Search results; Over 1,000 places in Winchester

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Guest favorite
Apartment in Winchester
Gateway to the Berkshires
6 guests1 bedroom3 beds1 bath
May 6 – 11
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May 6 – 11
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ﺩ.ﺇ 2,497 for 5 nights
for 5 nights

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Superhost
Apartment in Winsted
Haven at Highland lake
Free cancellation
May 18 – 23
ﺩ.ﺇ 1,938 for 5 nights
for 5 nights
4.88 out of 5 average rating, 96 reviews
Top guest favorite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
May 11 – 16
ﺩ.ﺇ 2,310 for 5 nights
for 5 nights
4.96 out of 5 average rating, 138 reviews
Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
May 18 – 23
ﺩ.ﺇ 2,281 for 5 nights
for 5 nights
4.93 out of 5 average rating, 83 reviews
Home in Winsted
Renovated lake house, just steps to the water.
4 beds
May 11 – 16
ﺩ.ﺇ 3,660 for 5 nights
for 5 nights
4.65 out of 5 average rating, 23 reviews
Guest favorite
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
May 6 – 11
ﺩ.ﺇ 3,229 for 5 nights
for 5 nights
4.89 out of 5 average rating, 35 reviews
Guest favorite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
4 beds
May 6 – 11
ﺩ.ﺇ 4,563 for 5 nights
for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Winsted
Lake House- Great for Families
7 beds
May 6 – 11
ﺩ.ﺇ 6,570 for 5 nights
for 5 nights
5.0 out of 5 average rating, 50 reviews
Guest favorite
Home in Winchester
Winchester House with wifi/high speed internet.
6 beds
May 10 – 16
ﺩ.ﺇ 7,060 for 6 nights
for 6 nights
4.88 out of 5 average rating, 26 reviews
Apartment in Winsted
“Hidden Gem | Fully Private ”
2 queen beds
May 8 – 13
ﺩ.ﺇ 3,256 for 5 nights
for 5 nights
4.64 out of 5 average rating, 11 reviews
Superhost
Cottage in Winsted
Cottage Ease.
2 beds
Jun 3 – 8
ﺩ.ﺇ 4,304 for 5 nights
for 5 nights
4.89 out of 5 average rating, 35 reviews
Apartment in Winsted
Peaceful country getaway from the hectic city life
2 beds
May 7 – 12
ﺩ.ﺇ 3,186 for 5 nights
for 5 nights
4.79 out of 5 average rating, 43 reviews
Top guest favorite
Farm stay in West Simsbury
Flamig Farm Staycation
Free cancellation
May 14 – 19
ﺩ.ﺇ 3,594 for 5 nights
for 5 nights
4.96 out of 5 average rating, 482 reviews
Guest favorite
Room in Norfolk
Stay with Katharine
Village House Hideaway
May 6 – 11
ﺩ.ﺇ 1,938 for 5 nights
for 5 nights
4.95 out of 5 average rating, 102 reviews
Top guest favorite
Room in Simsbury
Stay with IekeBookkeeper,
Notch Farm
May 26 – 31
ﺩ.ﺇ 3,143 for 5 nights
for 5 nights
4.95 out of 5 average rating, 40 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
3 beds
May 24 – 29
ﺩ.ﺇ 3,336 for 5 nights
for 5 nights
4.89 out of 5 average rating, 93 reviews
Guest favorite
Tiny home in New Hartford
West Hill Outpost
Free cancellation
May 28 – Jun 2
ﺩ.ﺇ 3,086 for 5 nights
for 5 nights
4.92 out of 5 average rating, 49 reviews
Guest favorite
Guest suite in East Granby
Staying at Ten Hillcrest
1 queen bed
May 11 – 16
ﺩ.ﺇ 1,722 for 5 nights
for 5 nights
4.85 out of 5 average rating, 352 reviews
Guest favorite
Apartment in Goshen
Apartment in Norfolk, CT
2 beds
May 7 – 12
ﺩ.ﺇ 3,702 for 5 nights
for 5 nights
5.0 out of 5 average rating, 28 reviews