Fitness-friendly holiday rentals in Berkshire County

Wonderful place to stay in Lenox! Approximately 10min drive to Tanglewood and downtown. Fully decked out apartment with all the amenities: full kitchen, toiletries stocked in the bathroom, lovely outdoor patio space. Relatively good value for the Berkshires, which of course, skews expensive. Jack and Tania were very responsive by text but respected our space and privacy in-person. Would absolutely stay again!

A great place for a skiing getaway at Jiminy Peek Resort! Ski - in, ski -out, a lovely appointed condo, with access to a hot tub. Frank was most helpful and friendly. I highly recommend his place.

We had a lovely stay. The location can’t be beat. We were able to ski in and out, walk to village area and the restaurant was down the hall. It was so convenient yet even with everything so close- it was so peaceful and quiet. The directions and communications were detailed making it easy to get in and around once there. The bed was extremely comfortable!! The condo itself was immaculate and the view out to the slopes was fantastic. It had everything we needed! Everyone we encountered was so friendly and helpful! Howie was flexible with the checkin- making it much easier for us to get out onto the slopes! He communicated throughout our stay to be sure we were having a great time! Couldn’t ask for a better stay! Thank you! We will definitely be back!

Accommodations were perfect. Very comfortable. Ski on ski off the mountain and close walk to the lodge and restaurants!

My stay was smooth and the condo was nice. I was on a business trip so I didn't have much time in the room besides sleeping which was quiet

We had a great time in this suite for 2 nights during Easter Weekend . This was a surprise gift for my boys .they absolutely loved the decor/gamers & Minecraft .they already asked to go back .host was very responsive and made sure we had everything we needed .we will definitely be back!

I rented this condo for some of my staff who said their stay was great. Four mechanics sharing a condo at a ski resort, they were easy to please.

Second year in a row staying here. And another perfect vacation. Great location, amenities are perfect, clean condo, and the owner is responsive when needed. Can't wait to stay here again.

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

Hamilton is a wonderful host and the area is always beautiful and fun.

Great stay! Listing as described. My family really enjoyed our stay.

We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!

Great stay for skiing at Jiminey Peak! We would definitely stay here again. Clean, spacious, great location and reasonable price!

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Perfect home base for skiing at Jiminy! It was great for me and my kid plus we got to enjoy the hot tub, pool, breakfast at the country store and dinner at bluebird & co. Justine was a great and communicative host - we hope to return soon!

We stayed for a ski weekend and found the house perfect fit for a group 3 kids skiing and snowboarding. There’s plenty of room in the kitchen in the living room all all we came away extremely satisfied.

Beautiful location. The lake, stream, and woods are pretty. The house is well-stocked and was perfect for our large group. The host Sean was very helpful before and during our stay.

Our family of 7 + 2 dogs found this to be the perfect trip to kick off summer. Space feels larger than the photos portray and is open enough for gatherings while allowing privacy for a few of us who worked remotely. The outdoor areas are perfect, complimented with pristine outdoor furniture. Everything is well maintained both inside and out. Everyone enjoyed the pool with enough room for all and being fenced in for our dogs was a welcome bonus! Our family was able to take advantage of the great hiking & biking nearby and enjoy Great Barrington for dinner. The host Steve was appropriately communicative and responsive throughout. If he’ll have us, we look forward to returning. We highly recommend this Airbnb.

We gathered for New Year's with all our kids and a grandchild. The place is very well setup with bedrooms on 3 levels, so wonderful privacy for all. The living space is cozy with lots of comfortable seating. All the holiday decorations were a nice surprise and put us in a festive mood as soon as we got there. The whole house feels lived in and we immediately felt at home. Kitchen has a huge variety of small appliances and an amazing coffee machine. We'll be back!

We had a great stay at Michelle’s place. It was very conveniently located to the base of Jiminy Peak, which made getting to and from the mountain very easy. The house was very well appointed and had everything we needed. We used the fireplace twice and it was super easy. Having access to the facilities at The Country Inn at Jiminy Peak was great as I am injured and can’t ski currently, so instead I went to the gym each day. My family didn’t want to leave and my kids are asking when we can go back!

The home was exactly the way it is in the photos, only better! Everything was clean and spotless. Plenty of kitchen and laundry supplies to use. The home is in a very secluded and in a quiet neighborhood. You will never see another person unless you drive out of the very long driveway and into town. The backyard was scenic and perfect for the fall season. Overlooking the river, especially in the fall is very scenic and was perfect for what we were hoping for. Communication with the Rental property was kind, courteous and professional. The even offered us a late check out as long as they did not rent the property that day. Me and my 5 family members were very comfortable and enjoyed our stay. I highly recommend this property for all seasons. Will definitely return.

Beautiful home, very spacious. Peaceful. Amazing yard for outdoor activities. Plenty of parking. Would definitely come again

This was our second stay at the Queechy Lake house and it did not disappoint! The home is wonderfully maintained, fully equipped and cozy - we appreciated the new additions of the pool and backyard activities. It rained most of the weekend but we utilized Meredith and Jason’s local recommendations and had a blast.