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Fitness-friendly vacation rentals in Pittsfield

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in Pittsfield

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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A cozy seating area features two woven chairs adorned with striped cushions. A small table holds a decorative vase with flowers, set against large windows that frame a vibrant backdrop of autumn foliage outside.

4.91 out of 5 average rating, 113 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Top guest favorite

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

5 out of 5 average rating, 102 reviews

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

Top guest favorite

A spacious living area is furnished with a large teal sofa adorned with decorative pillows. A wall-mounted TV is positioned across from the seating area. Two metallic tables and a stylish rug complement the space, while artwork adds a touch of color to the walls.

Townhouse in Albany

4.98 out of 5 average rating, 256 reviews

Modern & Cozy Cntr Square Townhouse Gem from 1854

This amazing Airbnb will give you all the comforts of home! Tastefully decorated with everything you need and then some!! -> Grab-N-Go items (Coffee, Tea, Light Snacks) -> Smart LED Tvs in (2) Livingrooms & (2) Bedrooms -> NordicTrack & Peloton bicycles -> Smart locks with keyless entry -> Fast wireless WiFi -> Queen beds with premium mattresses & pillow covers -> Fully equipped + utensil stocked kitchen + Keurig Coffee -> Full size washer/dryer And much more so come and enjoy your stay!

Top guest favorite

Apartment in Troy

4.99 out of 5 average rating, 239 reviews

Downtown Trojan Horse Airbnb, Parking, Magic Patio

Chef’s kitchen; garage for 2 cars; 4 Queen head/feet adjusting beds; 1 bed massages; 4 person Bluetooth infrared sauna; treadmill; stationery bike; fast internet. Walk to Farmers Mkt, colleges, restaurants, venues. Original art. Bath w/copper tub/hand shower; 2nd bath, w/shower, washer/dryer. Chairlift; heated towels; finest linens; bathrobes; shades/drapes; skylights; luxury toiletries (French Le Labo); Pack and Play, LR sofa & futon for sleeping. Patio requires ok prior to arrival.

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 surrounded by fall foliage with hot tub

This ski-in/ski-out loft at Jiminy Peak offers all of the amenities you could ever possibly ask for! A spacious 1 bedroom loft that sleeps up to 4 (1 Queen Bed, 1 Pullout Couch) is stylish and comfortable. We are the new owners and we are regularly updating the furniture and decor. A full kitchen, full bathroom with tub, ski locker / equipment storage, laundry in unit, dedicated parking spot, access to 2 pools and 2 hot tubs, a sauna, skiing, mountain cart, ropes course, and more!

Top guest favorite

A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.

4.99 out of 5 average rating, 282 reviews

Cozy chalet w/ fireplace near Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, and year-round getaways.

Top guest favorite

A bright living room is highlighted by a grand piano and a modern gas fireplace, both set against a light brick wall. Large windows provide natural light, and wooden flooring adds warmth. A comfortable dark sofa and armchairs are arranged around a glass coffee table.

Home in Great Barrington

4.99 out of 5 average rating, 77 reviews

Stunning luxury home with pool

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

The open living area showcases a modern curved sectional sofa in dark leather, adorned with cream and patterned pillows. A sleek chandelier hangs from the high ceiling, complemented by a wall-mounted TV and a wooden fireplace. Large sliding doors lead to the outdoor patio.

Home in Hancock

4.94 out of 5 average rating, 35 reviews

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

A small workspace is set against a textured wall showcasing exposed brick and plaster. A wooden desk features a task lamp and decorative items, including a plant and flowers. Nearby, an orange accent chair complements the blue upholstered stool.

Apartment in Mechanicville

4.92 out of 5 average rating, 272 reviews

The BoHo Flat” - Elegance & Charm

You are going to love this place!!! It extremely unique and charming!!! 100 Year old school building converted into luxury apartments! The unit you’re viewing is on the MEZZANINE LEVEL, it’s exclusive to you! The unit overlooks the old gymnasium which Has been converted - It’s One of a kind!! A covered roof top terrace, a outdoor patio with fire pit & bbq. Theres a fitness area (Actual registered FALLOUT shelter of the 60’s) to name a few.

