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Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Guest favorite
Guest favorite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$225
$113
night
$113 per night, originally $225
4.95 out of 5 average rating, 55 reviews
4.95 (55)
Guest favorite
Guest favorite
Home in Winsted
Lake House- Great for Families
7 beds
7 beds
Apr 20 – 25
Apr 20 – 25
$294
$244
night
$244 per night, originally $294
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favorite
Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
1 bed
Apr 20 – 25
Apr 20 – 25
$94
night
$94 per night
4.94 out of 5 average rating, 36 reviews
4.94 (36)
Guest favorite
Guest favorite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
6 beds
Apr 21 – 26
Apr 21 – 26
$250
night
$250 per night
4.94 out of 5 average rating, 196 reviews
4.94 (196)
Apartment in Winsted
Peaceful country getaway from the hectic city life
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$120
night
$120 per night
4.89 out of 5 average rating, 37 reviews
4.89 (37)
Superhost
Superhost
Cottage in Winsted
Cottage Ease.
2 beds
2 beds
Apr 25 – 30
Apr 25 – 30
$180
night
$180 per night
4.88 out of 5 average rating, 16 reviews
4.88 (16)
Superhost
Superhost
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
3 beds
3 beds
Apr 20 – 25
Apr 20 – 25
$200
night
$200 per night
Guest favorite
Guest favorite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4 beds
4 beds
Jun 23 – 28
Jun 23 – 28
$150
night
$150 per night
5.0 out of 5 average rating, 83 reviews
5.0 (83)
Apartment in Winsted
Haven at Highland lake
2 beds
2 beds
May 14 – 19
May 14 – 19
$95
night
$95 per night
4.85 out of 5 average rating, 60 reviews
4.85 (60)
Guest favorite
Guest favorite
Apartment in Winchester
Gateway to the Berkshires
2 beds
2 beds
Apr 28 – May 3
Apr 28 – May 3
$100
night
$100 per night
4.91 out of 5 average rating, 340 reviews
4.91 (340)
Superhost
Superhost
Home in Winsted
Newly renovated lakefront home!
7 beds
7 beds
Apr 22 – 27
Apr 22 – 27
$457
night
$457 per night
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Superhost
Superhost
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$132
night
$132 per night
4.87 out of 5 average rating, 30 reviews
4.87 (30)
Home in Winsted
Beecher Pond Idyll
5 beds
5 beds
Jul 14 – 19
Jul 14 – 19
$300
night
$300 per night
Guest favorite
Guest favorite
Cabin in New Hartford
West Hill Cabin
4 beds
4 beds
May 8 – 13
May 8 – 13
$224
$185
night
$185 per night, originally $224
5.0 out of 5 average rating, 33 reviews
5.0 (33)
Guest favorite
Guest favorite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a lake beach!
3 queen beds
3 queen beds
Apr 20 – 25
Apr 20 – 25
$225
$203
night
$203 per night, originally $225
4.97 out of 5 average rating, 29 reviews
4.97 (29)
Guest favorite
Guest favorite
Home in Winsted
Luxury Highland Lake Waterfront
11 beds
11 beds
Apr 21 – 26
Apr 21 – 26
$1,000
night
$1,000 per night
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Superhost
Superhost
Guesthouse in Winchester
Year-round Lakefront Highland Lake - Immaculate
4 beds
4 beds
Apr 20 – 25
Apr 20 – 25
$225
night
$225 per night
4.97 out of 5 average rating, 59 reviews
4.97 (59)
Guest favorite
Guest favorite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 beds
3 beds
May 1 – 6
May 1 – 6
$270
night
$270 per night
4.99 out of 5 average rating, 201 reviews
4.99 (201)
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