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Winchester
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Over 1,000 places in Winchester
Guest favorite
Guest favorite
Tiny home in Winchester
The Overlook: A Sweetwater Stay
2 beds
2 beds
May 11 – 16
May 11 – 16
$113
night
$113 per night
4.98 out of 5 average rating, 65 reviews
4.98 (65)
Guest favorite
Guest favorite
Cottage in Winchester
Storybook Lake Front Villa with Private Beach!
4 beds
4 beds
May 1 – 6
May 1 – 6
$279
night
$279 per night
4.93 out of 5 average rating, 27 reviews
4.93 (27)
Guest favorite
Guest favorite
Apartment in Winchester
Downtown Loft above Winery and Distillery
1 double bed
1 double bed
Apr 26 – May 1
Apr 26 – May 1
$82
night
$82 per night
4.93 out of 5 average rating, 162 reviews
4.93 (162)
Guest favorite
Guest favorite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
May 11 – 16
May 11 – 16
$136
night
$136 per night
4.86 out of 5 average rating, 59 reviews
4.86 (59)
Guest favorite
Guest favorite
Vacation home in Winchester
Lakefront Elegance with your own private beach
2 beds
2 beds
May 5 – 10
May 5 – 10
$218
night
$218 per night
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favorite
Guest favorite
Guesthouse in Winchester
The Higgle House: A Sweetwater Farm Stay
2 queen beds
2 queen beds
Apr 20 – 25
Apr 20 – 25
$75
night
$75 per night
4.89 out of 5 average rating, 57 reviews
4.89 (57)
Superhost
Superhost
Home in Winchester
Firefly Cottage: A Sweetwater Stay
3 beds
3 beds
May 6 – 11
May 6 – 11
$77
night
$77 per night
Superhost
Superhost
Home in Winchester
Dragonfly Cottages: A Sweetwater Stay
4 beds
4 beds
Jun 3 – 8
Jun 3 – 8
$113
night
$113 per night
Guest favorite
Guest favorite
Townhouse in Winchester
Timber Frame Loft
1 queen bed
1 queen bed
May 24 – 29
May 24 – 29
$86
night
$86 per night
4.88 out of 5 average rating, 68 reviews
4.88 (68)
Guest favorite
Guest favorite
Apartment in Vernon
Farm land view.
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$95
night
$95 per night
4.96 out of 5 average rating, 132 reviews
4.96 (132)
Guest favorite
Guest favorite
Home in Ashuelot
Historic Home on River Covered Bridge Views
4 beds
4 beds
Sep 1 – 6
Sep 1 – 6
$160
night
$160 per night
4.98 out of 5 average rating, 86 reviews
4.98 (86)
Superhost
Superhost
Cottage in Winchester
Cozy lakefront cottage on Forest Lake
4 beds
4 beds
Nov 3 – 8
Nov 3 – 8
$300
night
$300 per night
4.89 out of 5 average rating, 18 reviews
4.89 (18)
Guest favorite
Guest favorite
Tiny home in Brattleboro
Sweet Vermont Tiny Home Get Away
1 double bed
1 double bed
Apr 26 – May 1
Apr 26 – May 1
$88
$73
night
$73 per night, originally $88
4.94 out of 5 average rating, 34 reviews
4.94 (34)
Guest favorite
Guest favorite
Cottage in Bernardston
Cozy, Quiet Cottage on Country rd 2 mil from I-91
2 beds
2 beds
Jun 24 – 29
Jun 24 – 29
$124
night
$124 per night
4.88 out of 5 average rating, 285 reviews
4.88 (285)
Superhost
Superhost
Cottage in Warwick
By Still Waters Cottage
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$290
night
$290 per night
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Guest favorite
Guest favorite
Home in Swanzey
Hillside Haven: Luxe Farm Escape | 5BR-2 King Beds
7 beds
7 beds
Apr 20 – 25
Apr 20 – 25
$265
$239
night
$239 per night, originally $265
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Guest favorite
Guest favorite
Guest suite in Fitzwilliam
The Great Room in Historic Fitzwilliam
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$95
night
$95 per night
4.98 out of 5 average rating, 124 reviews
4.98 (124)
Guest favorite
Guest favorite
Cottage in Orange
The Film Shack: A Sweetwater Stay
6 beds
6 beds
Apr 20 – 25
Apr 20 – 25
$150
$116
night
$116 per night, originally $150
4.96 out of 5 average rating, 74 reviews
4.96 (74)
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