Vacation rentals with a kayak in Great Barrington

We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!

Katherine’s Creekside Cottage was a perfect peaceful getaway and I wish we could have stayed longer ! Felt at home the minute we walked through the door .. living room with electric fireplace, beautiful newly renovated kitchen with everything you need, sparkling clean bathrooms with lovely towels and the prettiest bedrooms. There are so many special touches everywhere . The weather wasn’t perfect, but we still spent hours just relaxing on the screened in porch, You won’t want to leave it! Took advantage of Katherine’s recommendations for dinner (she has quite a nice list but we choose Lucy’s Kitchen in Saugerties … just great!) and spent the day in nearby Woodstock, amazing little town. We had no issues whatsoever and almost any question you have can be addressed in the Home Manual she has available. Even so, she was super quick to answer a question I had and definitely wanted to make sure we were comfortable . Don’t hesitate to book this little gem!

Great place to stay! So open & clean with such a nice spot on the lake. With an awesome host that is very friendly & accommodating! Highly recommended a visit

Felt right at home at this cozy cottage! Pleased with the amenities, comfortable beds and great space to hang out in! Would definitely return!

The place was incredibly beautiful. The photos did not do it justice. It is in the middle of nowhere. Tina was very detailed in her instruction and one of them was that you must bring groceries because the closest grocery store is 30 minutes away. If you decide to book this place, read her detailed instructions. They are very helpful. The home offered a full kitchen which made it so easy for us to prepared our family's meals without struggling. The hot tub was such a treat. The basement had lots of games, a couch to launch and another TV. Perfect if you come with children. We were seven adults and we did not feel that we where on top of each other. The high ceiling truly made one of our boys (the giant) feel at home. Even the basement had a high ceiling. Pretty cool. Tina was incredibly nice and flexible. Check in is at 4 pm and we arrived earlier. We decided to contact her to see if it would be okay to check in earlier and she accommodated us. Thank you soooo much.

Daphne is a thoughtful and wonderful host. The property was clean, comfortable and very well appointed with everything I would need, especially in the kitchen. I highly recommend this 5-star property. It is quiet, peaceful and full of nature everywhere the eye can see.

This place was amazing. My team and I stayed here for a race weekend, and everyone loved it. There were lots of cool birds that were in the river nearby or the backyard, which made for some fun bird watching. I highly recommend!

What we needed was really just a "heads in the bed" type situation as we had plans that were to keep us away from the house most of the day but really the place was very homey and lovely to come back to. Everything was just as described. The hosts were flexible and offered early check-in/late check-out unprompted which was nice to have some time to relax the day we checked out. Overall it was a great stay!

The perfect place for a cozy getaway from the city! We really needed an R&R and this place gave us what we needed and would be happy to come back here again ✨

It's hard to beat a place like this if you are looking for a peaceful, quiet, and comfortable stay. The lakefront backyard with kayaks, fireplace, heated porch with swing, and amenities to meet any basic need, made this a wonderful base for our group of four adults, a child, and furry friend to explore the area. It's a beautiful country/lake side escape a short drive from a number of villages and towns providing great eats, good shopping, and sightseeing. Highly recommend.

I can’t say enough positive things about Daniel’s place. The setting was beautiful and serene; It was so quiet and peaceful we almost felt like it was our own private lake! The house was lovely and so tastefully and uniquely decorated. All the windows gave a constant view of the lake. There are many quaint towns to explore within a 30 minute drive, but you may want to spend most of your time enjoying the lake and kayak. We hope to return in the summer.

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!

My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.

Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.

I visited this beautiful place for valentines weekend and it was absolutely amazing, nice and clean kitchen equipped with all you need if you want to cook and the rooms were nice and cozy. Also this is a lake house so you have a beautiful view and you can enjoy outside too. We had a great time. I would only suggest to get the drive way clean from the ice/snow during winter time it was a little bit dangerous walking to our cars.

Stayed with my husband and two kids, ages 4 and 1. This place was perfect for us, and the children really enjoyed it because there were games for them to play and plenty of room to crawl around! The cabin itself is something like 750 sq feet but feels so spacious. We never felt cramped and had plenty of room to relax. All necessities were included as well as some extras like laundry detergent, aluminum foil for cooking, even cooking oil and seasonings. That’s not something I’ve typically seen in homes we’ve rented before. What absolutely impressed us were the views. We loved how there are no street lamps. After dark it feels like you really are out in the middle of nowhere, but you actually have so many restaurants and activities within a very short driving distance. Andrew was also a very welcoming host. I messaged him during our stay twice and had responses from him within minutes. I’m so glad we found this cabin and wish we find our way back to it someday!

Spent the weekend at this super cozy cabin in Palenville and loved it. Peaceful, comfy, and surrounded by nature—just what we needed. Perfect little escape from the city. Would totally come back!

What can I say except WOW! Incredible property, cabin and serene setting all packed in one Airbnb! Katrina was the perfect host answering any questions we had leading up to and during our stay. The cabin was spotless, private and exactly what we were looking for! Katrina's local recommendations were great and we also found 2 places that I thought to mention: Gracie's Luncheonette for breakfast (gotta try the hash browns!) and Red's Seafood (if you're looking for some incredible GF options). Would stay here again in a second! We were able to get to multiple hikes in, easy and moderate, within 30-45 minute drives. I highly recommend Katrina's Airbnb for a weekend getaway!

Tobye’s place was the perfect location for our Thanksgiving trip. Had all the amenities as listed and is a very responsive host. Was flexible to add a day as well and we so appreciated that! Kids loved the Xbox and we loved the coffee and peaceful view.

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!

We booked this trip last minute during our daughter’s spring break. It was a little under 2 hours from NYC and felt like a world away. The hosts were always available and helpful with everything down to local suggestions. Every detail of the cabin is thoughtfully laid out and provided. We slept four comfortably, but mostly spent our time outside. The property alone offers many trails to explore and made us feel entirely off the grid. The porch around the cabin had locks which would be great for young kids or pets. The surrounding towns were cute and restaurants were excellent. Everything including a supermarket seems to be 10 minutes or under, but we mainly liked staying on the property. We can’t wait to come back in warmer months to go tubing!

A charming cabin perfect for a weekend away. Our group opted mostly to stay in instead of explore local areas and it was the perfect size with just enough to do! The small explorations we did have for local coffee and produce were wonderful. A couple issues with some household appliances but the host was responsive and considerate to resolve them. Loved the doc, kayaks, and hot tub as well as smaller objects to use for entertainment, such as a guitar, fireplace, and games. Hope to come back next year!

Beautiful house! We enjoyed our stay and found the house to be very comfortable and cozy! The location was great and felt very secluded but yet still very close to town. Loved all the amenities the house had to offer and the dogs enjoyed playing in the yard. The art and records in the house were a great touch. We would love to come back again!

Great location near West Hill Lake and Brodie Park; walking distance to public beach, playground, and more. The house is very clean and well provisioned. A great stay!