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 29
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 10 reviews
Photo 1 of 13
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.83 out of 5 average rating, 60 reviews
Photo 1 of 29
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 9 reviews
Photo 1 of 6
Top guest favourite
Rooms in Hinsdale
Country Retreat
2 bedrooms, 3 queen beds, 1 bathroom
4–9 Jun
4.95 out of 5 average rating, 57 reviews
Photo 1 of 27
Top guest favourite
Home in Putney
Charming Putney Village Home!
4 bedrooms, 7 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 21 reviews
Photo 1 of 26
Top guest favourite
Flat in Keene
The Murdock Suite @ The Large House
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 80 reviews
Photo 1 of 29
Guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.93 out of 5 average rating, 88 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
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 146 reviews
Photo 1 of 29
Guest favourite
Home in Marlborough
4 BR Monadnock View Luxury Chalet
4 bedrooms, 5 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 25 reviews
Photo 1 of 18
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, 17 reviews
Photo 1 of 16
Top guest favourite
Home in Shutesbury
Cute A-frame near Lake Wyola!
2 bedrooms, 4 beds, 1 bathroom
16–21 Nov
5.0 out of 5 average rating, 12 reviews
Photo 1 of 29
Top guest favourite
Yurt in Dover
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
3 bedrooms, 4 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.93 out of 5 average rating, 137 reviews
Photo 1 of 29
Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 46 reviews
Photo 1 of 18
Flat in Marlborough
Historical home with garden, apples and sunporch!
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
New place to stay
Photo 1 of 29
Guest favourite
Flat in Dummerston
1850’s Barn Retreat
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 514 reviews
Photo 1 of 29
Guest favourite
Home in Gardner
Lodge at Kendall Pond · Hot Tub & Private Dock
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.88 out of 5 average rating, 24 reviews
Photo 1 of 29
Guest favourite
Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.91 out of 5 average rating, 67 reviews