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 favourite
Apartment in Stamford
4.86 out of 5 average rating, 274 reviewsGetaway Near Mass MoCA, Great Hiking, Scenic Views
Feb. 4 – 11
$193 CAD per night
Guest favourite
Apartment in Greenfield
4.96 out of 5 average rating, 268 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul. 24 – 31
$161 CAD per night
Guest favourite
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
Nov. 28 – Dec. 5
$212 CAD per night
Guest favourite
Apartment in North Adams
4.91 out of 5 average rating, 109 reviewsCozy 1 bedroom 1/2 mile to MassMoca
Sep. 29 – Oct. 6
$153 CAD per night
Guest favourite
Guesthouse in Lenox
4.95 out of 5 average rating, 276 reviewsThe Granary at House on Golden Hill
Sep. 5 – 12
$229 CAD per night
Guest favourite
Apartment in Adams
4.88 out of 5 average rating, 57 reviewsMountain Living, 1-bedroom unit, outdoor hot-tub
Sep. 5 – 12
$164 CAD per night
Guest favourite
Apartment in Pittsfield
4.92 out of 5 average rating, 25 reviewsComfortable Pittsfield Loft
Nov. 7 – 14
$125 CAD per night
Guest favourite
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Nov. 30 – Dec. 7
$197 CAD per night
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