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Search results; Over 1,000 homes in Winchester

Superhost
Guest house in Winchester
The Higgle House: A Sweetwater Farm Stay
2 bedrooms, 2 beds, 1 private bathroom
28 Aug – 2 Sept
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4.87 out of 5 average rating, 91 reviews
Superhost
Flat in Winchester
The Beam House | Cozy Rustic Retreat in Winchester
1 bedroom, 2 beds, 1 bathroom
12–17 Aug
4.92 out of 5 average rating, 26 reviews
Guest favourite
Cabin in Winchester
Lakeside rustic seasonal cottage
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.83 out of 5 average rating, 30 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 8 reviews
Superhost
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.82 out of 5 average rating, 57 reviews
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Sept
4.86 out of 5 average rating, 163 reviews
Camper van/Motorhome in Chesterfield
Vintage Cruiser on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Tiny home in Chester
Tiny A-Frame Rest House in Woods near Mountains
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 134 reviews
Guest favourite
Cabin in Vernon
Haven: an off-grid cabin retreat
1 bedroom, 1 queen bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Yurt in Putney
Serene Yurt Near the Best of Southern Vermont
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Room in Greenfield
Eco-friendly room in quiet country home
1 queen bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 282 reviews
Guest favourite
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.94 out of 5 average rating, 1373 reviews
Top guest favourite
Bed and breakfast in Rindge
Rindge Glass Flower Rm1 PvtRoom, PvtBath, King Bed
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 182 reviews
Top guest favourite
Cabin in Warwick
Artsy Pine Cabin in the Woods
1 bedroom, 1 bed, 1 bathroom
13–18 Aug
4.97 out of 5 average rating, 236 reviews
Top guest favourite
Home in Dummerston
Barnside Cottage at Fruition Farm
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Newfane
Cozy Apartment
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 399 reviews
Top guest favourite
Room in Townshend
Rustic elegance at its best!
1 king bed, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 82 reviews
Guest favourite
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
4.9 out of 5 average rating, 142 reviews