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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
13–18 Sept
5.0 out of 5 average rating, 28 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
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, 464 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
Room in Windsor
Fangs and Fuzz Room At All Hallows Inn B and B
1 king bed, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Room in Cornish
"Purple Room"—Fernald Hill Farm/Yatsevitch Forest
2 single beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 47 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
Guest favourite
Villa in Brownsville
2-Bedroom Villa w/ King, Queen & Private Balcony
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.79 out of 5 average rating, 78 reviews
Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed, 1.5 bathrooms
2–7 Sept
4.88 out of 5 average rating, 106 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
Top guest favourite
Tiny home in Hartland
Cabin on the Hill
1 bedroom, 2 beds, No bathroom
26–31 Oct
4.97 out of 5 average rating, 240 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, 97 reviews
Guest favourite
Room in Windsor
THE DOLL HOUSE - On a Lake/Trails
1 bed, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 13 reviews
Villa in Brownsville
Villa Near Biking and Hiking Trails
3 bedrooms, 4 beds, 3 bathrooms
26–31 Oct
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Guest suite in Brownsville/West Windsor
Cozy Guest Suite in VT Farmhouse
1 bedroom, 1 king bed, 1.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 214 reviews
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
Top guest favourite
Room in Cornish
Fitch Family Farm
1 queen bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 183 reviews