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Long-Term Vacation Rentals in Chilmark

Rental homes are available for an extended stay of a month or more at a time. While some rentals by owner will be available for long-term stays during the summer or year-round, majority are available during the off-season (fall, winter and spring). Monthly prices may vary depending on the number in your party and length of stay.

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 5


Very Charming, Roomy Three Bedroom Home
2 baths
Sleeps 8

All in the town of Chilmark.

Contact: John and Caroline Moore., Property ID: 15956

Chilmark Casita - New Listing! Newly Renovated w/Central AC!
2 baths
Sleeps 5

February, March, and April are available for $1,500-$2,500 a week.

Contact: Jo, Property ID: 34169

On Upper Chilmark Pond overlooking Lucy Vincent Beach
1 bath
Sleeps 4

Available in Town of Chilmark.

Contact: John and Caroline Moore., Property ID: 13169

Quiet, Secluded Chilmark Cottage
1 bath
Sleeps 4


Contact: Brian & Caroline Giles, Property ID: 22294

Storybook Cottage in Chilmark
1 bath
Sleeps 2

Long and short term winter rental available.

Contact: Alyson at Karen M. Overtoom Real Estate, Property ID: 31847