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Search results; Over 1,000 homes in Windsor

Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds, 1 private bathroom
16–21 Nov
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4.97 out of 5 average rating, 469 reviews
Top guest favourite
Flat in Windsor
Charming apartment on the Windsor Green
1 bedroom, 2 beds
25–30 Oct
5.0 out of 5 average rating, 30 reviews
Flat in Windsor
The Hideout
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Hotel in Woodstock
Standard two queen
1 bedroom, 2 queen beds
30 Apr – 5 May
New place to stay
Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds
15–20 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds
14–19 Sept
4.89 out of 5 average rating, 93 reviews
Top guest favourite
Home in Cornish
Country Home next to Covered Bridge
3 bedrooms, 4 beds
23–28 Oct
4.96 out of 5 average rating, 166 reviews
Top guest favourite
Room in Windsor
Fangs and Fuzz Room At All Hallows Inn B and B
1 king bed
20–25 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed
14–19 Sept
4.88 out of 5 average rating, 106 reviews
Top guest favourite
Home in Windsor
Custom cabin on Mt Ascutney, with faraway views
2 bedrooms, 5 beds
17–22 Oct
4.97 out of 5 average rating, 137 reviews
Guest favourite
Home in West Windsor
Tranquility Farm 2
3 bedrooms, 3 beds
14–19 Sept
5.0 out of 5 average rating, 17 reviews
Home in Claremont
Located in quiet neighborhood of Claremont
3 bedrooms, 3 beds
14–19 Sept
New place to stay
Guest favourite
Cabin in West Windsor
Scandinavian Style • Walls of Glass • Quiet Woods
2 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Villa in Brownsville
2-Bedroom Villa w/ King, Queen & Private Balcony
2 bedrooms, 3 beds
27 Oct – 1 Nov
4.8 out of 5 average rating, 79 reviews
Top guest favourite
Cabin in Weathersfield
Little Ascutney Post &Beam Chalet -Cozy near Okemo
2 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Reading
Hilltop Hideaway |Private, 3BR Home | 10 Acres
3 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Hartland
19th Century Bohemian Barn House
2 bedrooms, 2 queen beds
26–31 Oct
4.93 out of 5 average rating, 103 reviews
Top guest favourite
Cabin in Weathersfield
Dog-Friendly | Fenced Yard | Fall Hikes & Foliage
2 bedrooms, 3 beds
16–21 Oct
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Cavendish
Midcentury Hillside Retreat - Summer Paradise
3 bedrooms, 6 beds
10–15 Nov
5.0 out of 5 average rating, 135 reviews