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
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Apr 19 – 26
ﺩ.ﺇ402 per night
Guest favorite
Apartment in Greenfield
4.96 out of 5 average rating, 269 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul 3 – 10
ﺩ.ﺇ399 per night
Superhost
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jun 20 – 27
ﺩ.ﺇ400 per night
Guest favorite
Guesthouse in Northampton
5.0 out of 5 average rating, 273 reviewsMill River Cottage (pet friendly!)
Jan 7 – 14
ﺩ.ﺇ453 per night
Guest favorite
Guesthouse in Lenox
4.95 out of 5 average rating, 280 reviewsThe Granary at House on Golden Hill
Sep 4 – 11
ﺩ.ﺇ547 per night
Guest favorite
Apartment in Petersburg
4.85 out of 5 average rating, 148 reviewsThe Beer Diviner Brewery Apartment
Jan 30 – Feb 6
ﺩ.ﺇ256 per night
Guest favorite
Apartment in North Adams
4.95 out of 5 average rating, 713 reviewsGuest Apt. Near MCLA & MASS MoCA
Aug 21 – 28
ﺩ.ﺇ403 per night
Guest favorite
Cottage in Petersham
4.99 out of 5 average rating, 150 reviewsCider House Cottage
Oct 27 – Nov 3
ﺩ.ﺇ522 per night
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