Vacation rentals with a kayak in The Berkshires

We loved our stay at this lakeside cottage! Quick 12 minute drive to Otis Ridge for skiing. Elle was super responsive. The house fit all our needs for two families with young kids - great space for hanging out, lots of perks for the kids, the ping pong table was a hit. We’d love to stay here again in warmer weather.

Absolutely perfect stay during a meaningful and emotional time. We came to this beautiful lakefront Airbnb to celebrate my husband’s birthday after his passing, hoping for peace and comfort—and it was everything we needed. The weather happened to be beautiful, which allowed us to take out the kayaks and fully enjoy the calm and serenity of the lake. The sunsets and sunrises were absolutely phenomenal—quiet, breathtaking moments that brought so much peace. The home itself was spotless, cozy, and incredibly well stocked with everything we could possibly need—from kitchen essentials to extra linens and thoughtful touches throughout. You can tell it’s a family-owned home, filled with warmth and very well taken care of, which made it feel even more special. It was also very family-friendly, making it a perfect fit for all of us and plenty for all to do. We truly appreciated how kind, helpful, and responsive the host was throughout our stay. We’re grateful and hope to return .

We absolutely loved our stay at the nest. The setting was perfect for a relaxing couple days for our family. Fishing, kayaking, hot tubing and walking. Jennifer was a great host ! Definitely recommend !!

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

We had a lovely time at this place, it’s a bit small but we’ll appointed and you can’t beat the location, right on the river! The views out the back were incredible every day. This didn’t impact us but be aware the upstairs loft area is probably better for children and a tall adult would feel pretty cramped up there. As a rather short crew my family had no problems 😂. Would definitely stay again.

We were looking for a place to unwind and we did with Seth’s place. Right on the river, great views, enjoyed the hot tub and very comfortable beds! We had a relaxing time.

We loved our late winter stay on the lake - it was very peaceful and we had some great bird-watching opportunities. The art and special objects in the house made for a very cozy and beautiful environment. Overall, it was very comfortable and we would definitely stay again.

From start to finish Zoe was very responsive and accommodating. The bathrooms and bedrooms were very clean and neat. The bedding was very comfortable. We cooked a dinner and a breakfast and the kitchen was stocked well enough to make both these meals easy.

It was wonderful! being lakeside with the help of the weather gods, it was PERFECT! Three decks ourside,kayaks avialable. Spectacular view ourside and from most windows inside. The resident duck tribe added to the natural beauty. Indoors, a clean, fresh feeling, comfortable furniture and beds. It was a home run as soon as we entered the door.

The place was very comfortable and could see the lake through the three windows. Very clean and cozy and would go back again.

Staying at Sonya’s house was an amazing experience! The house is very clean, updated, quiet and had everything we needed! I highly recommend staying at the cottage on the lake. The porch was an extra spot that the sun shined all day! It truly was a beautiful weekend!

Stephanie was fantastic at communication prior to our trip. Home was perfect for our stay.

If you are looking for simplicity (which we were) this is the perfect place to. I’ve always wanted to stay at a lake house. We couldn’t have asked for more. Serene, tranquil, beautiful are the proper descriptions of the house and the area. We came to Connecticut to visit my daughter and family and they ended up coming to our place instead. Jason was extremely helpful when needed. We would definitely stay there again!

An excellent stay with incredibly responsive hosts. Snowed while we were here and it was a winter wonderland. Kid friendly, quiet; a great place to reset.

We loved our stay at the cabin! It was clean, the kitchen was well stocked for cooking, and the location was beautiful. We stayed for a few days and celebrated our early family Christmas here. It ended up snowing, which made the surrounding Connecticut forest even more beautiful. We found the cabin cozy and peaceful, with the town just 10 minutes away for anything we’d need. I definitely plan to keep this listing in mind for next time I’m visiting family in Connecticut.

We had to come to the area for a family funeral, so this was a last minute booking, and Nicole was just the best. She got us in quickly, with less than 24 hours' notice. The house is absolutely beautiful, and overlooks the equally beautiful Oxoboxo Lake. Would recommend this house to anyone needing to stay in the area. Thank you Nicole!

Jill’s home was a perfect escape from city life. You might lose cell service but it felt great to unplug from a busy schedule. Jill leaves a book of towns, trails and activities to check that was very helpful when my group wanted to leave the house and explore the towns a bit. Definitely would love to come again in the summer to enjoy the lake access.

This was our 2nd time staying at Brian's place, the home is perfect for a larger group and has so many toys for the kids, they LOVED it! Everything is very clean, and the kitchen has all the pots/pans needed for cooking. In Feb there was so much snow we got to go sledding in the front yard, and a few from our group made the trip to Stratton for the day. We love going to Wilmington for coffee/lunch. Planning to be back again in 2026!

This place was so peaceful and gorgeous! We stayed here during the A Weekend in the Life event and it was such an easy drive into town and to all the activities. The house itself had great amenities and things to do! During our stay, the heater did break, but our host was on top of it. The house has a pellet stove that kept it toasty, so she had 5 bags of pellets delivered to the house for us, she had someone come out and service the pellet stove and she had someone come out to service the heat all in one day! They were accommodating and helpful. We also had our dogs with us who has plenty of space and the airbnb didn’t smell like dog. You couldn’t tell it was a pet friendly place. We loved it!

This place was perfect for a peaceful weekend getaway. On the chilly fall weekend the wood stove and sauna were much enjoyed. We hope to return!

We loved our stay at Ed's cabin. it is a real gem and perfect for a long weekend away. we loved the fireplace, the rocking chairs, the windows with views out onto the lake that make you feel like you're right over the lake and in the trees. there were nice restaurants and hikes in the area, but we were perfectly content watching the lake and reading from the cabin. Ed was perfectly accommodating and extremely generous with his space, couldn't recommend more highly.

We had an amazing weekend stay at Catherine and Diego’s modern cabin! The property is exactly as described—beautiful, cozy, and perfect for a group getaway, with charming wood paneling and all the comforts of home. The hot tub and stunning views of the snow-covered landscape were highlights, creating a peaceful and relaxing atmosphere after a day out. The location was ideal, offering both privacy and proximity to skiing and other activities, and the hosts provided clear instructions for check-in, making the experience stress-free. We’d highly recommend this cabin to anyone looking for a quiet, cozy escape in the mountains!

Dasha was incredibly helpful, especially since it was very snowy and we had trouble getting in and out of the driveway. Lovely secluded cabin, well appointed kitchen, nice area to hike around, very dog friendly.

This is the perfect cabin retreat. Beautiful property with incredible back porch views, stunning fireplace, creekside access, and gobbling turkeys in the distance. It was just what I was looking for to celebrate a birthday with friends. Secluded enough to feel private but close enough to a charming town for drinks and coffee. Jim was also super communicative and made it easy to settle in—he even gave me a heads up about the weather that weekend to make sure we were packed appropriately. I was considering a couple of places, and I’m so happy I chose this one. Highly recommend a visit. P.S. The heated floors are a really nice touch.