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Our top choices for Chilmark vacation homes

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living areaFalmouth
10.0 out of 10, Exceptional, (8)
$514 nightly
The price is $588
Jan 16 - Jan 17, 2026
Total with taxes and fees

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to BeachNew Seabury
10.0 out of 10, Exceptional, (8)
$812 nightly
The price is $929
Dec 20 - Dec 21
Total with taxes and fees

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)
$1,085 nightly
The price is $1,212
Dec 20 - Dec 21
Total with taxes and fees

The Seashell Cove - Martha's Vineyard
The Seashell Cove - Martha's VineyardKatama
9.8 out of 10, Exceptional, (24)
$486 nightly
The price is $543
Dec 22 - Dec 23
Total with taxes and fees

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)
$800 nightly
The price is $894
Dec 20 - Dec 21
Total with taxes and fees

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)
$829 nightly
The price is $948
Dec 20 - Dec 21
Total with taxes and fees

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 BeachFalmouth
10.0 out of 10, Exceptional, (211)
$432 nightly
The price is $494
Dec 21 - Dec 22
Total with taxes and fees

Newly Renovated Martha's Vineyard Vacation Rental!
Newly Renovated Martha's Vineyard Vacation Rental!Katama
9.6 out of 10, Exceptional, (47)
$558 nightly
The price is $623
Dec 30 - Dec 31
Total with taxes and fees
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.
Top Chilmark Hotel Reviews

The Coonamessett
10/10 Excellent
Find out more about Chilmark
Chilmark Vacation Homes information
Number of reviews | 396 |
|---|---|
Accommodation | 887 Vacation Homes |
Lowest Price | $437 |
Highest Price | $1,722 |
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