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

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chilmark vacation homes

Pool

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 ￥38,009
￥83,649 total
includes taxes & fees
Jul 15 - Jul 16
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fridge, microwave, oven, stovetop

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 ￥88,957
￥186,963 total
includes taxes & fees
Jul 22 - Jul 23
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Terrace/patio

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 ￥48,765
￥62,240 total
includes taxes & fees
Jul 5 - Jul 6
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Exterior

Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (7 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is ￥67,915
￥152,327 total
includes taxes & fees
Jun 29 - Jun 30
Elisa's Cottage - Your Family Vacation Destination
Beach

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 ￥69,548
￥143,646 total
includes taxes & fees
Jul 19 - Jul 20
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Interior

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 ￥55,477
￥119,026 total
includes taxes & fees
Jun 30 - Jul 1
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Property grounds

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 ￥117,262
￥219,326 total
includes taxes & fees
Jul 26 - Jul 27
Chappy - Family Beach House
Beach nearby

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 ￥125,349
￥236,020 total
includes taxes & fees
Jul 3 - Jul 4
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Exterior

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 ￥68,416
￥151,397 total
includes taxes & fees
Jul 11 - Jul 12
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
Dining

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 ￥145,566
￥285,448 total
includes taxes & fees
Jul 26 - Jul 27
4-bedroom house in lovely Edgartown..Centrally located
Interior

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

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 ￥218,349
￥348,500 total
includes taxes & fees
Jul 9 - Jul 10
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
TV, fireplace, books

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 ￥218,349
￥350,848 total
includes taxes & fees
Jul 5 - Jul 6
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Smart TV, DVD player

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 ￥137,479
￥214,087 total
includes taxes & fees
Jul 29 - Jul 30
The Seashell Cove - Martha's Vineyard
Beach nearby

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

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 ￥323,480
￥513,085 total
includes taxes & fees
Jun 29 - Jun 30
Beautiful Estate with salt water pool & pond with kayaks
Outdoor dining

Water Views, Walk to Fairmount Heights Beach

Water Views, Walk to Fairmount Heights Beach
Falmouth Heights
The price is ￥96,685
￥192,291 total
includes taxes & fees
Jun 29 - Jun 30
Water Views, Walk to Fairmount Heights Beach
Exterior

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 ￥202,175
￥288,881 total
includes taxes & fees
Jul 12 - Jul 13
The Costal Corner - Martha's Vineyard
Outdoor pool

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.
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

ShoreWay Acres Inn & Cape Cod Lodging

ShoreWay Acres Inn & Cape Cod Lodging

8/10 Good
"Perfect spot if you like to be close to downtown. Easy walking to restaurant and shops. Staff were great. Room was comfortable. Only improvement I would suggest is more outlets and in accessible locations in the room."
Rev Shirley 2-night trip
Posted 8 hours ago
ShoreWay Acres Inn & Cape Cod Lodging

Find out more about Chilmark

Chilmark Vacation Homes information

Number of reviews
10,819
Accommodation
927 Vacation Homes
Lowest Price
￥24,982
Highest Price
￥110,484