA $2,839
CA $4,146 total
includes taxes & fees
Jul 25 - Jul 26
Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chilmark Hotel Reviews

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Chilmark Vacation Homes information

Number of reviews
285
Accommodation
895 Vacation Homes
Lowest Price
CA $546
Highest Price
CA $6,158

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