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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
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
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
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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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
19–24 Sept
New place to stay
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Guest favourite
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
18–25 Sept
4.88 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds, 1 bathroom
9–14 Oct
5.0 out of 5 average rating, 6 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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Camper van/Motorhome in Chesterfield
Vintage Cruiser on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
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Top guest favourite
Guest suite in Brattleboro
Charming studio in renovated 19th century church.
2 beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 644 reviews
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Top guest favourite
Guest house in Chesterfield
House on a hill
1 bedroom, 1 bed, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 115 reviews
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Guest favourite
Home in Chesterfield
Lakehouse Getaway
2 bedrooms, 6 beds, 1.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 50 reviews
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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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Top guest favourite
Yurt in Wendell
Cozy yurt in the woods.
1 bedroom, 1 bed, WC
19–24 Sept
5.0 out of 5 average rating, 36 reviews
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Top guest favourite
Campsite in Townshend
Camp on our farm (and gaze at the stars)
WC
20–25 Sept
5.0 out of 5 average rating, 113 reviews
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Guest favourite
Room in Chesterfield
Waterfront Paradise - 1.3 mile to Brattleboro
2 beds, 1 bathroom
29 Sept – 4 Oct
4.93 out of 5 average rating, 68 reviews
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Guest favourite
Home in Dummerston
Woodsy Retreat Near Skiing, Private Pool in Summer
2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Oct
4.9 out of 5 average rating, 48 reviews
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Top guest favourite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 77 reviews