Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor
Guest favorite
Home in Dalton
4.99 out of 5 average rating, 120 reviewsCleveland House - renovated Berkshires' gem.
Jan 7 – 14
G$96,948 GYD per night
Guest favorite
Apartment in Greenfield
4.96 out of 5 average rating, 268 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul 3 – 10
G$22,194 GYD per night
Guest favorite
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
Jan 1 – 8
G$30,034 GYD per night
Guest favorite
Guesthouse in Northampton
5.0 out of 5 average rating, 272 reviewsMill River Cottage (pet friendly!)
Sep 8 – 15
G$25,192 GYD per night
Guest favorite
Apartment in Petersburg
4.85 out of 5 average rating, 147 reviewsThe Beer Diviner Brewery Apartment
Jan 10 – 17
G$14,223 GYD per night
Guest favorite
Cottage in Petersham
4.99 out of 5 average rating, 149 reviewsCider House Cottage
Dec 20 – 27
G$29,419 GYD per night
Superhost
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jun 19 – 26
G$22,296 GYD per night
Guest favorite
Barn in Marlboro
4.95 out of 5 average rating, 263 reviewsThe Studio With a View. Bring your dog, too!
Jan 7 – 14
G$29,244 GYD per night
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