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
Get the amount of space that is right for you
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor
Guest favourite
Flat in Stamford
4.86 out of 5 average rating, 274 reviewsGetaway Near Mass MoCA, Great Hiking, Scenic Views
4–11 Feb
£114 per night
Guest favourite
Flat in Greenfield
4.96 out of 5 average rating, 267 reviewsMohawk Trail View/ private apt. no cleaning Fee
24–31 Jul
£96 per night
Guest favourite
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
28 Nov – 5 Dec
£126 per night
Guest favourite
Flat in North Adams
4.91 out of 5 average rating, 109 reviewsCozy 1 bedroom 1/2 mile to MassMoca
29 Sept – 6 Oct
£91 per night
Guest favourite
Guest house in Lenox
4.95 out of 5 average rating, 276 reviewsThe Granary at House on Golden Hill
5–12 Sept
£135 per night
Guest favourite
Flat in Adams
4.88 out of 5 average rating, 57 reviewsMountain Living, 1-bedroom unit, outdoor hot-tub
5–12 Sept
£97 per night
Guest favourite
Flat in Pittsfield
4.92 out of 5 average rating, 25 reviewsComfortable Pittsfield Loft
7–14 Nov
£74 per night
Guest favourite
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
30 Nov – 7 Dec
£117 per night
Destinations to explore
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