Photo by Kim Knox Beckius

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 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, (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!
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (211)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake
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, (14)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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 KidsPlay Museum 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.