Vacation rentals in Canaan

If you're thinking about booking Kristen's Chalet - do not hesitate! Book it - you won't be disappointed. The house has ample room to spread out with your family. We enjoyed our Christmas dinner at the dining table and afterwards, we were able to watch a movie together. The location was perfect for us to go out every day and explore - Red Lion Inn, The Mount and several other towns. We had to make plans to stay in so we could enjoy the beautiful Chalet for an evening. We can not wait to return and enjoy this beautiful home. ♡

The cabin is really cute. They have everything you could need there. I really loved the screened in lanai. My husband and I stayed for a long weekend with our dogs. Everyone we ran into was friendly and respectful. It’s the prefect place for a quiet getaway. The lake is so clear and it was so nice to take a dip to escape the hot weather. The lake beach is not pet friendly but there are plenty of places that are. There are several trails that allow dogs and the orchard up the road also allows dogs just to name a few. We really enjoyed our stay. It’s a great area to recharge.

Wonderful home and grounds, quaint and eclectic decor. Super comfortable beds and right-at-home warmth. Responsive, friendly hosts!

Thank you Becky for a wonderful stay. The house was very comfortable and the gardens were gorgeous. Our family of four stayed here for a family wedding in the Berkshires. The kitchen was well appointed for cooking and cozy for hanging out during down time. The beds were exceptionally comfortable. Unfortunately it was cold and cloudy so we did not go swimming, but we did stop by and look at the private beach which is charming. A perfect place to spend some summer hours, especially if you have kids. Bob and Becky were attentive, considerate hosts, and they took care to alert us to the quirks of the house. This is their regular home, so it’s old-school Airbnb, not a sterile hotel-room-ish property. We felt welcomed and we enjoyed our stay very much.

Katie's home in Great Barrington was a lovely cottage nestled among greenery. We appreciated its cozy and modern design and very nice details like the Aesop soap. The location was very central in the Berkshires area. Just a short drive to Stockbridge main street, and a nice 15 minute drive to Tanglewood. Katie sent detailed instructions making it easy to find and enter the house and responded quickly to questions. The cottage is close to the main house, but it was very private inside with the landscaping around and excellent shades. The residential road definitely made it feel like a weekend in the country.

We had a truly magical stay at this cozy A-frame! Everything was spotless when we arrived, and the bed was incredibly comfortable—perfect for sinking into after a day outdoors. The hosts were super responsive and helpful throughout our visit. We loved making dinner on the front deck both nights and then relaxing under the stars. Watching fireflies and even catching a couple of shooting stars made the evenings feel perfect. Even on warm, sunny days, the A-frame cooled off beautifully once we opened the doors before bed—perfect for a restful night’s sleep. This was exactly the kind of glamping experience we were hoping for. The cabin had a few basics like plates, utensils, and a cast iron pan, but we brought some of our own supplies just in case. Our pup was comfy and happy too—we kept her leashed since there are other dogs on the property, but it all worked out great. Such a beautiful spot with a peaceful atmosphere. We’d absolutely come back!

We had an amazing stay at this beautiful getaway! The highlight was definitely the stunning deck – perfect for relaxing with a morning coffee. The hot tub was such a treat and made the peaceful, private location feel like a true escape. The home was exactly as pictured – clean, cozy, and thoughtfully furnished. The beds were super comfortable, and everything we needed was provided. The views were great! The only small downside was the lack of air conditioning during a couple of unexpectedly hot days, but with fans and cool evenings, we were still comfortable. Overall, a wonderful experience and one we’d love to repeat. Highly recommended for anyone looking to unwind and enjoy nature in comfort!

It's a good value in a quiet neighborhood. Sure, the nearby train and traffic from the main road can be a little unpleasant, and the spotty cell service isn't ideal. But the place itself is great for cooking meals, cleaning up, and getting some good rest. Also with it being two floors and well spread out it felt very spacious, but still cozy on rainy days. The only downside were the few ants who wandered the kitchen while I was there, but they mostly kept to themselves. All in all, I'd gladly stay here again with my pup.