Vacation rentals in Berkshire County
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Top-rated vacation rentals in Berkshire County
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 Berkshire County vacation rentals
Other great vacation rentals in Berkshire County
Guest favorite
Cabin in Cheshire
4.89 out of 5 average rating, 152 reviewsPrivate Paradise in the Berkshires
Nov 24 – Dec 1
R2,678 ZAR per night
Guest favorite
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
Mar 10 – 17
R2,169 ZAR per night
Guest favorite
Apartment in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
Dec 28 – Jan 4
R3,113 ZAR per night
Guest favorite
Home in Great Barrington
4.96 out of 5 average rating, 213 reviewsJaw dropping mountain & lake views
Jan 7 – 14
R13,468 ZAR per night
Guest favorite
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Feb 6 – 13
R3,152 ZAR per night
Guest favorite
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
Sep 13 – 20
R2,344 ZAR per night
Guest favorite
Guest suite in Austerlitz
4.86 out of 5 average rating, 137 reviewsRustic-Modern Studio - Near Hudson, Chatham, & GB
Feb 23 – Mar 2
R1,681 ZAR per night
Guest favorite
Apartment in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Jun 19 – 26
R1,378 ZAR per night
Destinations to explore
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