A tractor up a tree! And, there's a picnic table underneath.

Search Vacation Homes in Winsted

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

6 Jum. II - 8 Jum. II

In two weeks

13 Jum. II - 15 Jum. II

In one month

27 Jum. II - 29 Jum. II

In two months

25 Raj. - 27 Raj.

Compare 320 Vacation Homes in Winsted with updated reviews, rates, and availability.

"The host was great and the property had everything we wanted and more. We will be back."

"Near Jacob's Pillow!"

"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."

Fridge, stovetop, dishwasher, coffee/tea maker

"Everything was as described and updated we enjoyed our stay. "

"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "

"Loved our stay at this adorable ranch home. Cute and comfy and clean. "

"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"

"This was a clean, quiet spot for a nice weekend getaway. "

"We had a wonderful wknd and the hosts thought of everything, kids had a great time and look forward to coming back."

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

SAR 2,173 total

includes taxes & fees

1 Jun - 2 Jun

"Comfortable and relaxing spot. Really pretty lake. Fun stuff for paddling around the lake."

"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "

"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "

"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"

"We really enjoyed being able to stay at such a beautiful home. Between the animals and the hot tub view - the serenity will be hard to match elsewhere!"

"Amazing view!!!They thought of everything even things we didn’t think we wanted, right down to little things like motion sensing lights in the bathrooms. I’m a chef and cooked for my friends and I was surprised they had everything I needed. We are looking forward to coming back for another stay."

"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "

"Went there for a weekend with a friend to hole up and relax in February and it was lovely. Listing is accurate and Cindy was very easy to communicate with. Hot tub was great!"