Chilmark Vacation Rentals - HolidayHomes base64Hash Chilmark Vacation Rentals - HolidayHomes

Chilmark Vacation Rentals

Browse 66 available vacation homes and compared across 4 trusted partners

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Top-Rated Vacation rentals in Chilmark

Book the highest-rated Chilmark vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Chilmark
Unwind in Guest House overlooking Menemsha Pond. Dogs ok Lv-2 EV charger.
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House Chilmark
Vacation home with barbeque, patio & garden | Nature view
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House Chilmark
Family-friendly vacation home with yard, terrace & barbecue | Nature view | Pets allowed
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House Chilmark
10 minutes walk to Lucy Vincent Beach
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House Chilmark
Vacation home with yard & barbeque
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House Chilmark
Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
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House Chilmark
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
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House Chilmark
Vacation home with terrace, grill & garden | Nature view
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House Chilmark
Child-friendly beautiful house with yard, jacuzzi & patio | Nature view
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House Chilmark
Children-friendly nice vacation home with garden, patio & barbecue | Next to the beach | Pets are welcome
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House Chilmark
House with patio, barbeque & yard | Nature view
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House Chilmark
Spacious house | Good for workation
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House Chilmark
Classic Modern House on its Own Point of Land with Astounding Views
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House Chilmark
3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
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House Chilmark
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
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Top 15 most Recommended Vacation Rentals in Chilmark

Discover your ideal Chilmark vacation rental with real-time comparisons of 66 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Chilmark
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming vacation home with patio, barbecue & yard | Pets are welcome

Chilmark, Dukes County, Massachusetts, United States
This house rental in Menemsha accommodates 8 guests and features a spacious yard for outdoor activities.
from $475
per night
(4)
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House Chilmark
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly house with yard, BBQ & jacuzzi | Nature view | Perfect for remote work

Chilmark, Dukes County, Massachusetts, United States
This house rental in Menemsha accommodates 8 guests and features a cozy fireplace for a comfortable stay.
from $1,022
per night
(14)
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House Chilmark
House ∙ 9 guests ∙ 4 bedrooms

House with garden, patio & BBQ

Chilmark, Dukes County, Massachusetts, United States
Spacious house rental in Menemsha accommodates 9 guests and features a family-friendly yard for outdoor enjoyment.
from $557
per night
(10)
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House Chilmark
House ∙ 13 guests ∙ 6 bedrooms

House with BBQ, terrace & yard | Nature view

Chilmark, Dukes County, Massachusetts, United States
This house rental in Menemsha accommodates 13 guests and features a family-friendly kitchen for enjoyable gatherings.
from $809
per night
(46)
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House Chilmark
House ∙ 8 guests ∙ 5 bedrooms

Family-friendly beautiful vacation home with yard, terrace & grill

Chilmark, Dukes County, Massachusetts, United States
This house rental in Menemsha accommodates 8 guests and features beach access for a delightful seaside experience.
from $1,115
per night
(8)
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House Chilmark
House ∙ 8 guests ∙ 4 bedrooms

Nice house with pool & terrace

Chilmark, Dukes County, Massachusetts, United States
This house rental in Menemsha accommodates 8 guests and features a fully equipped kitchen for your convenience.
from $801
per night
(16)
View deal
House Chilmark
House ∙ 10 guests ∙ 3 bedrooms

Fully equipped vacation home with grill, patio & garden | Perfect for remote work

Chilmark, Dukes County, Massachusetts, United States
This house rental in Menemsha accommodates 10 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $832
per night
(42)
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Cabin Chilmark
Cabin ∙ 5 guests ∙ 2 bedrooms

Fully equipped cottage with barbecue & patio | Beach nearby | Pets are welcome

Chilmark, Dukes County, Massachusetts, United States
This cozy cabin in Chilmark accommodates 5 guests and features a fully equipped kitchen for a comfortable stay.
from $517
per night
(10)
View deal
Cabin Chilmark
Cabin ∙ 10 guests ∙ 4 bedrooms

Fully equipped cottage with yard, barbecue & patio | Nature view | Pet-friendly

Chilmark, Dukes County, Massachusetts, United States
This spacious cabin in Menemsha accommodates 10 guests and features a cozy fireplace for warm gatherings.
from $676
per night
(10)
View deal

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