Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
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 Windsor holiday rentals
Other great holiday rentals in Windsor
Guest favourite
Flat in Petersburg
4.85 out of 5 average rating, 151 reviewsThe Beer Diviner Brewery Apartment
Guest favourite
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Guest favourite
Flat in North Adams
4.91 out of 5 average rating, 114 reviewsCozy 1 bedroom 1/2 mile to MassMoca
Guest favourite
Flat in Shelburne Falls
4.96 out of 5 average rating, 294 reviewsAnnies’ Place by The Bridge of Flowers ~
Guest favourite
Flat in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Guest favourite
Farm stay in Pittsfield
4.99 out of 5 average rating, 107 reviewsPrivate 2nd-floor studio on a working produce farm
Guest favourite
Guest house in Northampton
5.0 out of 5 average rating, 277 reviewsMill River Cottage (pet friendly!)
Guest favourite
Cottage in Ashfield
4.97 out of 5 average rating, 302 reviewshope house
Destinations to explore
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