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.

This was our second time staying here with Nikolay as the host, and we had an amazing time! The pools and activities are so much fun, my kids (age 15 and 11) had a blast even though it rained a few days. They kept busy in the arcade, indoor pools, and movie theater. The staff is super friendly, grounds are clean, the room is roomy with an awesome jacuzzi tub and deck, the outdoor pool is huge with plenty of seating, and the free laundry is much appreciated! The only thing I would recommend is to bring an extra blanket if you like to sleep with lots of blankets, the ones from the resort are kind of thin. BEST PART is the mini golf! This time we brought our own balls and putters (and our own basketball for the court), but you can get them from the staff too. The grocery store is right up the road and there are several great restaurants in town - Highly recommend The Locker Room for great burgers. We definitely will be back, its a great place and wonderful hosts! Definitely a hidden gem of Massachusetts!

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

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!

We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!

Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

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.

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+

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

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!!!

Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.

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 home in a peaceful setting a short drive to Berkshires attractions. The house was cozy and inviting, with so many beautiful touches that made it feel like a real home instead of an Airbnb that was solely designed for income. Despite the size and many nooks and crannies it was impeccably clean. We were there during some chilly rainy days and it was a lovely place to curl up and read or chat, with plenty of room to spread out. One thing to be aware of, the full bath with shower is on the main level, so using it requires toting shower things up and down the stairs each time. Something to be aware of if there's a group member with less mobility. Very doable with assistance, and the shower is a walk-in which was great. I didn't think anyone in my party would mind the train. Little did I know it would turn out to be the highlight of the trip and best part of the stay. Everyone loved it!

An amazing place for nature-loving families! Everything is fully equipped down to the smallest detail. The location is perfect, and the host is lovely and very responsive. We would love to come back!

We came for a few days with three families, to ski nearby. The house was the perfect size for our group - spread out with different spaces for different groups. There was snow on the ground when we arrived (and was still there when we left), but the driveway was plowed before we got there, and again while we were out one day. The beds were SO comfortable. Hot water was not as hot as home, but we weren't there long so some people skipped a shower :) We hope to return in the summer or fall for a few more nights.

What a spacious, luxurious retreat! My family and I completely enjoyed our stay in Prem and Mary’s beautiful home. Plenty of room to spread out and relax, high-end appliances, top-notch bathrooms and comfortable bedding all made for a happy and pampered stay. We loved sitting up late together around the gas fireplace on the enclosed porch and wow what a treat to have a grand piano in the house (haven’t played one in 30 years!). The house is perfectly located between the charming towns of Stockbridge and Great Barrington, with all the area attractions and restaurants, breweries, etc only a short drive away. Prem and Teagan, the house manager, were so friendly and helpful and responded immediately to any questions we had. Delightful stay in every way and we look forward to a return visit!

My friend and I had a lovely two-night stay at Julie's place. The house is the perfect retreat—peaceful, cozy, and beautifully located. We especially enjoyed the evenings by the wood-burning stove and long, leisurely breakfasts on the porch while listening to the river. The beds were incredibly comfortable, with high-quality pillows and bedding—we both slept so well! I would definitely love to come back someday with my husband to enjoy the peace and quiet, as well as everything else the Berkshires has to offer. Thank you, Julie and Arthur, for sharing your wonderful home with us!

A group of nine old college friends met at this lovely location for a weekend reunion. The house is exactly how it is described and incredibly clean and charming. The hosts were very communicative and incredibly accommodating. The kitchen was well stocked and had everything we needed to cook and feel right at home. The dining room is a beautiful space to gather and the whole house is comfortable, clean and inviting. We love that everyone had their own room and the bathrooms were incredibly clean with lots of extra products on hand. The bedrooms were streamlined without a lot of clutter and very comfortable beds. Everyone in our group remarked that they had a great night sleep. The house has a very interesting history and although it is an older home the owners did a fabulous job with updates and still kept all the original charm and character. Although the weather didn't fully cooperate, we were able to take a beautiful hike close by. We hope to get the chance to stay again next year

Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!