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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
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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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
Relaxing Windsor village apartment #2
1 bedroom, 1 bed, 1 bathroom
23–30 Nov
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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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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
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds, 1.5 bathrooms
16–21 Sept
4.89 out of 5 average rating, 93 reviews
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Guest favourite
Flat in Hartland
Sunny Studio Apartment in Hartland
1 bedroom, 1 bathroom
4–9 Nov
4.88 out of 5 average rating, 501 reviews
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Top guest favourite
Home in Cornish
Country Home next to Covered Bridge
3 bedrooms, 4 beds, 1.5 bathrooms
27 Oct – 1 Nov
4.96 out of 5 average rating, 166 reviews
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Guest favourite
Cabin in West Windsor
Scandinavian Style • Walls of Glass • Quiet Woods
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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Featured hotel
Hotel in Woodstock
Pet friendly queen
1 bedroom, 2 queen beds, 1 bathroom
21–26 Sept
New place to stay
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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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Guest favourite
Home in Hartland
19th Century Bohemian Barn House
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Oct
4.93 out of 5 average rating, 103 reviews
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Top guest favourite
Cabin in Weathersfield
Little Ascutney Post &Beam Chalet -Cozy near Okemo
2 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 41 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
Flat in Weathersfield
The Loft at Weathersfield
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 196 reviews
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Guest favourite
Home in West Windsor
Tranquility Farm 2
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Room in Weathersfield
The Oak Room - Ladoga
1 king bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 64 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