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Search results showing properties in Chilmark, Massachusetts, United States of America

Google map showing 500 properties

Premier Host
House · 3 min drive to the beach

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

Sleeps 3 · 2 bedrooms · 1 bathroom
Private host
10 out of 10
exceptional
(35 reviews)
Unavailable
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Premier Host
House · 6 min drive to the beach

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Sleeps 4 · 2 bedrooms · 1 bathroom
10 out of 10
exceptional
(2 reviews)
Unavailable
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House · 3 min walk to Menemsha Beach

Menemsha Harborside Cottage

Sleeps 4 · 2 bedrooms · 1 bathroom
10 out of 10
exceptional
(5 reviews)
Unavailable
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House · 11 min drive to the beach

Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday

Sleeps 6 · 3 bedrooms
9.8 out of 10
exceptional
(15 reviews)
Unavailable
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House · 6 min walk to Menemsha Beach

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Sleeps 6 · 3 bedrooms · 1 bathroom
Unavailable
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House · 7 min drive to the beach

Private Hillside Home with Open Property and a Fully Equipped Kitchen

Sleeps 8 · 4 bedrooms · 4 bathrooms
9.6 out of 10
exceptional
(7 reviews)
Unavailable
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House · 8 min drive to the beach

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

Sleeps 10 · 5 bedrooms · 3+ bathrooms
Private host
10 out of 10
exceptional
(19 reviews)
Unavailable
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House · 7 min drive to the beach

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Sleeps 8 · 4 bedrooms · 2 bathrooms
8.4 out of 10
very good
(18 reviews)
Unavailable
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House · 3.3 mi (5.4 km) to Chilmark centre

Beautiful dog-friendly home with water view, balcony & washer/dryer

Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.4 out of 10
exceptional
(8 reviews)
Unavailable
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House · 5 min drive to the beach

Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby

Sleeps 6 · 3 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(13 reviews)
Unavailable
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Cottage · 11 min drive to the beach

Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach

Sleeps 4 · 2 bedrooms · 1+ bathroom
Private host
10 out of 10
exceptional
(14 reviews)
Unavailable
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House · 4 min drive to the beach

Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice

Sleeps 8 · 4 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(37 reviews)
Unavailable
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House · 3.2 mi (5.1 km) to Chilmark centre

Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!

Sleeps 8 · 4 bedrooms · 2+ bathrooms
Private host
10 out of 10
exceptional
(3 reviews)
Unavailable
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House · 3.5 mi (5.7 km) to Chilmark centre

Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D

Sleeps 8 · 4 bedrooms · 2 bathrooms
7.8 out of 10
good
(11 reviews)
Unavailable
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Cottage · 8 min drive to the beach

Charming Rustic Cottage

Sleeps 5 · 2 bedrooms · 1+ bathroom
Private host
10 out of 10
exceptional
(8 reviews)
Unavailable
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House · 3 min drive to the beach

Spectacular Newly Renovated Home in Menemsha

Sleeps 10 · 3 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(24 reviews)
Unavailable
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House · 9 min drive to the beach

Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views

Sleeps 8 · 4 bedrooms · 3 bathrooms
Private host
10 out of 10
exceptional
(9 reviews)
Unavailable
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House · 3.2 mi (5.1 km) to Chilmark centre

Private guesthouse in Peaceful Chilmark Neigborhood

Sleeps 4 · 2 bedrooms · 1 bathroom
Private host
10 out of 10
exceptional
(2 reviews)
Unavailable
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