Holiday rentals with a pool in Chatham

This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!

The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

The teahouse and surroundings were relaxing and peaceful. We saw groundhogs, deer, and chipmunks from the porch and our 2 dogs loved exploring the field and wandering in the nearby woods. The pool was amazing and warm despite the rain and the natural landscaping couldn’t have been more beautiful. We really enjoyed our stay!

Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!

We loved Kathryn’s place! It was so peaceful and pretty, we loved having lake access, and it was convenient to drive to several local towns with great restaurants. The whole family enjoyed the kayaks and the community pool and the lovely outdoor space. My favorite part of the stay was the friendly fox who would visit the property in the mornings. Kathryn was also a wonderful host and responsive to our questions/messages. I would definitely stay here again!

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

I went with my friends and the house was amazing, it had beautiful views the pool and hot tub was great everyone had a great time!

Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Was as advertised. Would recommend

Great little studio spot to use as your Basecamp for activities in the area!

We stayed at Renee’s place during a summer festival weekend hosted at the mountain and it was perfect for our needs! Comfy bed, good kitchen set up and a nice place for lounging in between festival events. Would definitely stay here again!

Wonderful stay!! Very clean and cozy space. The host was easy and lovely to communicate with!