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Search results; Over 1,000 homes in Windsor

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, 466 reviews
Top guest favourite
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, 29 reviews
Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
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
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, 93 reviews
Top guest favourite
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, 137 reviews
Guest favourite
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
6 bedrooms, 9 beds, 2.5 bathrooms
15–20 Oct
4.88 out of 5 average rating, 43 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
Top guest favourite
Home in Reading
Hilltop Hideaway |Private, 3BR Home | 10 Acres
3 bedrooms, 5 beds, 2 bathrooms
24–29 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Hartland
Sunny Studio Apartment in Hartland
1 bedroom, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 501 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
Home in West Windsor
Chuck's Place
3 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Room in Cornish
"Purple Room"—Fernald Hill Farm/Yatsevitch Forest
2 single beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
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, 49 reviews
Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed, 1.5 bathrooms
6–11 Sept
4.88 out of 5 average rating, 106 reviews
Guest favourite
Home in Hartland
19th Century Bohemian Barn House
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 103 reviews
Top guest favourite
Flat in Hartford
A Peaceful Brookside Vermont Retreat
2 bedrooms, 2 queen beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Plainfield
Historic Home on 17 acres of land. Go escape!
6 bedrooms, 7 beds, 5 bathrooms
8–13 Sept
4.9 out of 5 average rating, 157 reviews
Home in West Windsor
Skyhawk Cabin - Refined Modern Getaway with Hot Tu
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.77 out of 5 average rating, 13 reviews