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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
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
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
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
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.95 out of 5 average rating, 192 reviews
Guest favourite
Yurt in Dover
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.92 out of 5 average rating, 126 reviews
Top guest favourite
Guest house in Chesterfield
House on a hill
1 bedroom, 1 bed, 1 bathroom
8–13 Sept
4.98 out of 5 average rating, 112 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
Campsite in Winchester
Escape to our serene RV pad in Winchester, NH
1 bedroom, 1 bed, 1 bathroom
12–17 Aug
Home in Shutesbury
Cute A-frame near Lake Wyola!
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Brattleboro
Guest House @ 120
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 112 reviews
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Chesterfield
Peaceful Poet’s Farm
1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Treehouse in Jamaica
The Treehouse at Frog Pond Farm
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Cabin in New Salem
Rustic cabin with A/C at historic orchard & cidery
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Brattleboro
River View apartment
1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Cabin in Dummerston
Cozy Riverfront Cabin-Ski, Swim, Fish, Float, Hike
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
4.97 out of 5 average rating, 68 reviews