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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
13–18 Sept
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4.89 out of 5 average rating, 27 reviews
Superhost
Cabin in Winchester
Lakeside rustic seasonal cottage
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
7–12 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
7–12 Sept
4.83 out of 5 average rating, 60 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
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
6–11 Sept
4.98 out of 5 average rating, 46 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, 13 reviews
Top guest favourite
Flat in Keene
The Murdock Suite @ The Large House
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 249 reviews
Top guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.93 out of 5 average rating, 88 reviews
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, 24 reviews
Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 76 reviews
Guest favourite
Home in Jaffrey
John's Mountain Hideaway
3 bedrooms, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Sunderland
Farmhouse on working dairy farm
4 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Guest favourite
Cabin in Brattleboro
Log Cabin on Maple Sugar Farm
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Sept
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Home in Colrain
Secluded Farmhouse Retreat - stunning views
4 bedrooms, 6 beds, 3.5 bathrooms
14–19 Sept
4.94 out of 5 average rating, 198 reviews
Top guest favourite
Home in Rindge
The Shoreline
5 bedrooms, 13 beds, 2.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 51 reviews