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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

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 AED 863
AED 1,900 total
includes taxes & fees
15 Jul - 16 Jul
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
9.6 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 AED 1,451
AED 3,540 total
includes taxes & fees
7 Jul - 8 Jul
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Interior

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is AED 1,250
AED 3,001 total
includes taxes & fees
6 Jul - 7 Jul
Backyard Retreat / 5 Min > Beach & Main St
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 AED 1,396
AED 3,006 total
includes taxes & fees
19 Jul - 20 Jul
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
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
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
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 AED 2,479
AED 4,804 total
includes taxes & fees
30 Jul - 31 Jul
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Marina

Vineyard Haven Family Beach, Fire Pit & Garden View

Vineyard Haven Family Beach, Fire Pit & Garden View
Tisbury
10.0 out of 10, Exceptional, (2 reviews)
"House was wonderful - the kitchen was very nicely stocked and the beds were very comfortable."
United States
Jane H.
Vineyard Haven Family Beach, Fire Pit & Garden View
Property grounds

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 AED 2,663
AED 5,038 total
includes taxes & fees
26 Jul - 27 Jul
Chappy - Family Beach House
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
The price is AED 2,534
AED 4,542 total
includes taxes & fees
14 Jul - 15 Jul
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!
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, (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 AED 2,847
AED 5,339 total
includes taxes & fees
31 Jul - 1 Aug
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Terrace/patio

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 AED 2,020
AED 3,931 total
includes taxes & fees
2 Aug - 3 Aug
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Property grounds

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)
The price is AED 3,596
AED 7,471 total
includes taxes & fees
7 Jul - 8 Jul
New 4 BR house near center and beaches with bikes
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 AED 3,223
AED 5,053 total
includes taxes & fees
9 Jul - 10 Jul
The Seashell Cove - Martha's Vineyard
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 AED 2,571
AED 5,625 total
includes taxes & fees
20 Jul - 21 Jul
4-bedroom house in lovely Edgartown..Centrally located
Outdoor dining

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, (8 reviews)
"Great place"
United States
Aaron Q.
The price is AED 3,302
AED 5,520 total
includes taxes & fees
14 Jul - 15 Jul
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Terrace/patio

Pool Escape in East Falmouth

Pool Escape in East Falmouth
East Falmouth
The price is AED 2,340
AED 5,709 total
includes taxes & fees
24 Jul - 25 Jul
Pool Escape in East Falmouth
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 AED 4,959
AED 8,201 total
includes taxes & fees
9 Jul - 10 Jul
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Smart TV, books

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 AED 5,109
AED 7,844 total
includes taxes & fees
28 Jul - 29 Jul
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Private kitchen

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 AED 3,302
AED 5,486 total
includes taxes & fees
6 Jul - 7 Jul
Charming Vineyard Classic Home, Walk to Town & Boat
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.
The price is AED 3,468
AED 6,453 total
includes taxes & fees
24 Jul - 25 Jul
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

8/10 Good
"This was my second stay! I love the great location, private beach and friendly hotel staff! There are excellent restaurants and FREE public transportation STEPS away. A cruise ships was docked a few feet away from their beach. While lying on their private beach, I discovered a Horseshoe crab in the sand, which I've never seen before. I did have an issue with the AC in my unit this trip. We didnt have it on automatic, nor a timer. However, it kept shutting off itself, and the room had gotten hot quickly before it came back on. Since we were out all day into evenings, and staff leaves at night, we didnt inform them. Overall, I definitely will stay here again!"
Ann Beth 3-night trip
Posted 5 hours ago
Vineyard Harbor Motel - Private Beach

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