Fitness-friendly holiday rentals in Pittsfield

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.

I enjoyed the 2 months' stay. Thank you, David and Victoria.

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

Tim! Our stay was Beyond my expectations! Many many thanks, appreciation and affection. Be well~ Jen, Lucia and Jack

Great location easy walk to the ski resort. Beautifully decorated with a very comfortable king bed. Nice amenities with hot tub and gym.

Great spot in Mt. Snow! The mountain was extremely accessible and the place is even bigger in person than what it seems in the pictures. Loved our stay here and would definitely come back! Robert and Lindsay were very responsive and made our stay easy!

Ronnie’s place was just what we were looking for. A comfortable place for 5 of us to rest and chat while doing other activities in the area. We got to enjoy the hot tub, covered away from the rain, and played board games indoors. We were also able to prepare a steak dinner on the grill and using the fully furnished kitchen. The neighborhood was a little drab, but his space was a pleasant oasis from it. Still fine to walk around during the day. The neighbors above could be heard walking inside, but this was expected and they didn’t bother us on our vacation. Though they did park a little close for us to comfortably fit in our 3 cars into the 4 slots allowed. But street parking was also fine directly in front of the house. Overall, we enjoyed our time spent at his place, and he kept it neat and accommodating. A great value when you want a hot tub, 1.5 baths, a grill, comfortable queen beds, and pull out. I wish the weather was better for us to enjoy more of his furnished patio space.

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.

This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.

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

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.

Dean and Tina are excellent hosts! We had a great weekend on the mountain. Their home is very comfortable and awesome location.

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

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!!!

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

Awesome property for a weekend getaway from the city. Sonny made this place into a fun playground - the pond is amazing, the hot tub, sauna, and back deck felt like a spa, and we enjoyed the fire pit and taking a short hike to the creek. The house itself is simple but has everything you need and we even managed to order Uber eats once from Kingston. The area is great, and we enjoyed the villages and a nice hike in the area. We will definitely come back.

My 11-day stay at Mary's was truly tranquil and restorative. The grounds are exquisitely maintained, full of color and delight. it was lovely to wake each morning see new blooms opening up into the day. The weather couldn't have been more perfect, allowing for outdoor meals & long afternoons reading on the back porch-the only sounds wind in trees, water in nearby streams, birdsong & in the evenings, the trill of peepers by the pond. all with the stunning view of the mountains in the distance. The house itself is beautifully appointed, furniture, beds, bedding and decor, all high quality. The kitchen is totally stocked with first-rate appliances, a joy to cook in. and I can say without any doubt, this is the only airbnb i've stayed in where the artwork and the books were EXCELLENT. Mary is the best kind of host- helpful, thoughtful, and incredibly responsive. Her attention to detail and kind consideration were likewise everywhere evident. I can't wait to return! thank you Mary!

Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.

Absolutely incredible stay — this place deserves every single one of its five stars and then some! From the moment we arrived, check-in was a breeze, setting the tone for a completely stress-free weekend. The home was spotless, spacious, and thoughtfully set up for comfort and fun. We were blown away by the amenities — a hot tub for relaxing, a pool table and ping pong table for friendly competition, and a cozy fire pit perfect for unwinding in the evenings. Every room felt inviting, and the beds were exceptionally comfortable — we all slept like rocks. Whether you're looking to kick back or stay entertained, this home has it all. I would recommend this gem without hesitation — 1000% worth it!

This is the second time I've stayed there, each time with 6 people (our family with 2 kids, plus one set of grandparents). It's very cozy, convenient with a master bedroom and bathroom on the ground floor which is great for the elderly. The sun room is a great place for meals and board games. The workspace in the basement has great wifi and a high-speed internet connection, which I used for video conferencing all week. We will likely be back again!

My boyfriend and our friends escaped the city and took a 2 hr train ride to Hudson. The house was only about a 15min Uber from the the train. We literally had everything we needed and some. We adored the house, felt right at home. We grilled a bit, thankfully the weather was perfect for a nice fire pit chat. The house itself was cozy and inviting, giving us the best sleep. The house nestled away in nature yet just a short drive from a charming town filled with restaurants and shops. Count us in to book again!

This home is perfect for a family gathering in Albany. The bedrooms were spacious and on three different levels, so everyone had privacy when needed. The eat-in kitchen with large table easily sat all 6 of us for shared meals. We loved the location, so close to all the highways yet tucked away in a quiet neighborhood.