Holiday rentals in Berkshire County
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Top-rated holiday rentals in Berkshire County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Berkshire County holiday rentals
Other great holiday rentals in Berkshire County
Guest favourite
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
7–14 Mar
$157 SGD per night
Guest favourite
Flat in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
26 Dec – 2 Jan
$225 SGD per night
Guest favourite
Home in Great Barrington
4.96 out of 5 average rating, 212 reviewsJaw dropping mountain & lake views
22 Feb – 1 Mar
$975 SGD per night
Guest favourite
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
2–9 Oct
$170 SGD per night
Guest favourite
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
4–11 Jan
$228 SGD per night
Guest favourite
Home in Chester
4.96 out of 5 average rating, 310 reviewsRiverfront Getaway
28 Jul – 4 Aug
$249 SGD per night
Guest favourite
Guest suite in Hancock
4.83 out of 5 average rating, 154 reviewsCozy apartment near Jiminy Peak
5–12 Oct
$131 SGD per night
Guest favourite
Chalet in Otis
4.94 out of 5 average rating, 349 reviewsMid-Century Glass Octagon in the Berkshires
12–19 Apr
$511 SGD per night
Destinations to explore
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