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Search results; Over 1,000 places in Winchester

Guest favorite
Tiny home in Winchester
The Overlook: A Sweetwater Stay
2 beds
May 11 – 16
4.98 out of 5 average rating, 65 reviews
Guest favorite
Cottage in Winchester
Storybook Lake Front Villa with Private Beach!
4 beds
May 1 – 6
4.93 out of 5 average rating, 27 reviews
Guest favorite
Vacation home in Winchester
Lakefront Elegance with your own private beach
2 beds
May 5 – 10
5.0 out of 5 average rating, 9 reviews
Guest favorite
Apartment in Winchester
Downtown Loft above Winery and Distillery
1 double bed
Apr 26 – May 1
4.93 out of 5 average rating, 161 reviews
Guest favorite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
May 11 – 16
4.86 out of 5 average rating, 59 reviews
Guest favorite
Guesthouse in Winchester
The Higgle House: A Sweetwater Farm Stay
2 queen beds
Apr 19 – 24
4.89 out of 5 average rating, 57 reviews
Superhost
Home in Winchester
Firefly Cottage: A Sweetwater Stay
3 beds
May 6 – 11
Superhost
Home in Winchester
Dragonfly Cottages: A Sweetwater Stay
4 beds
Jun 3 – 8
Guest favorite
Townhouse in Winchester
Timber Frame Loft
1 queen bed
May 24 – 29
4.88 out of 5 average rating, 68 reviews
Guest favorite
Apartment in Vernon
Farm land view.
1 queen bed
Apr 21 – 26
4.96 out of 5 average rating, 132 reviews
Guest favorite
Home in Ashuelot
Historic Home on River Covered Bridge Views
4 beds
Sep 1 – 6
4.98 out of 5 average rating, 86 reviews
Home in Swanzey
Lake Front Cottage
2 double beds
May 29 – Jun 3
New place to stay
Superhost
Cottage in Winchester
Cozy lakefront cottage on Forest Lake
4 beds
Nov 3 – 8
4.89 out of 5 average rating, 18 reviews
Guest favorite
Apartment in Winchester
Beautiful lake side getaway, quiet.
3 beds
Apr 22 – 27
4.75 out of 5 average rating, 40 reviews
Guest favorite
Tiny home in Brattleboro
Sweet Vermont Tiny Home Get Away
1 double bed
Apr 26 – May 1
4.94 out of 5 average rating, 34 reviews
Superhost
Cottage in Warwick
By Still Waters Cottage
5 beds
Apr 20 – 25
5.0 out of 5 average rating, 19 reviews
Guest favorite
Cottage in Bernardston
Cozy, Quiet Cottage on Country rd 2 mil from I-91
2 beds
Jun 24 – 29
4.88 out of 5 average rating, 285 reviews
Guest favorite
Home in Swanzey
Hillside Haven: Luxe Farm Escape | 5BR-2 King Beds
7 beds
Apr 20 – 25
4.95 out of 5 average rating, 20 reviews