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Search results; Over 1,000 places in Winchester

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Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
20–25 Apr
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in Winsted
Lake House- Great for Families
7 beds
20–25 Apr
5.0 out of 5 average rating, 30 reviews
Guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
Individual Host
21–26 Apr
4.95 out of 5 average rating, 55 reviews
Guest favourite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4 beds
23–28 Jun
5.0 out of 5 average rating, 83 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
Individual Host
28 Apr – 3 May
4.91 out of 5 average rating, 340 reviews
Superhost
Cottage in Winsted
Cottage Ease.
2 beds
25–30 Apr
4.88 out of 5 average rating, 16 reviews
Superhost
Home in Winsted
Newly renovated lakefront home!
7 beds
22–27 Apr
4.89 out of 5 average rating, 9 reviews
Flat in Winsted
Haven at Highland lake
2 beds
14–19 May
4.85 out of 5 average rating, 60 reviews
Guest favourite
Cabin in Colebrook
Adorable, storybook log cabin
Individual Host
21–26 Apr
4.94 out of 5 average rating, 196 reviews
Guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
11 beds
21–26 Apr
5.0 out of 5 average rating, 9 reviews
Guest favourite
Room in Barkhamsted
Stay with JudithHosting for 8 years,
Sweet Suite in Lakefront Chalet-pvt bath
20–25 AprIndividual Host,
4.89 out of 5 average rating, 124 reviews
Superhost
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
Individual Host
19–24 Apr
Flat in Winsted
Peaceful country getaway from the hectic city life
Individual Host
21–26 Apr
4.89 out of 5 average rating, 37 reviews
Superhost
Flat in Winsted
2nd Floor The Inn at Highland Lake
Individual Host
19–24 Apr
4.87 out of 5 average rating, 38 reviews
Guest favourite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a lake beach!
3 queen beds
20–25 Apr
4.97 out of 5 average rating, 29 reviews
Home in Winsted
Beecher Pond Idyll
5 beds
14–19 Jul
Guest favourite
Room in Norfolk
Stay with Katharine
Village House Hideaway
19–24 Apr
4.96 out of 5 average rating, 78 reviews
Guest favourite
Cabin in New Hartford
West Hill Cabin
4 beds
8–13 May
5.0 out of 5 average rating, 33 reviews