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Search results; Over 1,000 homes in Windsor

Top guest favourite
Home in Windsor
Custom cabin on Mt Ascutney, sweeping Hill Views
2 bedrooms, 5 beds, 2 private bathrooms
8–13 Aug
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4.98 out of 5 average rating, 132 reviews
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
4.97 out of 5 average rating, 458 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Nov
Top guest favourite
Flat in Windsor
Charming apartment on the Windsor Green
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Aug
Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
5.0 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
4.89 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
4.87 out of 5 average rating, 38 reviews, 6 bedrooms, 9 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Room in Cornish
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
4.97 out of 5 average rating, 79 reviews, 1 bed, 1 bathroom
7–12 Aug
Top guest favourite
Cabin in West Windsor
Stylish Loft Adventure Hub Near Woodstock & GMHA
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Room in Windsor
Room 217 At All Hallows Inn B and B
5.0 out of 5 average rating, 35 reviews, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Cabin in West Windsor
Peaceful Vermont Cottage w/ Outdoor Sauna!
4.83 out of 5 average rating, 78 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in West Windsor
Meadow View. 35 acres outside your door!
4.98 out of 5 average rating, 234 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Villa in Brownsville
Villa Near Biking and Hiking Trails
4.82 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Cabin in West Windsor
Cabin on the Hill, Vermont
4.92 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in West Windsor
Birdie's Nest Guesthouse
4.98 out of 5 average rating, 183 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in West Windsor
Chuck's Place
4.96 out of 5 average rating, 90 reviews, 3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Villa in Brownsville
2-Bedroom Villa w/ King, Queen & Private Balcony
4.79 out of 5 average rating, 77 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Cabin in Weathersfield
Cozy a-frame: New kitchen, mins to hiking + skiing
5.0 out of 5 average rating, 44 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Home in Plymouth
Charming pet-friendly retreat in the Vermont woods
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Home in Hartland
19th Century Bohemian Barn House
4.93 out of 5 average rating, 100 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug