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Search results; Over 1,000 places in Winchester

Home in Winsted
Newly renovated lakefront home!
7 beds
Apr 1 – 6
4.89 out of 5 average rating, 9 reviews
Guest favorite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4 beds
Apr 17 – 22
5.0 out of 5 average rating, 79 reviews
Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
Apr 1 – 6
4.94 out of 5 average rating, 34 reviews
Superhost
Apartment in Winsted
Haven at Highland lake
2 beds
Apr 8 – 13
4.85 out of 5 average rating, 60 reviews
Guest favorite
Home in Winsted
Lake House- Great for Families
7 beds
Apr 11 – 16
5.0 out of 5 average rating, 28 reviews
Guest favorite
Apartment in Winchester
Gateway to the Berkshires
2 beds
Apr 12 – 17
4.91 out of 5 average rating, 338 reviews
Superhost
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
Apr 7 – 12
4.87 out of 5 average rating, 30 reviews
Guest favorite
Guesthouse in New Hartford
Litchfields West Hill New Hartford Four Season BNB
3 beds
Apr 14 – 19
4.86 out of 5 average rating, 79 reviews
Guest favorite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
Apr 1 – 6
4.94 out of 5 average rating, 51 reviews
Apartment in Winsted
Peaceful country getaway from the hectic city life
2 beds
Apr 1 – 6
4.89 out of 5 average rating, 36 reviews
Guest favorite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a lake beach!
3 queen beds
Apr 7 – 12
4.96 out of 5 average rating, 27 reviews
Superhost
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
3 beds
Apr 7 – 12
Guest favorite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
Apr 1 – 6
4.94 out of 5 average rating, 196 reviews
Guest favorite
Home in Winchester
Winchester House with wifi/high speed internet.
6 beds
Apr 1 – 7
4.87 out of 5 average rating, 23 reviews
Guesthouse in Winchester
Year-round Lakefront Highland Lake - Immaculate
4 beds
Apr 1 – 6
4.97 out of 5 average rating, 59 reviews
Guest favorite
Room in Barkhamsted
Stay with JudithHosting for 8 years,
Sweet Suite in Lakefront Chalet-pvt bath
Apr 1 – 6
4.89 out of 5 average rating, 123 reviews
Home in Winsted
Beecher Pond Idyll
5 beds
Jul 14 – 19
Guest favorite
Cabin in New Hartford
West Hill Cabin
4 beds
Apr 10 – 15
5.0 out of 5 average rating, 33 reviews