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Search results; Over 1,000 homes in Winchester

Superhost
Cabin in Winchester
Lakeside rustic seasonal cottage
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.83 out of 5 average rating, 36 reviews
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
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.83 out of 5 average rating, 60 reviews
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Swanzey
Swanzey Retreat-serene yet close to Keene
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.88 out of 5 average rating, 17 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, 14 reviews
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, 249 reviews
Top guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
3 bedrooms, 7 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 33 reviews
Superhost
Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 46 reviews
Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 77 reviews
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
Top guest favourite
Home in Sunderland
Farmhouse on working dairy farm
4 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 64 reviews
Guest favourite
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
15–22 Sept
4.88 out of 5 average rating, 32 reviews
Top 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
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
Superhost
Cottage in Harrisville
The Monadnock Manse
8 bedrooms, 15 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews