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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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The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.

Cabin in Wardsboro

4.85 out of 5 average rating, 153 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

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, 103 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 Washington Park

4.98 out of 5 average rating, 259 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

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, 286 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.

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

4.9 out of 5 average rating, 153 reviews

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

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

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

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

4.96 out of 5 average rating, 46 reviews

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.

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, 275 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, 242 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, 140 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.

Top guest favorite

A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.

4.99 out of 5 average rating, 123 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.

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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

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

4.88 out of 5 average rating, 16 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

Apartment in Hancock

4.76 out of 5 average rating, 17 reviews

Artsy loft surrounded by fall foliage with hot tub

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

Top guest favorite

A spacious living and dining area features a large wooden table and a cozy seating arrangement. A flat-screen TV is mounted above a fireplace, and natural light flows through windows, creating a bright environment. Textured rugs add warmth to the hardwood flooring.

Apartment in Hancock

5 out of 5 average rating, 19 reviews

All-Season Condo at Jiminy Peak (Berkshires)

A dining area featuring a dark wood table surrounded by matching chairs. The walls are painted in a soft gray, creating a calm space. In the background, a living area is visible with a plush sofa facing a wall-mounted television.

Apartment in Cohoes

4.86 out of 5 average rating, 28 reviews

Albany Charm Stylish 1BR Apt in Historic Cohoes

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 spacious living area features two patterned sofas and a wooden coffee table, complemented by a textured area rug. A dining table is positioned nearby, with a large window allowing natural light to illuminate the room. Subtle artwork decorates the walls.

4.89 out of 5 average rating, 111 reviews

Seasons Condo @ Mt Snow (Ski-in/out, hike, bike)

A comfortable living area features a natural stone fireplace as a focal point. Dark leather seating and a cozy armchair are arranged around a simple wooden coffee table. Natural light enters through large windows, with soft curtains framing the view of surrounding greenery.

5 out of 5 average rating, 18 reviews

The Trailside Retreat | Ski on&off w/ Fireplace!

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.

4.95 out of 5 average rating, 74 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 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, 129 reviews

Walk to Mt. Snow-Spa-Summer Pool

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

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, 72 reviews

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

Fitness-friendly house rentals

A two-story wooden house is nestled among lush greenery, featuring a balcony that overlooks the surrounding landscape. Vibrant trees, including a reddish-orange flowering tree, add color to the natural setting, creating a serene atmosphere.

Home in Great Barrington

4.89 out of 5 average rating, 84 reviews

Charming, view, large deck, private/walk downtown

Top guest favorite

An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.

Home in Saugerties

4.98 out of 5 average rating, 165 reviews

Spacious Staycation near HITS & the Hudson

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, 69 reviews

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

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, 117 reviews

Boho-Chic Cape Conveniently Located

Home in Sandisfield

4.96 out of 5 average rating, 78 reviews

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

The living area features natural light streaming through large windows, highlighting exposed wooden beams. A glass coffee table sits centrally on a textured rug, surrounded by a cozy couch and accent chairs. A television is positioned against one wall, completing the inviting space.

Home in Stanfordville

4.96 out of 5 average rating, 104 reviews

Modern farmhouse in Hudson Valley

The exterior of the newly remodeled house is presented, featuring a light blue facade. Two distinct sections are visible, with multiple windows allowing natural light. A small front yard is included, bordered by trees, and a mailbox is positioned near the pathway.

Home in Williamstown

4.97 out of 5 average rating, 94 reviews

Quaint Williamstown Home 3 Bed

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

Total rentals
10 properties
Nightly prices starting at
G$20,913 GYD 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