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Search results; Over 1,000 places in Winchester

Guest favourite
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
Guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
11 beds
Apr. 1 – 6
5.0 out of 5 average rating, 9 reviews
Home in Winsted
Newly renovated lakefront home!
7 beds
Apr. 1 – 6
4.89 out of 5 average rating, 9 reviews
Superhost
Apartment in Winsted
Haven at Highland lake
2 beds
Apr. 8 – 13
4.85 out of 5 average rating, 60 reviews
Guest favourite
Home in Winsted
Lake House- Great for Families
7 beds
Apr. 11 – 16
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4 beds
Apr. 17 – 22
5.0 out of 5 average rating, 79 reviews
Superhost
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
3 beds
Apr. 7 – 12
Superhost
Apartment in Winsted
2nd Floor The Inn at Highland Lake
6 beds
Apr. 1 – 6
4.86 out of 5 average rating, 37 reviews
Guest favourite
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
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 favourite
Home in Winchester
Winchester House with wifi/high speed internet.
6 beds
Apr. 1 – 7
4.87 out of 5 average rating, 23 reviews
Guest favourite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
Apr. 1 – 6
4.94 out of 5 average rating, 196 reviews
Home in Winsted
Beecher Pond Idyll
5 beds
Jul. 14 – 19
Guest favourite
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
Guest favourite
Cabin in New Hartford
West Hill Cabin
4 beds
Apr. 10 – 15
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 beds
Apr. 1 – 6
4.99 out of 5 average rating, 200 reviews
Guest favourite
Home in Litchfield County
70’s Retro House
2 beds
Jun. 23 – 28
4.91 out of 5 average rating, 11 reviews
Home in Winsted
New - Berkshire Spring Getaway
4 beds
Apr. 1 – 6