Search results; Over 1,000 places in Winchester

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Guest favorite
Home in Winchester
Winchester House with wifi/high speed internet.
8 guests4 bedrooms6 beds2 baths
May 15 – 21
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May 15 – 21
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ﺩ.ﺇ7,060 for 6 nights
for 6 nights

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Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
May 18 – 23
ﺩ.ﺇ1,959 for 5 nights
for 5 nights
4.93 out of 5 average rating, 84 reviews
Superhost
Apartment in Winsted
Haven at Highland lake
Free cancellation
Jun 1 – 6
ﺩ.ﺇ1,938 for 5 nights
for 5 nights
4.88 out of 5 average rating, 97 reviews
Top guest favorite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
May 18 – 23
ﺩ.ﺇ2,555 for 5 nights
for 5 nights
4.96 out of 5 average rating, 141 reviews
Guest favorite
Apartment in Winchester
Gateway to the Berkshires
Free cancellation
May 18 – 23
ﺩ.ﺇ2,368 for 5 nights
for 5 nights
4.91 out of 5 average rating, 376 reviews
Guest favorite
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
May 18 – 23
ﺩ.ﺇ3,229 for 5 nights
for 5 nights
4.89 out of 5 average rating, 36 reviews
Home in Winsted
Renovated lake house, just steps to the water.
Free cancellation
Jun 23 – 28
ﺩ.ﺇ4,094 for 5 nights
for 5 nights
4.63 out of 5 average rating, 24 reviews
Guest favorite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
4 beds
May 13 – 18
ﺩ.ﺇ4,563 for 5 nights
for 5 nights
5.0 out of 5 average rating, 9 reviews
Superhost
Cottage in Winsted
Cottage Ease.
2 beds
Jun 8 – 13
ﺩ.ﺇ4,304 for 5 nights
for 5 nights
4.89 out of 5 average rating, 36 reviews
Apartment in Winsted
“Hidden Gem | Fully Private ”
2 queen beds
May 19 – 24
ﺩ.ﺇ3,194 for 5 nights
for 5 nights
4.69 out of 5 average rating, 13 reviews
Apartment in Winsted
Peaceful country getaway from the hectic city life
2 beds
May 15 – 20
ﺩ.ﺇ3,186 for 5 nights
for 5 nights
4.79 out of 5 average rating, 43 reviews
Guest favorite
Home in Barkhamsted
3BR Family friendly home in Riverton paradise
Free cancellation
Jul 22 – 27
ﺩ.ﺇ4,951 for 5 nights
for 5 nights
4.94 out of 5 average rating, 17 reviews
Guest favorite
Tiny home in New Hartford
West Hill Outpost
Free cancellation
May 28 – Jun 2
ﺩ.ﺇ2,996 for 5 nights
for 5 nights
4.92 out of 5 average rating, 49 reviews
Top guest favorite
Apartment in Simsbury
Ensign House Room
Free cancellation
May 27 – Jun 1
ﺩ.ﺇ3,134 for 5 nights
for 5 nights
4.99 out of 5 average rating, 332 reviews
Top guest favorite
Home in Winsted
Lake House- Great for Families
7 beds
May 26 – 31
ﺩ.ﺇ8,555 for 5 nights
for 5 nights
5.0 out of 5 average rating, 51 reviews
Top guest favorite
Apartment in Canaan
West Main
2 queen beds
May 14 – 19
ﺩ.ﺇ2,476 for 5 nights
for 5 nights
4.99 out of 5 average rating, 139 reviews
Guest favorite
Room in Norfolk
Stay with KatharinePublic health,
Village House Hideaway
May 30 – Jun 4
ﺩ.ﺇ1,722 for 5 nights
for 5 nights
4.95 out of 5 average rating, 102 reviews
Guest favorite
Room in Canton
Stay with TannaOffice manager,
Cozy Canton - Room 1 of 2 "Sage" in our Home
May 23 – 28
ﺩ.ﺇ1,313 for 5 nights
for 5 nights
4.9 out of 5 average rating, 29 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
3 beds
May 24 – 29
ﺩ.ﺇ3,336 for 5 nights
for 5 nights
4.89 out of 5 average rating, 94 reviews