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Compare 663 Vacation Homes in Chilmark with updated reviews, rates, and availability.
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
9.8 out of 10, Exceptional, (9)
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.0 out of 10, (19)
Maushop Property - First Time Available
Maushop Property - First Time Available
10.0 out of 10, Exceptional, (23)
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Adorable waterfront home w/ boat access & a three-season sunroom
Adorable waterfront home w/ boat access & a three-season sunroom
9.2 out of 10, Wonderful, (15)
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
9.6 out of 10, Exceptional, (19)
Boating, Beach, Sunsets and fun for all
Boating, Beach, Sunsets and fun for all
9.8 out of 10, Exceptional, (18)
Private cottage nestled in center of island, access to Lambert's Cove beach
Private cottage nestled in center of island, access to Lambert's Cove beach
10.0 out of 10, Exceptional, (27)
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
10.0 out of 10, Exceptional, (2)
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
9.0 out of 10, Wonderful, (37)
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (158)
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very Good, (24)
Stunning East Falmouth Home w/ Pool and Central AC RPAM038
Stunning East Falmouth Home w/ Pool and Central AC RPAM038
10.0 out of 10, Exceptional, (7)
First Time Available to Rent in 40 Years
First Time Available to Rent in 40 Years
9.4 out of 10, Exceptional, (25)
Walk your way into Vineyard Haven from Walker Way!
Walk your way into Vineyard Haven from Walker Way!
10.0 out of 10, Exceptional, (33)
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
10.0 out of 10, Exceptional, (2)
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.
Other property types in Chilmark
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very Good, (18)
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (36)
Beautiful dog-friendly home with water view, balcony & washer/dryer
Beautiful dog-friendly home with water view, balcony & washer/dryer
9.4 out of 10, Exceptional, (8)
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.
Recent reviews of Chilmark hotelsExpedia verified reviews
5/5 Excellent
"Beautiful location with all amenities !"
A verified traveler from ames stayed at The Club at New Seabury
Posted 2 days ago
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