Chilmark, Massachusetts

Vacation Rentals in Chilmark, Massachusetts

Discover 26 vacation rental properties in Chilmark. From 1 to 5 bedrooms. Average $603/night. 100% have pools.

26 verified listings Book securely on VRBO Prices updated March 2026

26 properties available

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

1 bed 1 bath
PoolA/CWiFiBalcony
$318/night
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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

2 beds 2 baths
PoolA/CWiFiBalcony
$395/night
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Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

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

2 beds 1 bath
PoolA/CWiFiBalcony
$489/night
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Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

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

2 beds 1 bath
PoolA/CWiFiBalcony
$273/night
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Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

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

3 beds 1 bath
PoolA/CWiFiBalcony
$599/night
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Menemsha Harborside Cottage. Reduced price for week 7/18-7/25.

Menemsha Harborside Cottage. Reduced price for week 7/18-7/25.

2 beds 1 bath
PoolA/CWiFiBalcony
$320/night
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Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

5 beds 3 baths
PoolA/CWiFiBalcony
$1,717/night
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Private Hillside Home with Open Property and a Fully Equipped Kitchen

Private Hillside Home with Open Property and a Fully Equipped Kitchen

4 beds 4 baths
PoolA/CWiFiBalcony
$443/night
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice

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

4 beds 2 baths
PoolA/CWiFiBalcony
$751/night
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Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday

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

3 beds
PoolA/CWiFiBalcony
$526/night
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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

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

4 beds 2 baths
PoolA/CWiFiBalcony
$685/night
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Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach

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

2 beds 1 bath
PoolA/CWiFiBalcony
$376/night
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Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby

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

3 beds 2 baths
PoolA/CWiFiBalcony
$424/night
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Beautiful dog-friendly home with water view, balcony & washer/dryer

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

4 beds 2 baths
PoolA/CWiFiBalcony
$296/night
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Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D

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

4 beds 2 baths
PoolA/CWiFiBalcony
$592/night
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Charming Rustic Cottage

Charming Rustic Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$400/night
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Spectacular Newly Renovated Home in Menemsha

Spectacular Newly Renovated Home in Menemsha

3 beds 2 baths
PoolA/CWiFiBalcony
$766/night
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Menemsha Village - Davis Cottage - SSA boat reserv. available for some weeks.

Menemsha Village - Davis Cottage - SSA boat reserv. available for some weeks.

1 bed 1 bath
PoolA/CWiFiBalcony
$258/night
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Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!

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

4 beds 2 baths
PoolA/CWiFiBalcony
$894/night
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Chilmark pond side cottage with beach access, sweeping views 15 June - 15 Sept

Chilmark pond side cottage with beach access, sweeping views 15 June - 15 Sept

3 beds 2 baths
PoolA/CWiFiBalcony
$544/night
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Fully Appointed Water View House Ten Minutes Walk from Beach

Fully Appointed Water View House Ten Minutes Walk from Beach

4 beds 3 baths
PoolA/CWiFiBalcony
$1,201/night
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Best deal in Chilmark (Open Memorial Day weekend-Nov. 15)

Best deal in Chilmark (Open Memorial Day weekend-Nov. 15)

4 beds 3 baths
PoolA/CWiFiBalcony
$315/night
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Chilmark two bedroom, one bath cottage with waterfront and private beach

Chilmark two bedroom, one bath cottage with waterfront and private beach

2 beds 1 bath
PoolA/CWiFiBalcony
$888/night
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Private guesthouse in Peaceful Chilmark Neigborhood

Private guesthouse in Peaceful Chilmark Neigborhood

2 beds 1 bath
PoolA/CWiFiBalcony
$329/night
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Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views

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

4 beds 3 baths
PoolA/CWiFiBalcony
$871/night
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House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.

House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.

4 beds 2 baths
PoolA/CWiFiBalcony
$1,002/night
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