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Search results; Over 1,000 homes in Windsor

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, 137 reviews
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
Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 41 reviews
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
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds, 1.5 bathrooms
14–19 Sept
4.89 out of 5 average rating, 93 reviews
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
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
Top guest favourite
Room in Cornish
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
1 single bed, 1 bathroom
17–22 Oct
4.98 out of 5 average rating, 89 reviews
Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed, 1.5 bathrooms
14–19 Sept
4.88 out of 5 average rating, 106 reviews
Top guest favourite
Home in West Windsor
Chuck's Place
3 bedrooms, 6 beds, 2 bathrooms
19–24 Sept
4.96 out of 5 average rating, 99 reviews
Guest favourite
Villa in Brownsville
2-Bedroom Villa w/ King, Queen & Private Balcony
2 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.8 out of 5 average rating, 79 reviews
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
Top guest favourite
Cabin in Weathersfield
Dog-Friendly | Fenced Yard | Fall Hikes & Foliage
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Oct
5.0 out of 5 average rating, 50 reviews
Home in West Windsor
Skyhawk Cabin - Refined Modern Getaway with Hot Tu
4 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.77 out of 5 average rating, 13 reviews
Top guest favourite
Room in Cornish
Fitch Family Farm
1 queen bed, 1 bathroom
11–16 Oct
4.91 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Hartford
A Peaceful Brookside Vermont Retreat
2 bedrooms, 2 queen beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 54 reviews
Villa in Brownsville
Villa Near Biking and Hiking Trails
3 bedrooms, 4 beds, 3 bathrooms
27 Oct – 1 Nov
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Plainfield
Historic Home on 17 acres of land. Go escape!
6 bedrooms, 7 beds, 5 bathrooms
16–21 Sept
4.9 out of 5 average rating, 157 reviews