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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
13–18 Sept
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4.83 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds
8–13 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds
7–12 Sept
4.83 out of 5 average rating, 60 reviews
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds
7–12 Sept
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds
14–19 Sept
4.93 out of 5 average rating, 88 reviews
Top guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 249 reviews
Superhost
Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Keene
The Murdock Suite @ The Large House
2 bedrooms, 2 beds
7–12 Sept
4.95 out of 5 average rating, 80 reviews
Guest favourite
Home in Jaffrey
John's Mountain Hideaway
3 bedrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Spofford
A-Frame Cottage @ Spofford Lake with Dock Slip
3 bedrooms, 4 beds
9–14 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Colrain
Secluded Farmhouse Retreat - stunning views
4 bedrooms, 6 beds
14–19 Sept
4.94 out of 5 average rating, 198 reviews
Guest favourite
Cabin in Brattleboro
Log Cabin on Maple Sugar Farm
4 bedrooms, 5 beds
23–28 Sept
4.91 out of 5 average rating, 32 reviews
Home in Athol
The Rafors Lake House
4 bedrooms, 7 queen beds
13–18 Sept
New place to stay
Guest favourite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - entire home
3 bedrooms, 5 beds
8–13 Sept
5.0 out of 5 average rating, 36 reviews
Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 76 reviews
Top guest favourite
Home in Sunderland
Farmhouse on working dairy farm
4 bedrooms, 6 beds
20–25 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Chesterfield
Charming Country Home
2 bedrooms, 3 beds
3–8 Oct
4.98 out of 5 average rating, 315 reviews