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 $1,767
CA $3,059 total
includes taxes & fees
Aug 3 - Aug 4
NEW Construction: a Love Letter to Martha's Vineyard

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 $593
CA $1,291 total
includes taxes & fees
Jul 25 - Jul 26
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

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 $946
CA $1,834 total
includes taxes & fees
Jul 30 - Jul 31
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 $883
CA $2,022 total
includes taxes & fees
Jul 19 - Jul 20
4-bedroom house in lovely Edgartown..Centrally located

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 $725 total
includes taxes & fees
Jul 27 - Jul 28
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

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 $1,893
CA $3,128 total
includes taxes & fees
Jul 19 - Jul 20
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is CA $1,115
CA $2,049 total
includes taxes & fees
Aug 17 - Aug 18
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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 $1,430
CA $2,915 total
includes taxes & fees
Jul 27 - Jul 28
New 4 BR house near center and beaches with bikes

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 $1,136
CA $1,807 total
includes taxes & fees
Jul 19 - Jul 20
The Seashell Cove - Martha's Vineyard

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"I was able to get to the house within minutes from the Vineyard Haven ferry. There was plenty of parking. The house was immaculate and well appointed. The beaches and restaurants nearby were great. It was also very convenient to find on the way back from a long day. The beds are very comfortable."
United States
Ross
The price is CA $733
CA $1,350 total
includes taxes & fees
Jul 24 - Jul 25
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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 $3,786
CA $5,709 total
includes taxes & fees
Jul 19 - Jul 20
Beautiful Estate with salt water pool & pond with kayaks

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 $1,017
CA $1,917 total
includes taxes & fees
Jul 26 - Jul 27
Chappy - Family Beach House

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 $1,343
CA $2,909 total
includes taxes & fees
Jul 26 - Jul 27
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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 $931
CA $1,767 total
includes taxes & fees
Aug 5 - Aug 6
Elisa's Cottage - Your Family Vacation Destination

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, (16 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is CA $771
CA $1,650 total
includes taxes & fees
Jul 22 - Jul 23
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

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 $1,262
CA $2,566 total
includes taxes & fees
Jul 30 - Jul 31
Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill

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 $1,087
CA $2,019 total
includes taxes & fees
Jul 31 - Aug 1
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

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 $855
CA $1,622 total
includes taxes & fees
Aug 10 - Aug 11
Spring Escape in Hatchville – Sleeps 6 + Dogs!

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette
Fairhaven
8.4 out of 10, Very good, (5 reviews)
"The home was beautiful and well equipped. Perfect location in a quiet new england neighborhood. My family enjoyed our stay!"
United States
lea m.
The price is CA $1,080
CA $1,825 total
includes taxes & fees
Aug 4 - Aug 5
World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

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 $1,324
CA $2,463 total
includes taxes & fees
Jul 24 - Jul 25
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
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
216
Accommodation
895 Vacation Homes
Lowest Price
CA $725
Highest Price
CA $5,709

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