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.

4.82 out of 5 average rating, 241 reviews

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

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

Top guest favorite

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage. A central island features a sink and prep space, complemented by a set of kitchen utensils. Natural light enters through a nearby window.

Apartment in Williamstown

5 out of 5 average rating, 135 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

Condo in Hancock

4.9 out of 5 average rating, 71 reviews

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

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

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Popular amenities for Pittsfield fitness-friendly rentals

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

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

Top guest favorite

The entryway features a covered porch with a wooden deck. Two blue chairs adorned with floral cushions are positioned beside the door. A welcome sign is displayed on the wall, and colorful flowers flourish around the steps, enhancing the inviting exterior.

Apartment in Stillwater

5 out of 5 average rating, 27 reviews

Saratoga Getaway 2

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

The exterior of the Snow Tree Condo is depicted, featuring a two-level building nestled among trees. A sign for 'Snow Tree' is visible, along with a gravel parking area accommodating several vehicles. The backdrop showcases a mountainous landscape under a partly cloudy sky.

Apartment in Dover

4.87 out of 5 average rating, 15 reviews

SnowTree Chalet- Walk to lifts!

A cozy living area showcases a combination of comfortable seating, including a sectional sofa with decorative pillows and a patterned armchair. A wooden table complements the space, while a mounted television is visible on the wall. Natural light enters through the window, enhancing the inviting atmosphere.

Apartment in Hancock

4.83 out of 5 average rating, 6 reviews

Cozy Ski Retreat

A cozy living area features a wood-burning fireplace with a flat-screen TV above. A foldout queen murphy bed is neatly tucked against the wall. A sectional sofa, dark wood coffee table, and a patterned area rug complete the inviting space, with large windows offering views of the outdoors.

Apartment in Dover

4.93 out of 5 average rating, 70 reviews

Walk to main lift! The Handle Studio @ Mt. Snow!

Top 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, 81 reviews

Uptown Watervliet

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

4.68 out of 5 average rating, 22 reviews

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Fitness-friendly condo rentals

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

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.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

Top guest favorite

A comfortable living room features a stone fireplace with a wooden mantel and a large flat-screen TV mounted above. A cozy sectional sofa with decorative pillows offers ample seating. A wooden coffee table and an armchair complement the space, with firewood stacked nearby for convenience.

5 out of 5 average rating, 18 reviews

Seasons Lodge | Trailside Condo w/ Fireplace!

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.

4.87 out of 5 average rating, 242 reviews

Mt Snow Ski In/Out at Seasons

Top 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.

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.

5 out of 5 average rating, 62 reviews

Four Seasons Slope-side Getaway at Mount Snow

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.

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.

4.84 out of 5 average rating, 127 reviews

Walk to Mt. Snow-Spa-Summer Pool

Fitness-friendly house rentals

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

4.79 out of 5 average rating, 56 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

Top guest favorite

The exterior of a two-story home is surrounded by vibrant fall foliage. A wooden swing hangs from a tree, and a mix of green and orange leaves blankets the ground. White outdoor chairs are positioned on the lawn, adding to the inviting atmosphere.

5 out of 5 average rating, 63 reviews

Cozy Country Cape House | Close to Hudson

Top 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.

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

Top guest favorite

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.

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.

5 out of 5 average rating, 27 reviews

New! Gemini House 1892 Farmhouse w/ Pool - Hudson

A red two-story house is surrounded by lush greenery and a gentle slope leading to a stone fire pit. A spacious wrap-around porch extends across the front, providing access to the outdoor area under the dappled sunlight filtering through the trees.

Home in Stanfordville

4.96 out of 5 average rating, 103 reviews

Modern farmhouse in Hudson Valley

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

Total rentals
10 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
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi

Destinations to explore