Vacation rentals in Chester
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Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester
Guest favorite
Apartment in Leeds
4.99 out of 5 average rating, 114 reviewsPrivate Studio for a Sweet Getaway!
Sep 14 – 21
€ 151 per night
Guest favorite
Guest suite in Williamsburg
4.98 out of 5 average rating, 230 reviewsHappy Maples!
Jun 12 – 19
€ 138 per night
Guest favorite
Apartment in Shelburne Falls
4.98 out of 5 average rating, 487 reviewsIn town, newly renovated studio with private deck
Apr 10 – 17
€ 108 per night
Guest favorite
Guesthouse in Lenox
4.95 out of 5 average rating, 280 reviewsThe Granary at House on Golden Hill
Sep 3 – 10
€ 157 per night
Guest favorite
Guesthouse in Granby
4.99 out of 5 average rating, 706 reviewsWindy Top Cottage ~ A Romantic "European" Getaway
Mar 12 – 19
€ 182 per night
Guest favorite
Chalet in Otis
4.94 out of 5 average rating, 349 reviewsMid-Century Glass Octagon in the Berkshires
Apr 12 – 19
€ 393 per night
Guest favorite
Farm stay in Pittsfield
4.99 out of 5 average rating, 105 reviewsPrivate 2nd-floor studio on a working produce farm
Sep 19 – 26
€ 144 per night
Guest favorite
Cottage in Becket
4.95 out of 5 average rating, 126 reviewsCozy lakeside cottage
Sep 22 – 29
€ 354 per night
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