Holiday rentals with a kayak in The Berkshires

My family had such a wonderful time staying here. The house was spacious yet cozy and we were able to prepare a full Thanksgiving meal with everything we needed at our fingertips. The bedrooms and bathrooms are spacious and comfortable, and the surroundings are right out of a Hallmark movie. We will definitely return!

We had a wonderful long weekend at Elle’s house. The bedrooms and living spaces were thoughtfully laid out and decorated beautifully. A short drive to lots of little cafés and hiking trails. We appreciated the quiet solitude of this little getaway in the Berkshires, and the ping pong table too. We didn’t get to use the lake (snow in April!) but hope to return to try again!

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 stayed here right after our wedding in Westchester county as a "mini-moon" for a couple of days and absolutely loved it! It was the perfect place to relax especially on the patio overlooking the water and the hot tub was an added bonus. This is one of the few Airbnbs we have stayed in that we would go back to in a heartbeat. Beautiful!!! Highly recommend :)

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.

I loved staying here! My boyfriend and I would definitely come back!

Thanks for much for an amazing stay! Sonya took extra steps to ensure we enjoyed our time here. It was a cozy little cottage and the perfect little getaway. We will be back!

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

We came up to Joan's lovely cottage for a peaceful, hiking Christmas vaca and it was absolutely perfect. Joan was a wonderful host, very friendly and generous. We wish Joan was our granny too! Granny camp was comfy, cozy, on a beautiful lake, with lots to do in surroundings areas. Would love to come back in the summer! Thank you!

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!

We had a very peaceful stay at Sleepy Loon cottage. Enjoyed the quietness and saw lots of loons, geese, ducks and even saw a beaver. It was cold and windy so didn't get to use kayaks as planned but still had a great time. Lori and Mark were great hosts. If you are looking for a quiet and relaxing place this is it! The cottage is exactly as pictured.

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!

I recently had the pleasure of staying at Dino’s Black Bear Cabin. The cabin is private and peaceful, such a nice getaway from the city. The furniture is comfortable, linens soft and kitchen fully stocked with spices and basic ingredients. Loved the unique basement speakeasy and jacuzzi. The cabin had everything we needed. The views of the lake and surrounding woods were breathtaking, providing a peaceful atmosphere to unwind. The host was exceptional—thoughtful, responsive, and always willing to help with any questions we had. Their attention to detail truly made a difference in our stay. Overall, the stay was an amazing stay. We hope to stay again and again. I would buy this place if it was for sale!! 10 out of 10 would recommend!

Ivan's place emulated a YouTube cozy winter jazz 12 hour video. It had everything you ever needed to feel relaxed and at peace. There were antique fire places inside the home, the house was made out of wood, it was clean and stylish. The location was great , facing the lake and mountains. It was a great place to disconnect and get away from all the noise. The town was 10 min away where you can get anything from wine to coffee to produce. Really grateful to the host for creating such a nourishing space and sharing it with the world. Thank you Ivan!

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!

Thank you, Jordyn! We loved your Airbnb and had so much fun!!

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!

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.