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Fitness-friendly vacation rentals in Pittsfield

Find and book unique fitness-friendly rentals on Airbnb

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Vacation rentals for every style

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Popular amenities for Pittsfield fitness-friendly rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Fitness-friendly apartment rentals

Guest favorite
A charming entrance is framed by blooming pink shrubs and lush greenery, standing in front of a dark-colored home. The wooden fence complements the natural setting, with a soft pathway leading to the welcoming door. Sunlight filters through the trees, enhancing the peaceful ambiance.
Apartment in Lenox
5 out of 5 average rating, 76 reviews

Peaceful 2 BR apartment minutes from Tanglewood

Superhost
The winter scene captures a snowy landscape, with a cluster of white buildings visible. Soft lights illuminate the exteriors, contrasting with the serene white snow covering the ground. Surrounding trees add to the tranquil atmosphere, while a path leads through the snow towards the structures.
Apartment in Wilmington

Luxury 2 Bedroom Suite 202B

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
4.81 out of 5 average rating, 37 reviews

Mountainside Condo Ski on/off

Guest favorite
A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.
Apartment in Hancock
4.95 out of 5 average rating, 44 reviews

Ski-InSki-Out Loft Lift&MT.Views

Superhost
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
4.76 out of 5 average rating, 17 reviews

Artsy loft near MassMoCA with pool and hot tubs

Guest favorite
A cozy studio apartment features a vibrant red bedspread complemented by decorative pillows. A comfortable gray sofa is positioned across from a marble coffee table. Decorative wall art, including a saxophone and music notes, adds a creative touch to the light-filled space, alongside dark curtains over the window.
Apartment in Albany
4.94 out of 5 average rating, 33 reviews

Upscale Listing-Heart of Albany

Guest favorite
An outdoor recreational area is illuminated at night, featuring a billiard table under a gazebo. Guests are seated around picnic tables, enjoying their time. Soft lighting enhances the ambiance, while the yard displays green grass and surrounding structures.
Apartment in Watervliet
4.95 out of 5 average rating, 80 reviews

Uptown Watervliet

Superhost
The exterior of the resort is showcased, featuring a three-story building with multiple balconies overlooking a tranquil pond. Lush greenery surrounds the property, and smooth stones are scattered along the water's edge. The scene is complemented by a clear sky in the background.
Apartment in Lee

Great Place - 2BD/Kitchen/Pool

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Fitness-friendly condo rentals

Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.95 out of 5 average rating, 61 reviews

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

Guest favorite
A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.
Condo in Dover
5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

Guest favorite
A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.
Condo in Dover
4.87 out of 5 average rating, 241 reviews

Mt Snow Ski In/Out at Seasons

Guest favorite
A cozy living area features a large sectional sofa and a wooden coffee table, set on a spacious area rug. Natural light filters through a large window, with a stone fireplace and a mounted television providing warmth and entertainment.
Condo in Dover
4.96 out of 5 average rating, 46 reviews

Ski in/out - 2BR Condo - Indoor Pool/Spa

Guest favorite
A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.
Condo in Dover
4.94 out of 5 average rating, 71 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

Top guest favorite
A tranquil lake reflects the vibrant colors of autumn foliage, showcasing a mix of red, orange, and yellow trees. A small island featuring a cluster of trees and shrubs emerges in the foreground, surrounded by calm waters and a gentle green grass shoreline.
Condo in Dover
5 out of 5 average rating, 62 reviews

Four Seasons Slope-side Getaway at Mount Snow

Superhost
A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.
Condo in Lenox
4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

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

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Fitness-friendly house rentals

Top guest favorite
A spacious living area is highlighted by large windows that provide natural light and views of the outside deck. Comfortable seating arrangements feature two sofas with decorative pillows. A modern fireplace with a stone accent wall adds a contemporary touch, while a round coffee table sits centrally.
Home in Hudson
5 out of 5 average rating, 44 reviews

Sun Soaked Retreat- Short Drive to Warren Street

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
4.97 out of 5 average rating, 29 reviews

Stylish 3BR Hudson House with private backyard

Top guest favorite
A serene view of the surrounding mountains is captured during sunset, with soft sunlight illuminating the landscape. A grassy area is visible, framed by trees, and a wooden deck extends into the view, creating a peaceful outdoor space.
Home in Hancock
4.88 out of 5 average rating, 52 reviews

Jiminy Peak Peaceful Home in Berkshires

Top guest favorite
Aerial view of a charming home nestled among vibrant autumn foliage, showcasing rich reds and yellows. Rolling hills and a serene green field extend in the background, while a quiet road meanders through the picturesque landscape.
Home in Whitingham
5 out of 5 average rating, 68 reviews

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Guest favorite
The exterior of the home features a well-maintained brick facade and a welcoming front entrance. A paved pathway leads to the door, flanked by vibrant flowering shrubs and manicured green lawns. Large windows provide natural light to the interior, enhancing the inviting appearance.
Home in Albany
4.95 out of 5 average rating, 113 reviews

Boho-Chic Cape Conveniently Located

Top guest favorite
A modern kitchen features light wood cabinetry and a spacious countertop. Stainless steel appliances, including a gas stove and dishwasher, are present. Natural light enters through multiple small windows, illuminating the space. An adjacent seating area is visible, contributing to an open layout.
Home in Hillsdale
4.97 out of 5 average rating, 35 reviews

Kanga Sunset Retreat

Superhost
The exterior of the farmhouse is presented, featuring a white clapboard façade and a gabled roof. Several large windows allow natural light, while a stone staircase leads to the entrance. A shaded area is furnished with chairs, surrounded by green lawn and trees.
Home in Ghent
4.92 out of 5 average rating, 13 reviews

Farmhouse and Guesthouse w Pool, Pond and Sauna!

Top guest favorite
The scenic outdoor area features a tranquil salt-water pool surrounded by lounge chairs and umbrellas. A stone patio offers space for outdoor dining, with a table and chairs positioned nearby. Lush greenery and blooming flowers enhance the inviting atmosphere.
Home in Hudson
5 out of 5 average rating, 26 reviews

New! Gemini House 1892 Farmhouse w/ Pool - Hudson

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Quick stats about vacation rentals that are fitness-friendly in Pittsfield

  • Total rentals

    10 properties

  • Nightly prices starting at

    R1,762 ZAR before taxes and fees

  • Total number of reviews

    550 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

Destinations to explore