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Over 1,000 places in Winsted

Guest favorite

Apartment in Winsted

Getaway for a weekend! Close to Ski Sundown.

1 bed

Apr 20 – 25

$94 per night

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

$150 per night

5.0 out of 5 average rating, 83 reviews

Guest favorite

Guest suite in Winchester

Private Suite 2 Bedroom Deck Lake Views

2 beds

Apr 21 – 26

$113 per night, originally $225

4.95 out of 5 average rating, 55 reviews

Apartment in Winsted

Haven at Highland lake

2 beds

May 14 – 19

$95 per night

4.85 out of 5 average rating, 60 reviews

Guest favorite

Home in Winsted

Lake House- Great for Families

7 beds

Apr 20 – 25

$244 per night, originally $294

5.0 out of 5 average rating, 30 reviews

Apartment in Winsted

Peaceful country getaway from the hectic city life

2 beds

Apr 21 – 26

$120 per night

4.89 out of 5 average rating, 37 reviews

Superhost

Cottage in Winsted

Cottage Ease.

2 beds

Apr 25 – 30

$180 per night

4.88 out of 5 average rating, 16 reviews

Superhost

Cottage in Winsted

Waterfront Cottage at Highland Lake w/dock

3 beds

Apr 20 – 25

$200 per night

Home in Winsted

Spacious & serene house in Berkshires

5 beds

May 8 – 13

$350 per night

Superhost

Apartment in Winsted

1st Floor The Inn at Highland Lake

2 beds

Apr 21 – 26

$132 per night

4.87 out of 5 average rating, 30 reviews

Superhost

Home in Winsted

Newly renovated lakefront home!

7 beds

Apr 22 – 27

$457 per night

4.89 out of 5 average rating, 9 reviews

Guest favorite

Home in Winsted

Luxury Highland Lake Waterfront

11 beds

Apr 21 – 26

$1,000 per night

5.0 out of 5 average rating, 9 reviews

Guest favorite

Vacation home in Torrington

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

1 queen bed

May 3 – 8

$137 per night, originally $153

4.97 out of 5 average rating, 131 reviews

Superhost

Guesthouse in Winchester

Year-round Lakefront Highland Lake - Immaculate

4 beds

Apr 20 – 25

$225 per night

4.97 out of 5 average rating, 59 reviews

Home in Winsted

Beecher Pond Idyll

5 beds

Jul 14 – 19

$300 per night

Guest favorite

Cabin in Colebrook

Adorable, storybook log cabin

6 beds

Apr 21 – 26

$250 per night

4.94 out of 5 average rating, 196 reviews

Guest favorite

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

3 beds

May 1 – 6

$270 per night

4.99 out of 5 average rating, 201 reviews

Guest favorite

Cabin in Harwinton

Beautiful Brook-side Log Cabin on 3 Private Acres

2 queen beds

Apr 21 – 26

$173 per night

5.0 out of 5 average rating, 18 reviews