Search Winsted Cottages

"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"

"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"

"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"

"The cabin was just what we needed to escape the hustle and bustle of work!! Just the right size to sit and relax by the water and enjoy an early morning or late evening canoe ride while the Eagle flew above us. Perfect spot for day hikes or day drinking at the wineries. Then enjoy a bonfire with a glass of wine and talk about all you did and what you want to do the next day!! Definitely recommend and will be back"

"Visited a local winery, Distillary & Ice Cream shop! Ate at Salt Water Grille, Met up with extended family from Mass."

"Had a wonderful stay. Great location for our visit to my son’s school."

"Loved our time at this cozy cottage by the lake!! Beautiful views and great antique decor in the cottage!!"

"Quaint cabin tucked away in the Berkshires. For those vacationing with a pet, be aware that on Labor Day weekend this neighborhood puts on a fireworks show right by this house. Also, there really is not any yard, just a small patio. Lots of great hiking in the area."

"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."

"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."

"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...

"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...

"happen to get beautiful weather while staying at the cottage at highland lake. so nice to wake up with a view, and then at sunset to enjoy the glass like water."

"Really nice place and everything was as expected. Good location with access to all Litchfield County has to offer."

"Even with horrible weather, we had a wonderful stay!"

"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."

"Door code invalid as relayed. Check in time not honored. Upon entry thermostat read 41degrees on a a damp cold day. Multiple diffusers, plug-ins did not offset the dirty diaper, blood stained sheet, & foul bathroom smell. Meager linen supply, lack of detergent, rodent bags rounded out this thoroughly unpleasant experience."

"House was just right for our needs . Very comfortable ,clean, and private. We were in the area for family weekend at Kent School, wish we had more time to spend at the home and enjoy the great outdoors with the fall foliage and the nice outdoor fireplace. would definitely stay here again.."

"Amazing view. Great price. Great communication."

"Very positive."

"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"