Photo by Kim Knox Beckius

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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare Chalets in Winsted with updated reviews, rates, and availability.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Main level open space (old setup)

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

9.8 out of 10, Exceptional, (23)
"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Little Longbow Lakefront Chalet
Aerial view

Little Longbow Lakefront Chalet

9.2 out of 10, Wonderful, (10)
"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "
Little Longbow Lakefront Chalet
Cozy Sharon Chalet Lake House
Living area

Cozy Sharon Chalet Lake House

Cozy Sharon Chalet Lake House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winsted

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beautiful 5BR Lake House on Highland Lake

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

10.0 out of 10, Exceptional, (91)
"The house exceeded all out expectations. Beautiful, convenient to services, stunning location on the lake, plenty of off street parking. The host and I spoke multiple times throughout the stay regarding small things like trash and recycling expectations, etc."
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Family House On Highland Lake with Dock
Front of home

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (24)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.