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Search results; Over 1,000 homes in Windsor

Top guest favourite
Home in Windsor
Stylish Vermont Cabin | Views · Trails · Luxe
2 bedrooms, 5 beds, 2 private bathrooms
8–13 Aug
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4.98 out of 5 average rating, 131 reviews
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds
16–21 Nov
4.97 out of 5 average rating, 455 reviews
Top guest favourite
Flat in Windsor
Charming apartment on the Windsor Green
1 bedroom, 2 beds
9–14 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in West Windsor
Chuck's Place
3 bedrooms, 6 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 90 reviews
Top guest favourite
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
6 bedrooms, 9 beds
15–20 Aug
4.95 out of 5 average rating, 37 reviews
Guest favourite
Cabin in West Windsor
Peaceful Vermont Cottage w/ Outdoor Sauna!
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.83 out of 5 average rating, 78 reviews
Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds
21–26 Jul
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in West Windsor
Meadow View. 35 acres outside your door!
1 bedroom, 1 king bed
2–7 Aug
4.98 out of 5 average rating, 233 reviews
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds
24–29 Jul
4.89 out of 5 average rating, 91 reviews
Top guest favourite
Room in Windsor
Room 217 At All Hallows Inn B and B
1 bed
25–30 Jul
5.0 out of 5 average rating, 35 reviews
Guest favourite
Cabin in Weathersfield
Cozy a-frame w loft, new kitchen + mins to hiking
2 bedrooms, 3 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in West Windsor
Birdie's Nest Guesthouse
1 bedroom, 1 bed
26–31 Jul
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Tiny home in Hartland
Cabin on the Hill
1 bedroom, 2 beds
23–28 Aug
4.97 out of 5 average rating, 234 reviews
Top guest favourite
Flat in Weathersfield
Cute VT Bungalow With 180 Degree View of NH
1 bedroom, 1 queen bed
26–31 Jul
4.97 out of 5 average rating, 154 reviews
Guest favourite
Home in Reading
Hilltop Hideaway |Private, 3BR Home | 10 Acres
3 bedrooms, 4 beds
26–31 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Villa in Brownsville
2-Bedroom Villa w/ King, Queen & Private Balcony
2 bedrooms, 3 beds
17–22 Aug
4.79 out of 5 average rating, 77 reviews
Guest favourite
Shipping container in Ludlow
Luxury Container Home with Sauna & Heated Pool
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Barn in Woodstock
THE LOFT, stunning views from a timber framed barn
2 bedrooms, 2 beds
31 Aug – 5 Sept
4.99 out of 5 average rating, 311 reviews
Top guest favourite
Yurt in Newport
Bartlett's Blueberry Farm Yurt
1 bedroom, 2 beds
22–27 Aug
5.0 out of 5 average rating, 83 reviews