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

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $1,395
CA $2,349 total
includes taxes & fees
Aug 2 - Aug 3
Walk to Beach! Oak Bluffs Home & Studio

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 $330
CA $727 total
includes taxes & fees
Jul 28 - Jul 29
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 $886
CA $2,028 total
includes taxes & fees
Jul 28 - Jul 29
4-bedroom house in lovely Edgartown..Centrally located

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 $1,264
CA $2,113 total
includes taxes & fees
Jul 16 - Jul 17
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

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

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (15 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is CA $773
CA $1,654 total
includes taxes & fees
Jul 22 - Jul 23
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 $550
CA $1,244 total
includes taxes & fees
Jul 16 - Jul 17
Backyard Retreat / 5 Min > Beach & Main St

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 $1,935 total
includes taxes & fees
Jul 26 - Jul 27
Chappy - Family Beach House

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 $949
CA $1,839 total
includes taxes & fees
Jul 16 - Jul 17
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 $1,090
CA $2,024 total
includes taxes & fees
Jul 31 - Aug 1
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

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! ☀️ 🏖

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is CA $1,347
CA $2,924 total
includes taxes & fees
Jul 16 - Jul 17
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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!

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 $933
CA $2,178 total
includes taxes & fees
Aug 1 - Aug 2
Recently renovated 3 bedroom

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 $1,898
CA $3,136 total
includes taxes & fees
Jul 16 - Jul 17
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is CA $778
CA $1,528 total
includes taxes & fees
Aug 2 - Aug 3
Spring Escape in Hatchville – Sleeps 6 + Dogs!

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 $595
CA $1,316 total
includes taxes & fees
Jul 28 - Jul 29
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

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 $919
CA $1,753 total
includes taxes & fees
Aug 5 - Aug 6
Elisa's Cottage - Your Family Vacation Destination

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)
"This property is amazing. One of the most thoughtful hosts I have ever had with VRBO. First class all the way. Great location. The view is outstanding. Just a wonderful stay, the kitchen is a dream. Just a fantastic find and I cant wait to return to No Egrets Haven. "
United States
Valerie J.
The price is CA $1,956
CA $3,034 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 $1,274
CA $2,590 total
includes taxes & fees
Jul 30 - Jul 31
Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill
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
193
Accommodation
895 Vacation Homes
Lowest Price
CA $727
Highest Price
CA $3,139

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