Fitness-friendly vacation rentals in Pittsfield

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Popular amenities for Pittsfield fitness-friendly rentals

Fitness-friendly apartment rentals

Superhost
An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.
Apartment in Hancock
4.86 out of 5 average rating, 29 reviews

Mountainside Condo Ski on/off

ThomasRating, 5 stars1 month ago
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.
Guest favorite
A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.
Apartment in Hancock
5 out of 5 average rating, 10 reviews

Artsy loft near MassMoCA with pool and hot tubs

NicoleRating, 5 stars1 month ago
We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!
Guest favorite
An expansive living area features high, vaulted ceilings and large windows that provide natural light and views of the outdoors. Wooden bookshelves filled with books line the walls, while comfortable seating is arranged around a central coffee table. A dining table accommodates several guests.
Apartment in Lenox
4.86 out of 5 average rating, 7 reviews

1BR @ The Ponds at Foxhollow - Lenox, MA

VeraRating, 5 stars3 months ago
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts
Guest favorite
A cozy living room is depicted, featuring a dark brown sectional couch facing a 55" UHD Smart TV. An electric fireplace adds warmth, while a decorative area rug enhances the space. Light-colored curtains frame a window, and a plant provides a touch of greenery.
Apartment in Watervliet
4.94 out of 5 average rating, 71 reviews

Uptown Watervliet

Diana TRating, 5 stars4 months ago
Ronnie’s Place was perfect for our stay! Highly recommend as a place to stay if in the Capital Region area as it’s locally on the outskirts of Albany. We were in New York to celebrate a Grandchild’s Sweet 16th Birthday” & “Holiday’s” This place was great for our family visit and made it easier on us. Everything was immaculate & clean. One of my favorites was the bathroom/laundry room it was so nicely decorated with items for laundry use but placed it these awesome essentials bottles. I may add something like that to my laundry room LOL. We didn’t get to utilize the other great amenities due to the weather. We differently will come back again soon as we travel to New York frequently.
Superhost
A welcoming living space is presented, featuring a dark stone fireplace as a focal point. Two armchairs with deer motifs complement a plush sofa, while a coffee table sits centrally. Soft light enters through partially open shades, enhancing the cozy atmosphere.
Apartment in Hancock
4.71 out of 5 average rating, 17 reviews

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

HershyRating, 5 stars8 months ago
place is nice. perfect location. just a snow ball away from all attractions
Guest favorite
A comfortable living area is featured, showcasing a grey sofa adorned with yellow accent pillows. A wooden coffee table sits in front, accompanied by a decorative tray and game. Soft lighting is provided by a tall lamp, while a window with blue shades allows filtered light.
Apartment in Hancock
5 out of 5 average rating, 18 reviews

All-Season Condo at Jiminy Peak (Berkshires)

RobynRating, 5 stars2 months ago
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.
Superhost
The living area features a large sectional sofa and a coffee table, set against a backdrop of light beige walls. A wall-mounted television is positioned above a decorative fireplace, while two bright windows allow natural light to fill the space.
Apartment in Albany
4.89 out of 5 average rating, 9 reviews

/Purple Potty Penthouse\ 1928 Pine Hill 4Bed 1Bath

Venkat Chandra EshwarRating, 5 stars8 months ago
Had a great time here. The hosts are very friendly and helpful especially Mr. Joe who even helped me out to carry my heavy luggage to the 2nd floor. The house is exactly like how it was shown in the photos. If you can afford a 3 or 4 star hotel, then I recommend this beautiful home rather than a hotel and you won't regret it. Kudos to the hosts for their effort in keeping the house in pristine condition.

Fitness-friendly condo rentals

Guest favorite
An aerial view of a multi-level green house surrounded by vibrant autumn foliage. The property is set against a backdrop of rolling hills, with pathways leading toward the house. A gravel driveway and landscaped areas enhance the outdoor space.
Condo in Hancock
4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

EladRating, 5 stars1 week ago
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.
Superhost
Condo in New Ashford
5 out of 5 average rating, 5 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

MichelleRating, 5 stars2 months ago
Great stay! Listing as described. My family really enjoyed our stay.
Superhost
A spacious hot tub is surrounded by a wooden gazebo, featuring an open design that allows for natural light. The wooden slatted structure provides a sense of privacy while offering views of the greenery outside.
Condo in Hancock
5 out of 5 average rating, 5 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

MaryRating, 5 stars2 months ago
We had a wonderful stay at Jiminy Peak.. hosts were super quick to respond with any questions. Very easy check in and check out. Will definitely be staying again in the future!
Condo in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars15 months ago
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+
The exterior of the townhome is presented, featuring a wooden façade complemented by a green roof. A stack of firewood is neatly arranged beside the entrance, and a wooden walkway provides access to the front door. Green shrubs and a small tree add natural elements to the scene.
Condo in Dover
5 out of 5 average rating, 4 reviews

