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12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Vacation Homes in Chilmark

On the beach, sun loungers, beach towels
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Dartmouth
10.0 out of 10, Exceptional, (17)
"Property ideal for our needs of visiting family and meeting our first grandchild "
United States
Carol M.
The price is AED 496
AED 1,321 total
includes taxes & fees
3 Dec - 4 Dec
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
Fridge, microwave, oven, stovetop
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, (209)
"We had a great stay. House is spacious, clean and well-stocked with everything we needed. We loved that we were able to walk to downtown shops and restaurants, the ferry to Martha’s Vineyard and the beach. Would definitely stay here again. "
United States
Ava B.
The price is AED 595
AED 1,824 total
includes taxes & fees
2 Dec - 3 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Beach nearby, beach towels
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport
9.8 out of 10, Exceptional, (22)
"Beautiful house! Had a wonderful time!"
United States
RYAN S.
The price is AED 646
AED 1,708 total
includes taxes & fees
3 Dec - 4 Dec
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
Outdoor dining
Newly Renovated Martha's Vineyard Vacation Rental!

Newly Renovated Martha's Vineyard Vacation Rental!

Katama
9.6 out of 10, Exceptional, (47)
"Stay was nice, property is very clean and in close distance to most everything. Just wish they had made the lack of towels and linens more obvious in the listing. "
United States
James L.
The price is AED 697
AED 2,227 total
includes taxes & fees
2 Dec - 3 Dec
Newly Renovated Martha's Vineyard Vacation Rental!
Game room
Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth
10.0 out of 10, Exceptional, (11)
"The house is very nice and clean and Brian was extremely communicative and flexible with a late checkout. Would definitely stay again"
United States
Michael B.
The price is AED 1,058
AED 2,682 total
includes taxes & fees
2 Dec - 3 Dec
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Terrace/patio
The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is AED 918
AED 2,109 total
includes taxes & fees
8 Dec - 9 Dec
The Seashell Cove - Martha's Vineyard
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.

East Falmouth
10.0 out of 10, Exceptional, (88)
"Great stay! "
United States
Michael M.
The price is AED 1,074
AED 3,281 total
includes taxes & fees
8 Dec - 9 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Fridge, microwave, oven, stovetop
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)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is AED 1,836
AED 3,984 total
includes taxes & fees
23 Dec - 24 Dec
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs
9.4 out of 10, Exceptional, (3)
"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 1,286
AED 3,282 total
includes taxes & fees
2 Dec - 3 Dec
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Fridge, microwave, oven, stovetop
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

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

Mashpee
10.0 out of 10, Exceptional, (8)
"Nice house! Great area. Close to nice beach !"
United States
Cally G.
The price is AED 2,567
AED 4,527 total
includes taxes & fees
1 Jan - 2 January 2026
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
4 bedrooms, desk, iron/ironing board, travel crib
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, (13)
"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 3,185
AED 5,453 total
includes taxes & fees
29 Dec - 30 Dec
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"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 2,020
AED 4,349 total
includes taxes & fees
2 Dec - 3 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Outdoor dining
Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!

2.5 star property
Falmouth
The price is AED 2,231
AED 5,311 total
includes taxes & fees
2 Dec - 3 Dec
Cape Cod Escape at Casa de Leo!
Terrace/patio
Stones Throw Waterfront

Stones Throw Waterfront

Dartmouth
8.8 out of 10, Excellent, (6)
"Great property very close to shops and restaurants in Padanaram. Very clean with lots of kitchen amenities. The portable AC units worked perfectly throughout the heatwave during our stay. Very quiet and peaceful location. We used the paddle boards and kayaks which was a nice bonus. It’s tricky getting them in the water especially at low tide."
United States
Becky S.
The price is AED 1,306
AED 2,369 total
includes taxes & fees
2 Dec - 3 Dec
Stones Throw Waterfront
Exterior
Cape cod getaway Close to Old Silver

Cape cod getaway Close to Old Silver

Falmouth
The price is AED 1,469
AED 1,921 total
includes taxes & fees
8 Dec - 9 Dec
Cape cod getaway Close to Old Silver
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

The Coonamessett

The Coonamessett

10/10 Excellent
"Staff was fantastic. The food was plentiful and delicious. Our room was big, bright, and clean."
Susan 1-night trip
Posted 3 days ago
The Coonamessett