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Search results; Over 1,000 homes in Winchester

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Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 shared bathrooms
3–8 Nov
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4.85 out of 5 average rating, 167 reviews
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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
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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
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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
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Rooms in Northfield
Deerfield King Suite at Centennial House B&B
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
New place to stay
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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
27 Sept – 2 Oct
New place to stay
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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
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Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 77 reviews
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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
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Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
3 bedrooms, 7 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Cottage in Chesterfield
Modern Luxury on the Lake
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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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, 65 reviews
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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
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Guest favourite
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
20–27 Sept
4.88 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Keene
Family-Friendly 3BR Historic Home – Walk to Keene
3 bedrooms, 3 queen beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Colrain
Secluded Farmhouse Retreat - stunning views
4 bedrooms, 6 beds, 3.5 bathrooms
26–31 Oct
4.94 out of 5 average rating, 199 reviews
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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
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Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 105 reviews
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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