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Search results; Over 1,000 homes in Winchester

Superhost
Flat in Winchester
The Beam House | Cozy Rustic Retreat in Winchester
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
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4.89 out of 5 average rating, 27 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.89 out of 5 average rating, 9 reviews
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.83 out of 5 average rating, 59 reviews
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Sept
4.85 out of 5 average rating, 165 reviews
Top guest favourite
Room in Chesterfield
Peaceful Poet’s Farm
1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 192 reviews
Camper van/Motorhome in Chesterfield
Vintage Cruiser on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Room in Brattleboro
Maple St. Guest Rm Q Bed & Shared Bath
1 queen bed, 1 bathroom
17–22 Sept
4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Room in Greenfield
Eco-friendly room in quiet country home
1 queen bed, 1 bathroom
10–15 Sept
4.95 out of 5 average rating, 283 reviews
Top guest favourite
Bed and breakfast in Rindge
Rindge Glass Flower Rm1 PvtRoom, PvtBath, King Bed
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
4.99 out of 5 average rating, 183 reviews
Top guest favourite
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 193 reviews
Top guest favourite
Room in Townshend
Rustic elegance at its best!
1 king bed, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cabin in Warwick
Artsy Pine Cabin in the Woods
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 236 reviews
Top guest favourite
Tiny home in Putney
Honeycrisp Cottage - A Tiny Timber Frame
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.94 out of 5 average rating, 820 reviews
Top guest favourite
Guest house in Hancock
Historic Coopers' Barn | Waterfront Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 76 reviews