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Compare 304 Vacation Homes in Canaan with updated reviews, rates, and availability.

"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"

"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."

"This was our second group visit to the Berkshire Farm House, and we plan to go back again! That fact says it all. "

"Amazing view!!!They thought of everything even things we didn’t think we wanted, right down to little things like motion sensing lights in the bathrooms. I’m a chef and cooked for my friends and I was surprised they had everything I needed. We are looking forward to coming back for another stay."

"We made happy memories over a cold January weekend. We cooked together, sat around the fire, played games and dozed in comfortable beds with high quality linens. We enjoyed the view of the water and the twinkling lights on the property at night. The steam shower was divine. If you like cooking, bring good knives, a veggie peeler and good pans. Plenty of glassware and dishes and some cookware provided. "

"Well located and comfortable "

SAR 1,291 total

includes taxes & fees

31 Jan - 1 Feb

"Nice and cozy property. The host has been very responsive. "

"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...

Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."

"Beautiful, well-stocked home with a lovely lake view. "

"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "

"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."

"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "

"Superb location in town with charm galore . Perfect spot for our 3 day weekend in the Berkshire’s An excellent enjoyable stay !"

"This was our fourth stay at this magnificent property and we continue to be amazed by its beauty and grandeur. Our host have provided us with everything to make our experience perfect. The house is well equipped and well-maintained. I would highly recommend this rental for a first-class experience. Thank you to George and Caitlin for their hospitality and kindness.."

"house is clean, well maintained, and well stocked. Owners very responsive."

"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...

"Bright, spacious and clean house on a hill. Prompt and helpful host. "

"House was comfortable and close to Butternut, catamount, and town. "

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Other property types in Canaan

"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"