Holiday rentals with a pool in Western Massachusetts

Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

From the moment we arrived, we felt completely at home thanks to the incredibly warm and welcoming hosts, Tania and Glenn. They went above and beyond to make our stay comfortable, offering great local tips and always greeting us with a smile. Their hospitality truly made a difference. The home itself is absolutely stunning—beautifully designed, impeccably clean, and filled with thoughtful touches that made it feel extra special. Whether we were enjoying a quiet morning coffee or relaxing in the cozy living area after a day of exploring, everything was perfect. This was one of the best Airbnb experiences we've ever had. If you're lucky enough to find availability here—book it! You won't regret it. Thank you, Tania and Glenn, for a truly unforgettable stay! 💛

We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

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.

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

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.***

This was my first ever experience with AirBNB. I couldn't have stayed at a better location for my first experience! Melissa's home was warm welcoming and beautiful. I stayed for four nights with my four children. There was plenty of space for all of us. Although my youngest still chose to sleep with me lol the bed was still big enough for the two of us. The pool was absolutely perfect, my kids loved it! The hot tub was very relaxing and very easy to use. My kids really enjoyed it too. The grill worked wonderfully and the fire pit was great for smores. The covered patio made watching my kids enjoy the pool even more relaxing for me, I'm a ginger so if I can be outside and out of direct sunlight that's a huge bonus for me. The kitchen had everything we needed as well. Melissa was very responsive when I had questions and I cannot thank her enough for the great week. We'll be back next June for another week! Can't wait to return to this fantastic vacation spot!

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again

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.

You really can’t beat this location. It’s across the steet from the lifts and the village with lots of restaurants/bars/stores. The space was perfect for our family of four. Our two young children stayed on the pullout and we thought the king bed was quite comfy. We would def stay here again!

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!