The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

The Playhouse is a phenomenal place to host a party! It had EVERYTHING we needed and more. Both the host, Daniel, and the house manager, Ashley, were helpful and responsive. Their documents and information about the house were awesome, and we couldn't have had a better time. Thank you!

Traveled to the Playhouse with four generations of women in my family. The space was gorgeous, comfortable, and accommodating. We were totally content hanging in this beautiful location. The sheets and towels were high quality. The kitchen was fully stocked with all of the appliances and tools we could need to prepare meals. Plenty of parking for all, and there were multiple spaces for everyone to sleep comfortably. We select a different location every year to go to, but seriously considered just coming back here. Would highly recommend.

A huge space and incredibly clean! We had a wonderful time on this beautiful property! The kitchens and outdoor grill were amazing! We loved the fire pit and canoe! The beds were clean and comfortable! I highly recommend this paradise in the Berkshires!

Great place for a big group of friends with kids!

We had a wonderful stay at the Playhouse! The house is absolutely beautiful and quite large -- while still comfortable and easy to make oneself at home. We love to cook and the kitchen was more than fully equipped with everything we needed to create wonderful meals for my mother's 90th birthday family gathering. We did puzzles, had drinks outside, played ping pong, and went for beautiful walks to the lake and the nearby farm. The caretaker and host were both great and extremely responsive. We will definitely be back next year!

The playhouse is one of the best rentals I’ve ever stayed in. The pictures don’t do it justice. It was the perfect place for our large group and the hosts were very accommodating setting up the beds for us and providing lots of great recommendations, etc. Would 100% stay here again.

everything was perfect!

Great house for a family and friends get-together, with tons of space for fun and clean, new bathrooms. Great experience for us.

Responsive host. House is great for large groups. Thuu is a us the second time we stayed here. Kitchen is well appointed. The bed situation limited. The bedroom on first floor really needs a queen bed. All the beds in the large bedroom in lower level are aero beds. Ok for kids but not real beds. Sheets are really cheap and the sofa in the main livining room is very cheap and very uncomfortable. Not really an actually sofa . More like a platform with foam cushions. Overall the place is great but could really stand some upgrades based on the cost to rent it.

Daniel was very caring and understanding the communication was great and the way we had a time at that house was everything!!

The host was very prompt in answering any questions we had. All the beds/linens were very comfortable. Great location - easily accessible to Stockbridge, Great Barrington, and Jiminy Peak.

Beautiful location and beautiful home. House lay-out supported distinct living spaces for multiple family members. Kitchen was incredibly well-stocked, and we loved the Yoga Room!

Our group of 13 women had an absolutely incredible weekend at The Playhouse. The home was spacious, with enough room for us to either all be together comfortably or to spread out and enjoy time doing activities in smaller spaces. The kitchen had everything we could possibly need and more. There were enough bathrooms and sleeping spaces for everyone. We loved that the dining room table was large enough to accommodate everyone for meals and games. We had great communication with both Daniel and Ashely before our arrival and Ashley was available when we had questions during our stay. No one wanted to leave and we are already making plans for coming again.

Excellent stay in the Berkshires. Property was amazing. Home was perfect for 5 couples and 7 kids under the age of six. Loved the history, layout, playroom, and grounds.

Had activities and entertainment for all ages and the kitchen had every item imaginable.

My friends and family stayed at the playhouse for a long weekend together and had a lot of fun. We were a group of 10 adults and 8 children, and there was plenty of space to accommodate everyone. We really liked how open the entire first floor and kitchen were. It made for a lot of fun cooking big meals - and the kitchen was stocked with all supplies needed. And the downstairs made for a great play area for the kids

Such a roomy, beautiful house. Loved the location too. We enjoyed our stay very much! Very clean and everything you could want or need was there.

The Playhouse is absolutely spectacular. The home itself is full of history and honors its roots. This is a unique stay that can host 20 people, which was perfect for our friends trip. We had a great time cooking meals together and exploring the surrounding area. The location is perfect, private but still close to major towns. The hosts were extremely quick and helpful in their responses, provided great guidance/advice, answered all of our questions and addressed all of our concerns. Highly recommend staying here! Thank you Ashley and Daniel!!

We are a group of 7, traveling together for almost 20 years.We have our bucket list of locations!And…yet…We are always looking for the perfect place to stay.The Playhouse checked all our boxes!First the location…Lee , Massachusetts,centrally located in the heart of the Berkshires …yet off the busy main road, steps from a nearby lake, closeby museums, great restaurants, the amazing cultural summer festivals ie.Tanglewood, Jacob’s Pillow, and minutes from the best ever ice cream factory complete with a dairy and their own cows.The house really does have 6 bedrooms and 6 bathrooms and lots of additional space to accommodate sleeper sofas, aero beds, and sleeping bags!Think sleeps 20!!!Two great kitchens, chocked full of amenities, outdoor space with a grill, and three levels ( the first floor has games galore and ping pong, and a room dedicated to yoga, exercise and yet space to find cozy nooks and crannies and settle in with a book!)You have a three person canoe at your disposal.And happily there’s Ashley, the house manager, no problem is too big in her capable hands.Plus she knows what to do and where to go and how to make it happen in an area chocked full of things to see and do!So you can be big:A family reunion, a bachelor party, …or small:a getaway for two, or like us …a group of friends who like to travel , have more friends over, cook, and for two weeks find our happy place, one that’s amazing and works.We all highly recommend The Playhouse!!!

