filters

Search results; Over 1,000 homes in Winchester

Photo 1 of 15
Superhost
Guest house in Winchester
The Higgle House: A Sweetwater Farm Stay
2 bedrooms, 2 beds, 1 private bathroom
1–6 Nov
,
4.86 out of 5 average rating, 92 reviews
Photo 1 of 13
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.84 out of 5 average rating, 61 reviews
Photo 1 of 29
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Nov
4.85 out of 5 average rating, 167 reviews
Photo 1 of 29
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
17–22 Oct
4.9 out of 5 average rating, 10 reviews
Photo 1 of 29
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 9 reviews
Photo 1 of 28
Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
1–6 Oct
New place to stay
Photo 1 of 13
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 196 reviews
Photo 1 of 29
Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms, 4 beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 14
Camper van/Motorhome in Chesterfield
Vintage Cruiser on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
Photo 1 of 29
Guest favourite
Home in Guilford
Vermont Mirror House
1 bedroom, 2 beds, 1 bathroom
13–18 Nov
4.95 out of 5 average rating, 161 reviews
Photo 1 of 29
Guest favourite
Treehouse in Stoddard
Handcrafted Treehouse · 2hr Boston · Fire + Stars
1 bedroom, 1 bathroom
12–17 Oct
4.92 out of 5 average rating, 133 reviews
Photo 1 of 28
Top guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 251 reviews
Photo 1 of 29
Guest favourite
Flat in Vernon
Deck, Mountain Views: Colorful Retreat in Vernon!
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.86 out of 5 average rating, 35 reviews
Photo 1 of 17
Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 54 reviews
Photo 1 of 29
Top guest favourite
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 202 reviews
Photo 1 of 6
Guest favourite
Room in Chesterfield
Waterfront Paradise - 1.3 mile to Brattleboro
2 beds, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 69 reviews
Photo 1 of 12
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 6 reviews
Photo 1 of 16
Top guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 67 reviews