Photo by Kim Knox Beckius

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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 1 Resorts in Winsted with updated reviews, rates, and availability.

Lakeview Cottage with Dock, Kayaks
Fireplace

Lakeview Cottage with Dock, Kayaks

9.6 out of 10, Exceptional, (15)
"Great place to stay and a really great owner. Setting is outstanding and the cabins are very clean and well maintained. We will definitely go back!!"
Lakeview Cottage with Dock, Kayaks
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!
Beach

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

10.0 out of 10, Exceptional, (92)
"The spacious house and view of the frozen lake were wonderful for our family gathering. It was unfortunate the hot tub was broken and there were some water issues, but the hostess was gracious in trying to accommodate us. "
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (15)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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.

Frequently asked questions

What is Winsted like for a resort vacation?
Longing for a relaxing getaway? You deserve all the comforts of a resort, where you can find everything you want for your vacation from tasty food and drink options to activities and shopping. Browse the resort options in the area and discover the best one for you, whether you envision yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.
What's a favorite resort in Winsted?
Our top-rated resort near Winsted: Lakeview Cottage with Dock, Kayaks - 17.3 mi (27.8 km) from Winsted.
What can I do in Winsted?
Discover the shopping possibilities at Ledgebrook Plaza, or bring the kids to Flamig Farm for some family fun. For more to see in the area, you can spend time at Highland Lake or Burr Pond State Park.
What's the weather like in Winsted?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winsted are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Winsted?
Fly into Bradley Intl. Airport (BDL), which is located 19.3 mi (31 km) away from the city center. You can also search for flights into Westfield, MA (BAF-Barnes Municipal), which is 24.5 mi (39.4 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.