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Search results; Over 1,000 places in Winchester

Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
Apr 20 – 25
4.94 out of 5 average rating, 36 reviews
Guest favorite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4 beds
Jun 23 – 28
5.0 out of 5 average rating, 83 reviews
Guest favorite
Home in Winsted
Lake House- Great for Families
7 beds
Apr 20 – 25
5.0 out of 5 average rating, 30 reviews
Apartment in Winsted
Haven at Highland lake
2 beds
May 14 – 19
4.85 out of 5 average rating, 60 reviews
Superhost
Cottage in Winsted
Cottage Ease.
2 beds
Apr 25 – 30
4.88 out of 5 average rating, 16 reviews
Guest favorite
Apartment in Winchester
Gateway to the Berkshires
2 beds
Apr 28 – May 3
4.91 out of 5 average rating, 340 reviews
Superhost
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
3 beds
Apr 19 – 24
Apartment in Winsted
Peaceful country getaway from the hectic city life
2 beds
Apr 21 – 26
4.89 out of 5 average rating, 37 reviews
Superhost
Home in Winsted
Newly renovated lakefront home!
7 beds
Apr 22 – 27
4.89 out of 5 average rating, 9 reviews
Superhost
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
Apr 21 – 26
4.87 out of 5 average rating, 30 reviews
Guest favorite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
Apr 21 – 26
4.94 out of 5 average rating, 196 reviews
Home in Winsted
Beecher Pond Idyll
5 beds
Jul 14 – 19
Guest favorite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a lake beach!
3 queen beds
Apr 20 – 25
4.97 out of 5 average rating, 29 reviews
Guest favorite
Home in Winsted
Luxury Highland Lake Waterfront
11 beds
Apr 21 – 26
5.0 out of 5 average rating, 9 reviews
Guest favorite
Cabin in New Hartford
West Hill Cabin
4 beds
May 8 – 13
5.0 out of 5 average rating, 33 reviews
Superhost
Guesthouse in Winchester
Year-round Lakefront Highland Lake - Immaculate
4 beds
Apr 20 – 25
4.97 out of 5 average rating, 59 reviews
Home in Winsted
Spacious & serene house in Berkshires
5 beds
May 8 – 13
Guest favorite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 queen beds
Apr 21 – 26
5.0 out of 5 average rating, 18 reviews