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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, 25 reviews
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Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 3 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
7–12 Sept
4.89 out of 5 average rating, 92 reviews
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Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 41 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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Top guest favourite
Cabin in Weathersfield
A-Frame | Ski/Hike | Dog-Friendly | New Back Deck
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 48 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
1–6 Sept
4.88 out of 5 average rating, 106 reviews
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Home in Cavendish
Midcentury Hillside Retreat - Summer Paradise
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 134 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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Superhost
Guest suite in Brownsville/West Windsor
Cozy Guest Suite in VT Farmhouse
1 bedroom, 1 king bed, 1.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 213 reviews
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Guest favourite
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 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 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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Top guest favourite
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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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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Guest house in Hartland
Cozy - Killington 40 min. Woodstock-Hanover-Piano!
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.97 out of 5 average rating, 213 reviews
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Superhost
Room in Cornish
Fitch Family Farm
1 queen bed, 1 bathroom
10–15 Sept
4.91 out of 5 average rating, 183 reviews
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Guest favourite
Home in Hartland
19th Century Bohemian Barn House
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Sept
4.93 out of 5 average rating, 103 reviews