
Fitness-friendly vacation rentals in Pittsfield
Find and book unique fitness-friendly rentals on Airbnb
Top-rated fitness-friendly rentals in Pittsfield
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Popular amenities for Pittsfield fitness-friendly rentals
Fitness-friendly apartment rentals

Mountainside Condo Ski on/off
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.

Ski-InSki-Out Loft Lift&MT.Views
great place to ski for a couple of days. It's right at the norm of the lift so amazing if you look for some snow fun.

Ground Floor Apartment on Hudson River
Comfortable space with fun, eclectic furnishings. We stayed in the apartment at Tim’s while visiting area colleges and didn’t get to fully enjoy the gorgeous views from the Inn’s front porch. Would love to come back and catch a sunset over the Hudson!

SnowTree Chalet- Summer monthly discount 50%
Great location easy walk to the ski resort. Beautifully decorated with a very comfortable king bed. Nice amenities with hot tub and gym.

Artsy loft near MassMoCA with pool and hot tubs
We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!

1BR @ The Ponds at Foxhollow - Lenox, MA
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
place is nice. perfect location. just a snow ball away from all attractions

All-Season Condo at Jiminy Peak (Berkshires)
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.
Fitness-friendly condo rentals

Slopes N Seasons | Trailside Condo at Mount Snow
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.

Renovated Condo - 5 min walk to Mount Snow
beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim
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.

Mt Snow Ski In/Out at Seasons
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.

Ski in/out - 2BR Condo - Indoor Pool/Spa
Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.

Condo w/ great amenities 4-seasons! Ski in Ski out
Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!

New - walk to Mt Snow w/ Tub & Gym
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!

Cozy Condo @ Jiminy Peak
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.
Fitness-friendly house rentals

Comfortable Woodstock Getaway
We loved the space! Comfortable, rustic, with such cool and unique character. We only had one night, but wish we had more time to enjoy this home. The hosts went above and beyond to make us feel welcome and at home, offering us flexible check in and out, even left a bottle of wine to enjoy that evening. Highly recommended!

Bright, Airy Home in Hudson w/ TONS of Character!
This spot is a great value for the price point in the Hudson area! While the kitchen wasn't as fully equipped as you might find elsewhere, the basic amenities and both indoor and outdoor spaces certainly can't be beat at this price point. As a host, Shahidul was communicative and responsive ahead of and throughout our stay! I'd give this a 4.5 star review if possible, but don't want to drop the overall rating too much as it really is a great find for the price point.

Band Camp Road
Our family of 5 had a comfortable and enjoyable stay at Stephen's house. We had lots of room to spread out but also great common spaces to be together. Kitchen was well-stocked and location was beautiful.

Mansion on the hill.
Nothing could’ve prepared us for how great this Airbnb was. Hands-down this is the best Airbnb I’ve ever stayed in. Every bedroom and every bathroom were lovely. The kitchen and butlers pantry were outfitted like a professional chef set it up. Don was a perfect host. And when we got about 6 inches of snow people came and cleaned the driveway and shoveled the steps immediately. We went for a walk late at night in the snow and it was like being in a dream. Cannot recommend this Airbnb more.

Stylish 3BR Hudson House with private backyard
Chelsea was an exceptional host—responsive and accommodating throughout our stay. Her home was beautiful, well-maintained, and offered a comfortable experience. We would absolutely choose to stay here again in the future!

7 minute Walk to TRACK & Broadway!
Great location, especially for SARATOGA RACE TRACK. the place was clean and well maintained. They even left a basket of snacks and some sparkling water for us. Very thoughtful.

Stylish farmhouse w/fireplace by downtown & nature
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!

Boho-Chic Cape Conveniently Located
WE WERE A PARTY OF 8 & WE WERE SO COMFORTABLE STAYING IN CRAIG’S HOUSE!! VERY SPACIOUS AND CLEAN. CRAIG WAS ALSO VERY RESPONSIVE AND HAD EVERYTHING WE NEEDED IN THE HOUSE INCLUDING GAMES FOR A GOOD TIME!!! UPSTAIRS GYM WAS ALSO A PLUS!!!
Quick stats about vacation rentals that are fitness-friendly in Pittsfield
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
550 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Mount Snow Ski Resort
- John Boyd Thacher State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Bash Bish Falls State Park
- Otis Ridge
- Naumkeag
- Beartown State Forest
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Huck Finn’s Playland, Albany