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Search results; Over 1,000 places in Winchester

Guest favourite
Flat in Winchester
Downtown Loft above Winery and Distillery
1 double bed
7–12 Apr
4.93 out of 5 average rating, 159 reviews
Guest favourite
Townhouse in Winchester
Timber Frame Loft
1 queen bed
15–20 Apr
4.88 out of 5 average rating, 66 reviews
Superhost
Home in Winchester
Dragonfly Cottages: A Sweetwater Stay
4 beds
5–10 Apr
New place to stay
Guest favourite
Guest house in Winchester
The Higgle House: A Sweetwater Farm Stay
2 queen beds
1–6 Apr
4.89 out of 5 average rating, 57 reviews
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
3 beds
11–16 May
4.86 out of 5 average rating, 56 reviews
Guest favourite
Holiday home in Winchester
Lakefront Elegance with your own private beach
2 beds
1–6 May
5.0 out of 5 average rating, 9 reviews
Guest favourite
Tiny home in Winchester
The Overlook: A Sweetwater Stay
2 beds
8–13 Apr
4.98 out of 5 average rating, 64 reviews
Superhost
Cottage in Winchester
Cozy lakefront cottage on Forest Lake
4 beds
1–6 Apr
4.89 out of 5 average rating, 18 reviews
Guest favourite
Flat in Winchester
Beautiful lake side getaway, quiet.
3 beds
1–6 Apr
4.74 out of 5 average rating, 39 reviews
Superhost
Home in Winchester
Firefly Cottage: A Sweetwater Stay
3 beds
6–11 May
Guest favourite
Flat in Vernon
Farm land view.
1 queen bed
1–6 Apr
4.96 out of 5 average rating, 130 reviews
Guest favourite
Home in Swanzey
Hillside Haven: Luxe Farm Escape | 5BR-2 King Beds
7 beds
12–17 Apr
4.95 out of 5 average rating, 19 reviews
Superhost
Cottage in Warwick
By Still Waters Cottage
5 beds
1–6 Apr
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Ashuelot
Historic Home on River Covered Bridge Views
4 beds
1–6 Sep
4.98 out of 5 average rating, 86 reviews
Guest favourite
Cottage in Bernardston
Cozy, Quiet Cottage on Country rd 2 mil from I-91
2 beds
14–19 Apr
4.88 out of 5 average rating, 282 reviews
Guest favourite
Home in Chesterfield
Charming Country Home
3 beds
1–6 Apr
4.97 out of 5 average rating, 225 reviews
Guest favourite
Cabin in Fitzwilliam
Cozy Log Cabin Mountain Views
3 beds
1–6 Apr
4.85 out of 5 average rating, 106 reviews
Home in Townshend
Yellowstone in Vermont…
6–11 Apr
New place to stay