Cozy Townhome by Mt Snow with Ski Home Trail

ChloeRating, 5 stars34 months ago
We had a nice long-term stay at Beth and Kyles's condo while renovating our home. The location is great for Mt. Snow activities. They are pretty hands-off hosts which was fine for us, but might be difficult for some. There is a nice stand-up desk for working from home that I utilized frequently. The condo has internet and for the most part it worked well, but it could be a bit spotty during video calls, so I'd recommend having a back-up plan if video calls are part of your time here. We definitely enjoyed being able to utilize the pool and clubhouse that the condos have access to, and overall enjoyed our stay.
A well-equipped kitchen is presented, featuring white cabinetry and a variety of stainless steel appliances, including a refrigerator, oven, and dishwasher. Countertops are adorned with a contemporary gray pattern, while natural light enters through a nearby window, illuminating the organized space.
Condo in Dover
5 out of 5 average rating, 8 reviews

SKI HOME Trail Bears Crossing Mount Snow

AmyRating, 5 stars14 months ago
The condo was perfect for a ski weekend. It was comfortable and minutes from Mt. Snow. The condo was very clean and kitchen was well equipped. Also conveniently located to restaurants in West Dover and Wilmington.
Superhost
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars14 months ago
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!!!
Guest favorite
The exterior of the Country Inn is displayed, featuring a covered entrance supported by columns and a stone base. A two-story structure showcases multiple windows, providing ample natural light. The building is surrounded by a parking area and nestled against a mountainous backdrop.
Condo in Hancock
4.92 out of 5 average rating, 65 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

MeganRating, 5 stars1 week ago
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.

Fitness-friendly house rentals

Superhost
A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.
Home in Hudson
4.82 out of 5 average rating, 211 reviews

Bright, Airy Home in Hudson w/ TONS of Character!

ElenaRating, 5 starstoday
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.
Guest favorite
A bright bedroom features a four-poster bed draped with crisp white bedding. A patterned rug lies beneath the bed. Artwork adorns the walls, complemented by a sleek black lamp and wooden furniture. Natural light streams through a shuttered window, with a radiator adding warmth.
Home in Hudson
4.94 out of 5 average rating, 17 reviews

Stylish 3BR Hudson House with private backyard

JenniferRating, 5 stars3 weeks ago
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!
Top guest favorite
A view of a modern home surrounded by vibrant autumn foliage, seen from a tranquil pond. The lush greenery and colorful leaves frame the property, creating a serene outdoor setting with a small animal by the water's edge.
Home in Ashfield
4.95 out of 5 average rating, 67 reviews

True Shangri-la, Country Retreat

HillaryRating, 5 stars6 months ago
This home is in the midst of beautiful trees and well off the beaten path. My parents accompanied me to visit my daughter at Smith College, and they said they felt “at peace” in this place and would gladly stay there again. My father marveled at the heating/furnace system (he went down to see the huge pellet bag in the basement and wanted to talk with Mary about how it all worked), which is state-of-the-art and makes the large house a constant comfortable temperature. Mary was very responsive and kept us informed, and my parents visited with her when I was in Northampton for a morning. (My father said he could have talked to Mary all day.) For them, the staircase leading up to the bedroom was a bit challenging, and that would be the only downside to our stay. We had everything we needed, and our mantra whenever we were looking for something was “Mary probably thought of that.” Thank you for everything!
Top guest favorite
A clear set of wooden stairs leads up to the entrance of the cottage, adorned with colorful potted flowers. The side of the house features a soft green hue and a welcoming light fixture above the door. A small fenced yard and landscaped area can be seen in the background.
Home in Southwick
5 out of 5 average rating, 22 reviews

Peaceful, Modern Cottage, 20 min to BDL, 2BR/1BA

LynnRating, 5 stars3 months ago
Jessi's place was exactly as described. It was cute and cozy and perfect for what we needed. Jessi responded to any questions quickly and was very clear in any and all instructions. The neighborhood was peaceful and the house was very easy to find. We will definitely be staying again!
Guest favorite
An aerial view of a spacious Hudson farmhouse is presented, surrounded by lush greenery and a manicured lawn. The property features a large patio area with outdoor seating, and the landscaped grounds provide a serene setting. The home showcases a charming roof and ample outdoor space.
Home in Hudson
5 out of 5 average rating, 8 reviews

Stylish farmhouse w/fireplace by downtown & nature

CherylRating, 5 stars1 month ago
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!
Guest favorite
A serene riverside scene features a seated statue surrounded by natural elements. Colorful fallen leaves blanket the ground, and trees provide a lush backdrop. A gentle stream flows nearby, enhancing the peaceful ambiance of the setting.
Home in Sandisfield
4.96 out of 5 average rating, 71 reviews

Lux on the River near Tanglewood w/220v EV charge

JenyaRating, 5 stars1 week ago
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!
Guest favorite
A charming two-story house is surrounded by greenery, featuring a classic red exterior with white trim. A spacious porch runs along the front, while manicured grounds and a wooden fence enhance the property’s inviting appeal. Trees in the background provide a natural backdrop.
Home in Canaan
4.99 out of 5 average rating, 86 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

lisaRating, 5 stars2 months ago
Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!
Superhost
An inviting entryway showcases a wooden staircase with black railings, leading to an open living area. The exposed brick wall features a TV and a fireplace. Dining furniture is arranged in a spacious layout, with natural light illuminating the room through large windows.
Home in Hudson
4.9 out of 5 average rating, 49 reviews

Historic Home - Downtown Hudson

AlexRating, 5 stars3 weeks ago
Great house to stay in when you're visiting Hudson with a small group. Has all the amenities, walking distance to everything, easy check-in and check-out.

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

Destinations to explore