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Search results; Over 1,000 homes in Windsor

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Top guest favourite
Home in Windsor
Custom cabin on Mt Ascutney, with faraway views
2 bedrooms, 5 beds, 2 private bathrooms
17–22 Oct
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4.97 out of 5 average rating, 138 reviews
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Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 469 reviews
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Flat in Windsor
Charming apartment on the Windsor Green
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 30 reviews
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Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds, 1.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 93 reviews
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Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed, 1.5 bathrooms
20–25 Sept
4.88 out of 5 average rating, 106 reviews
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Top guest favourite
Room in Windsor
Fangs and Fuzz Room At All Hallows Inn B and B
1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Tiny home in Hartland
Cabin on the Hill
1 bedroom, 2 beds, No bathroom
1–6 Nov
4.97 out of 5 average rating, 241 reviews
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Guest favourite
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
6 bedrooms, 9 beds, 2.5 bathrooms
21–26 Sept
4.88 out of 5 average rating, 43 reviews
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Top guest favourite
Guest suite in Plainfield
Renovated 1817 Hobby Farm Close to Dartmouth
1 bedroom, 3 beds, 1 bathroom
22–27 Oct
4.97 out of 5 average rating, 275 reviews
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Top guest favourite
Room in Cornish
Fitch Family Farm
1 queen bed, 1 bathroom
3–8 Dec
4.91 out of 5 average rating, 184 reviews
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Top guest favourite
Guest suite in Windsor
Charming Brick Cape near Windsor Grasslands area.
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 114 reviews
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Flat in Windsor
Relaxing Windsor village apartment #2
1 bedroom, 1 bed, 1 bathroom
23–30 Nov
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Guest favourite
Room in Windsor
THE DOLL HOUSE - On a Lake/Trails
1 bed, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Guest house in Hartland
Cozy Cottage close to central VT&NH Grand Piano!
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 217 reviews
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Top guest favourite
Cabin in Weathersfield
Dog-Friendly | Fenced Yard | Fall Hikes & Foliage
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 50 reviews
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Guest favourite
Dome in Reading
Super-private Geodesic Dome near Woodstock
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 18 reviews
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Room in Cornish
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
1 single bed, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 89 reviews