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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, 467 reviews
Top guest favourite
Flat in Windsor
Charming apartment on the Windsor Green
1 bedroom, 2 beds
12–17 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 41 reviews
Flat in Windsor
The Hideout
2 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds
8–13 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
17–22 Oct
4.97 out of 5 average rating, 137 reviews
Top guest favourite
Home in Reading
Hilltop Hideaway |Private, 3BR Home | 10 Acres
3 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Villa in Brownsville
2-Bedroom Villa w/ King, Queen & Private Balcony
2 bedrooms, 3 beds
23–28 Oct
4.8 out of 5 average rating, 79 reviews
Top guest favourite
Home in West Windsor
Chuck's Place
3 bedrooms, 6 beds
19–24 Sept
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Room in Windsor
Fangs and Fuzz Room At All Hallows Inn B and B
1 king bed
20–25 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
6 bedrooms, 9 beds
15–20 Oct
4.88 out of 5 average rating, 43 reviews
Top guest favourite
Tiny home in Hartland
Cabin on the Hill
1 bedroom, 2 beds
26–31 Oct
4.97 out of 5 average rating, 241 reviews
Villa in Brownsville
Villa Near Biking and Hiking Trails
3 bedrooms, 4 beds
27 Oct – 1 Nov
4.82 out of 5 average rating, 11 reviews
Guest favourite
Room in Windsor
THE DOLL HOUSE - On a Lake/Trails
1 bed
9–14 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Room in Cornish
"Purple Room"—Fernald Hill Farm/Yatsevitch Forest
2 single beds
4–9 Oct
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Home in Cavendish
Midcentury Hillside Retreat - Summer Paradise
3 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 135 reviews
Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed
8–13 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
26–31 Oct
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
29 Oct – 3 Nov
5.0 out of 5 average rating, 49 reviews