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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, Fall and Winter Days…
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, 470 reviews
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Top guest favourite
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
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Oct
5.0 out of 5 average rating, 41 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
19–24 Oct
4.89 out of 5 average rating, 93 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
Room 217 At All Hallows Inn B and B
1 bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 38 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, 243 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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Guest favourite
Room in Windsor
THE DOLL HOUSE - On a Lake/Trails
1 bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Cabin in West Windsor
Designer Cabin | Woodstock | Swimming Hole Nearby
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Cornish
Country Home next to Covered Bridge
3 bedrooms, 4 beds, 1.5 bathrooms
29 Oct – 3 Nov
4.96 out of 5 average rating, 166 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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Top guest favourite
Home in Reading
Hilltop Hideaway |Private, 3BR Home | 10 Acres
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 12 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, 218 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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Guest favourite
Dome in Reading
Super-private Geodesic Dome near Woodstock
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 18 reviews
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Home in West Windsor
Skyhawk Cabin - Refined Modern Getaway with Hot Tu
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.77 out of 5 average rating, 13 reviews