The house and the outside are lovely. The house is big and spacious with lots of beds and bathrooms. The kids congregated in the downstairs playroom and the adults in the main floor, even though the main floor did accommodate all! The facilities are beautiful and the views extraordinary. It is well located, near the High Lawn Farm and the Lake which we used throughout our stay.Overall, it was a super house for our family to be togther!

Fantastic in every way. Thank you!

Had such a wonderful time at the playhouse. Ashley was super helpful. Everyone had a great time from toddlers (room with toys was a nice surprise!) to adults and grandparents. Only downside is there are no king-sized beds - that's clearly shown in booking and doesn't take away from the experience. Would definitely recommend staying here for next big get together.

What a special place to share a weekend with our extended family. Leading up to our stay the property manager, Ashley, reached out to understand how we’d like the sleeping arrangements set up before we arrive. Super accommodating.When we arrived the house was exceptionally clean and set up exactly right. We were also welcomed with fresh flowers and a super thoughtful locally sourced gift basket. The house is beautiful and comfortable and perfect for small children. It really felt made for families while also artfully curated and decorated…a rare mix. Gathering for meals around the large dining table and preparing them in the amazing kitchen with our family was very meaningful and memorable. And easy! The house has everything you could ever dream of needing!Can’t say enough about Ashley and her careful and warm care for us and our experience. So grateful for our time at the Play House.

Everything could not have gone more smoothly, we were surprised with how well the space accommodated all guests, it was very comfortable and everyone had a great time relaxing. Everything from booking to arriving/checking in and departure went off without a hitch. The property manager was great with the preparation of the house to accommodate the group’s specific needs, and always immediately available. The house is in a great location, private but very close to town to enjoy shops, restaurants etc. Would give 6 stars instead of 5 if I could. Thank you to the owner, property manager, cleaning staff and everyone else involved behind the scenes. John

We had a spectacular stay at the Playhouse! There were 15 of us, and there was plenty of space for everyone. The accommodations were sparkling clean and everything in the house was gorgeous. Ashley was very easy to reach and checked in on us to be sure we had everything we needed. We are planning to come back!

It was our 3rd year staying at the Playhouse and it has helped make our family vacations very magical and memorable. It’s a great place for big meals, family fun and entertainment, and super spacious.

We just had a great girls weekend at the playhouse! Due to the snowy weather we spent a lot of time in the house. It worked out perfectly! Lots of space for a large group to spread out. Sleeping arrangements worked out great and were comfortable. Ashely was great at communicating and very helpful. Would highly recommend to anyone!

A group of 13 of us celebrated a bachelor party here - the house was incredible! Beautiful, unique artwork and accents and completely stocked with everything we could need. It was so spacious and had plenty of rooms and nooks for everyone to be comfortable. We were here in the winter and weren't able to enjoy the outdoor spaces, but we absolutely would come back in warmer weather! Hosts were communicative and helpful and there are plenty of activities in the area, from breweries to mountains and restaurants.

This is my 3rd stay at the Play House over the past several years and it's just the best place to return to. As usual, everything was perfectly appointed and Daniel and Ashley were super accommodating and communicative. The group I was with was blown away by the uniqueness of the property. We'll be back again!

Had a great stay with large family at this unique property. Plenty of room for everyone. Great location to explore the Berkshires. Highly recommend.

We really really enjoyed your amazing home! Beautiful, interesting and what an incredible history! Great kitchen we really enjoyed cooking in it Plus the ping-pong and the games were also great. Our eight year-old niece really enjoyed them very much as we did! Multi hour game of Monopoly was fun and not something we’ve done in a long time. Would love to return !

Our stay at this stunning property was truly unforgettable—one of the most beautiful places we’ve ever visited. Daniel and his team were incredibly attentive and easy to reach, always ready to help with even the smallest questions. I couldn’t recommend this place more highly.

House was fantastic - with plenty of space and we really enjoyed the fire pit. Great place to relax after doing the Pan Mass Challenge Unpaved. The kitchen was so nice we skipped going out to dinner an ate there. Ping pong and foos too!

The Playhouse was a beautiful and dramatic space to host some close friends and family for our daughter's wedding. Everyone wants to go back next year for the anniversary!