Fitness-friendly vacation rentals in Berkshire County

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in Berkshire County

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

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Guest favorite

A modern home with a dark exterior features large windows and a welcoming entrance. The surrounding landscape includes lush greenery and well-maintained plants, complemented by a gravel pathway leading to the front door, set against a backdrop of a clear blue sky.

Home in Great Barrington

4.97 out of 5 average rating, 34 reviews

All Seasons Berkshires Family Retreat with Hot Tub

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

Superhost

A cozy sitting area features two green sofas positioned around a wooden coffee table. A stone fireplace with a brick surround serves as a focal point. Light filters through the windows, and a leopard-print rug enhances the rustic charm of the wooden walls.

Cabin in Great Barrington

4.91 out of 5 average rating, 32 reviews

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Escape to the Berkshires in our newly-restored, cozy-luxe cabin, complete with fireplace, fully-stocked kitchen, high-speed WIFI, comfy linens, heat/AC and tricked-out basement fun room for the kids! Our cabin sits on a secluded 1.5 acres so it feels remote and peaceful, but it's just 3 minutes from Butternut Ski Resort, 1 minute to hiking the Appalachian Trail, and 7 minutes from downtown Great Barrington with its shops, restaurants and theaters. Just 15 more minutes to Stockbridge and Lenox!

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, 76 reviews

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

Relax with the entire family in this beautiful new home built on the Farmington River. Enjoy luxurious, natural open spaces with fireplace, full size kitchen 2 brms, walk out deck and so much to explore Within short distances enjoy entertainment to Tanglewood, Jacobs Pillow, Becket for Arts. Enjoy family friendly outdoor activities such as hiking at the Colebrook Reservoir or Kayaking on the Otis Reservoir. Don't forget about Fall Foliage and snow skiing. We are located for all diversities.

Top guest favorite

A spacious living area features a large sectional sofa adorned with textured cushions and a sleek coffee table. Natural light floods through tall windows, illuminating the open-plan layout, which seamlessly connects to the dining area with a wooden table and high-backed chairs.

Townhouse in Hancock

5 out of 5 average rating, 24 reviews

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

Guest favorite

A cabin is surrounded by lush greenery, highlighted by a spacious wraparound deck. Two wooden benches and a fire pit are arranged in the backyard, inviting relaxation. Soft lighting twinkles from the deck, creating a warm ambiance as evening approaches.

Home in Becket

5 out of 5 average rating, 6 reviews

Cabin Retreat in the Berkshire Woods

Welcome to Hayscent Hollow, where you'll find seclusion and serenity in the Berkshire woods. Featuring 3 bedrooms and 2 bathrooms, this cabin offers a fully equipped kitchen, a spacious living room and an entertainment room with a pool table and home gym. Step outside to the expansive wraparound deck with a BBQ grill and backyard, or relax in the glassed-in porch and absorb the calm of the forest. Whether you're out exploring or staying in, this home offers comfort and convenience for all.

Guest favorite

A spacious living room features a cozy leather sofa and a soft gray area rug, providing a comfortable environment. Natural light floods in through multiple windows, while a gas fireplace adds warmth. A dining area with sleek chairs is visible in the background.

Home in Sheffield

4.91 out of 5 average rating, 34 reviews

Charming Country House with a Hot Tub

Nested in the southern Berkshire County, this private house is perfect for all seasons. It's a 15 minute drive from Great Barrington as well as skiing, swimming lakes, trails and tons of nature. Set on a secluded 2-acre lot, the house offers ample outdoor space with a hot tub that runs all year, a firepit and out door dining area. The house features an open kitchen and dining area, a spacious and well-appointed living room with a gas fireplace, kids play area, a garage with EV charging.

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

4.93 out of 5 average rating, 14 reviews

Artsy loft near MassMoCA with pool and hot tubs

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!

Superhost

A spacious living area showcases a blue sectional sofa with decorative pillows, paired with an orange armchair. A central coffee table holds magazines and snacks, while large windows invite natural light. A brick fireplace and an open steel staircase add character to the room.

Home in Otis

4.77 out of 5 average rating, 52 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

Enjoy the beauty of the Berkshires in our tranquil retreat! The home, with rustic charm and modern touches, features artwork and furnishings from local Berkshires artists. An expansive, secluded yard located within protected forestland provides the ideal combination of privacy & natural outdoor space. Large enough for your entire family, your home away from home has dedicated spaces for everyone: game room, play area, office, home gym, screened porch, backyard seating, and more!

Guest favorite

A hot tub is positioned outdoors on a wooden deck, surrounded by tall trees. Fresh towels are neatly arranged on a small table nearby. The serene lake, framed by lush greenery, is visible in the background, indicating a peaceful outdoor retreat.

Home in Canaan

4.95 out of 5 average rating, 58 reviews

A/C! Hot Tub, Movie Room, & Private Beach Access!

Welcome to your all-season escape in the heart of the Berkshires & Hudson Valley! Stretch out and relax in this cozy, stylish home that feels worlds away—yet is just minutes from everything. Whether you’re here for skiing, concerts at Tanglewood, wine tasting, or farm-fresh markets, you’re perfectly positioned to enjoy it all. ☀️ SUMMER BONUS: Your stay includes exclusive access to Queechy Lake’s private beach—perfect for sunbathing, swimming, and lakeside lounging.

Superhost

The farmhouse features a charming blue exterior with white trim and a large front porch. A prominent chimney rises from the side of the house. Lush green grass surrounds the home, with trees providing a natural backdrop and an American flag visible at the entrance.

Home in West Stockbridge

4.87 out of 5 average rating, 45 reviews

Magical Berkshires Farmhouse on 18 Glorious Acres!

Enchanting private farmhouse on 18 glorious acres in the beautiful Berkshires. A Writer’s Haven!!! 360-degree scenic PRIVACY. YET… just 1/2 mile off the Mass Pike and 15 minutes from Tanglewood, Lenox & Stockbridge! STUNNING sunset views every evening. Scenic views in every direction. Enclosed, cozy front and back porches, a large country kitchen, a pristine oversized clawfoot bathtub, a massive tree-lined lawn, and a fenced-in pen for your dog! WELCOME!

Guest favorite

A charming gray house is depicted in a snowy landscape, with soft light emanating from a front window. The driveway and yard are covered in fallen leaves, while a wooden fence outlines the property, and a dusting of snow adds a serene touch.

Home in Sheffield

4.9 out of 5 average rating, 83 reviews

Cozy Berkshire Home~No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within steps of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to great hiking, skiing, antiquing & more Seasonal Hot Tub is not available until further notice, sorry for the inconvenience.

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, 134 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.