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Search results; Over 1,000 homes in Windsor

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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, 464 reviews
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Flat in Windsor
Charming apartment on the Windsor Green
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 27 reviews
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Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 3 reviews
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Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 41 reviews
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Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds, 1.5 bathrooms
7–12 Sept
4.89 out of 5 average rating, 93 reviews
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Home in Windsor
Custom cabin on Mt Ascutney, with faraway views
2 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.97 out of 5 average rating, 136 reviews
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Home in Cornish
Country Home next to Covered Bridge
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Oct
4.96 out of 5 average rating, 166 reviews
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Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed, 1.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 106 reviews
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Dome in Reading
Super-private Geodesic Dome near Woodstock
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 18 reviews
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Home in Cavendish
Midcentury Hillside Retreat - Summer Paradise
3 bedrooms, 6 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 134 reviews
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Home in West Windsor
Gorgeous and Secluded Log Home near Woodstock, Vt
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.97 out of 5 average rating, 76 reviews
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Cabin in Weathersfield
A-Frame | Ski/Hike | Dog-Friendly | New Back Deck
2 bedrooms, 3 beds, 1.5 bathrooms
7–13 Sept
5.0 out of 5 average rating, 48 reviews
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Room in Cornish
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
1 single bed, 1 bathroom
9–14 Sept
4.98 out of 5 average rating, 86 reviews
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Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
6 bedrooms, 9 beds, 2.5 bathrooms
8–13 Sept
4.88 out of 5 average rating, 42 reviews
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Room in Weathersfield
The Oak Room - Ladoga
1 king bed, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 63 reviews
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Townhouse in West Windsor
Mountain Edge Living
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Oct
4.96 out of 5 average rating, 57 reviews
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Room in Windsor
Fangs and Fuzz Room At All Hallows Inn B and B
1 king bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 59 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
8–13 Sept
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in West Windsor
Tranquility Farm 2
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 16 reviews