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

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Our top choices for Chilmark vacation homes

NEW Construction: a Love Letter to Martha's Vineyard

NEW Construction: a Love Letter to Martha's Vineyard
West Tisbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay at this home in West Tisbury. The house was exactly as described - comfortable, clean, well-appointed, and thoughtfully stocked with everything we needed. The location was perfect for exploring the island while still feeling peaceful and relaxing. Jack was incredibly responsive, helpful, and easy to communicate with throughout our stay. We truly felt at home and would gladly stay here again. Highly recommend!"
United States
Nini D.
The price is CA $2,038
CA $3,413 total
includes taxes & fees
Aug 3 - Aug 4
NEW Construction: a Love Letter to Martha's Vineyard

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 $333
CA $732 total
includes taxes & fees
Jul 15 - Jul 16
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is CA $892
CA $2,041 total
includes taxes & fees
Jul 26 - Jul 27
4-bedroom house in lovely Edgartown..Centrally located

Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.6 out of 10, Excellent, (7 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is CA $468
CA $1,363 total
includes taxes & fees
Jul 26 - Jul 27
Cozy Cottage walk to Menauhant Beach

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

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.6 out of 10, Exceptional, (14 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is CA $778
CA $1,665 total
includes taxes & fees
Jul 23 - Jul 24
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $466
CA $1,137 total
includes taxes & fees
Jul 15 - Jul 16
Backyard Retreat / 5 Min > Beach & Main St

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 $599
CA $1,325 total
includes taxes & fees
Jul 12 - Jul 13
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
The price is CA $1,026
CA $1,930 total
includes taxes & fees
Jul 26 - Jul 27
Chappy - Family Beach House

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is CA $778
CA $1,502 total
includes taxes & fees
Aug 2 - Aug 3
Spring Escape in Hatchville – Sleeps 6 + Dogs!

Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is CA $905
CA $1,739 total
includes taxes & fees
Aug 5 - Aug 6
Elisa's Cottage - Your Family Vacation Destination

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 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 $956
CA $1,853 total
includes taxes & fees
Jul 30 - Jul 31
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (9 reviews)
"Great place"
United States
Aaron Q.
The price is CA $1,273
CA $2,127 total
includes taxes & fees
Jul 14 - Jul 15
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

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 $977
CA $1,752 total
includes taxes & fees
Jul 14 - Jul 15
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

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, (49 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 $1,098
CA $2,071 total
includes taxes & fees
Jul 31 - Aug 1
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $1,397
CA $2,813 total
includes taxes & fees
Jul 13 - Jul 14
New 4 BR house near center and beaches with bikes

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, (16 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 $1,969
CA $3,055 total
includes taxes & fees
Jul 28 - Jul 29
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill

Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill
Falmouth
The price is CA $1,275
CA $2,593 total
includes taxes & fees
Jul 30 - Jul 31
Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill

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 $1,911
CA $3,160 total
includes taxes & fees
Jul 20 - Jul 21
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Stay was awesome! Perfect house for family gatherings "
United States
Diana P.
The price is CA $940
CA $2,209 total
includes taxes & fees
Aug 1 - Aug 2
Recently renovated 3 bedroom

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 $1,204
CA $1,887 total
includes taxes & fees
Jul 29 - Jul 30
The Seashell Cove - Martha's Vineyard
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
203
Accommodation
895 Vacation Homes
Lowest Price
CA $732
Highest Price
CA $3,160

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