Home Vacation Rentals By Owner In Chilmark, MA

Showing 20 Of 93 Vacation Rentals
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Exceptional(76)

$678.39

/ Nightly
Private Vacation Home

Beachfront Aquinnah home. Beautiful views!

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$16314.54

/ Nightly
Private Vacation Home

Oceanfront Home w Private Beach!

Chilmark, Massachusetts, United States

Bed 6

Bed

Bath 5

Bath

Sleep 10

Sleeps
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Exceptional(7)

$886.34

/ Nightly
Cottage

Chilmark pond side cottage with beach access, sweeping views

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(65)

$469.89

/ Nightly
Private Vacation Home

Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.

Chilmark, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(13)

$1287.34

/ Nightly
Private Vacation Home

Luxury Home in Exclusive Aquinnah

Aquinnah, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(1)

$3063.37

/ Nightly
Private Vacation Home

Stunning private family home - spectacular sunsets

Chilmark, Massachusetts, United States

Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(2)

$336.22

/ Nightly
Private Vacation Home

Light and airy modern holiday cottage with access to private beach

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(28)

$567.28

/ Nightly
Private Vacation Home

Vintage 1920s House W/Beach Path & Glorious Sunset Water Views

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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$529.46

/ Nightly
Cottage

Classic Vineyard Summer Cottage; Private Waterfront Access; Menemsha Pond Views.

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$1497.9

/ Nightly
Private Vacation Home

Aquinnah Home by Lobsterville Beach w/ Ocean Views

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(1)

$1159.64

/ Nightly
Cottage

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

Chilmark, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(64)

$544.54

/ Nightly
Private Vacation Home

Custom-Built Aquinnah Escape—Walk to Menemsha Pond. Private Ocean Access. Kayaks

Aquinnah, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(29)

$427.33

/ Nightly
Cottage

Menemsha - Davis House

Chilmark, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(14)

$1063.83

/ Nightly
Private Vacation Home

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

Chilmark, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(4)

$479.86

/ Nightly
Private Vacation Home

Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(34)

$585.95

/ Nightly
Private Vacation Home

Modern beach house - Walking distance to Philbin Beach

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(5)

$471.82

/ Nightly
Private Vacation Home

Menemsha Village - Sunset House

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(10)

$472.01

/ Nightly
Cottage

Charming Rustic Cottage

Chilmark, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(31)

$797.38

/ Nightly
Private Vacation Home

Ocean Views: Every Room - Walk to Ocean Beach, Dog Friendly

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(30)

$552.92

/ Nightly
Private Vacation Home

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

Chilmark, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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View 79 Private vacation home

Home Most popular vacation rentals in Chilmark

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Exceptional(30)

$844.22

/ Nightly
Private vacation home

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

Chilmark, Massachusetts, United States

Bed 0

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(30)

$788.52

/ Nightly
Private vacation home

New Rates! Ocean Views! Lovely Secluded Home, Short Walk To Spectacular Beach!

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(30)

$794.35

/ Nightly
Private vacation home

Exceptional home w/ AC, modern amenities, private & peaceful, walk to beach.

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(30)

$797.38

/ Nightly
Private vacation home

Ocean Views: Every Room - Walk to Ocean Beach, Dog Friendly

Aquinnah, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(30)

$803.76

/ Nightly
Private vacation home

Pet-Friendly Historic Chilmark House

Chilmark, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(30)

$829.38

/ Nightly
Private vacation home

Open July 20-27th w/RT Ferry! 4 BR Cape in Chilmark - Pet Friendly

Chilmark, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(30)

$952.24

/ Nightly
Private vacation home

Classic Charming and Whimsical Martha’s Vineyard Home, with Private Beach

Aquinnah, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(30)

$1004.74

/ Nightly
Private vacation home

Walk to Beach Beautiful Ocean Views

Aquinnah, Massachusetts, United States

Bed 5

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(30)

$995.25

/ Nightly
Private vacation home

Spectacular Newly Renovated Home in Menemsha

Chilmark, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(30)

$781.90

/ Nightly
Private vacation home

Tucked Away on Tea Lane, Chilmark

Chilmark, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps

Most Popular Cities in Massachusetts