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Fitness-friendly holiday rentals in Berkshire County

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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 favourite
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
4.98 out of 5 average rating, 43 reviews

Berkshires Family Oasis with Hot Tub, Patio, Gym

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.

Guest favourite
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
4.94 out of 5 average rating, 81 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 favourite
The exterior of a townhome is shown covered in fresh snow, with a covered porch and white railing. Flanked by evergreen trees, the structure features a gabled roof and a single round window above the front entrance, adding character to the picturesque winter scene.
Townhouse in Hancock
5 out of 5 average rating, 31 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 favourite
A spacious living area features a light-colored sofa and an accent chair, with a coffee table centered on a patterned rug. Shelves display decorative items, while a television is mounted above a stone fireplace. Natural light enters through windows accented with blue curtains.
Condo in Hancock
4.92 out of 5 average rating, 13 reviews

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, and be at Jiminy Peak - This condo is for you - right in the heart of Country Village. This Stylish 2BR country Condo w AC is fully updated and comes with parking in front and full access to the Country Inn Amenities ( Fitness, pools, hottub, Tennis etc). This large 900 sq ft condo features country decor, & sleeps up to 7 with a queen, two bunk beds, pull out Trundle, and Full Bed.

Guest favourite
Home in Becket
4.93 out of 5 average rating, 14 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.

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
4.78 out of 5 average rating, 18 reviews

Jiminy Peak Ski Loft 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 favourite
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
4.95 out of 5 average rating, 41 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!

Guest favourite
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, 47 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.

Top Guest favourite
Two glasses of red wine are placed beside a lit candle on a window sill. A plate filled with green grapes and assorted chocolates sits in the foreground. Outside, a vibrant garden of yellow flowers and greenery is visible through the window.
Apartment in Sandisfield
4.95 out of 5 average rating, 56 reviews

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

Guest favourite
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
4.88 out of 5 average rating, 84 reviews

Berkshire Getaway~ 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 favourite
An open living space features exposed wooden beams and a high ceiling, enhancing the rustic charm. Comfortable seating is arranged around a large, round coffee table on a decorative area rug. Large windows provide ample natural light and views of the surrounding landscape.
Barn in Hillsdale
4.97 out of 5 average rating, 164 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Guest favourite
A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.
Home in Pittsfield
4.98 out of 5 average rating, 134 reviews

Hidden Oasis in the Mountains by Evergreen Home

7 MINUTES TO BOUSQUET MOUNTAIN Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Popular amenities for Berkshire County fitness-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Fitness-Friendly apartment accommodation

Top Guest favourite
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, 77 reviews

Peaceful 2 BR apartment minutes from Tanglewood

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
4.82 out of 5 average rating, 38 reviews

Mountainside Condo Ski on/off

Guest favourite
The living room features a cozy sofa and an armchair with a checkered pattern. A large window allows natural light to fill the space, complemented by soft drapery. An entertainment unit with a TV is situated near a decorative mirror and a wooden coffee table.
Apartment in Hancock
5 out of 5 average rating, 7 reviews

Mountain View Jiminy Peak Ski On Off sleeps 4

An outdoor pool is featured at the resort, surrounded by lounge chairs and umbrellas for shade. Views of the well-maintained grounds and pool area are available, with trees and hills in the background. Nearby buildings provide accommodations for guests.
Apartment in Lee
4.92 out of 5 average rating, 25 reviews

Dream Vacation

Superhost
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 serene view of the resort features multiple two-story buildings surrounded by lush green grass and tall trees. A small pond reflects the surroundings, with large stone steps leading toward the water, creating a peaceful atmosphere for guests.
Apartment in Lenox

Lovely Condo w/ Resort Amenities

Superhost
A modern kitchen is characterized by red cabinetry and stainless steel appliances, including a gas stove and a dishwasher. A sleek countertop hosts a kettle and a coffee maker, while natural light enters through a nearby window, enhancing the kitchen's functionality.
Apartment in Hancock
4.69 out of 5 average rating, 26 reviews

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Superhost
A cozy living area features a comfortable couch adorned with soft pillows, complemented by a wooden coffee table. An adjacent kitchen area with modern bar stools offers ample space. Natural light flows through the open layout, and a staircase leads to an upper level.
Apartment in Hancock
5 out of 5 average rating, 3 reviews

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Fitness-friendly condo rentals

Top Guest favourite
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, 62 reviews

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

Guest favourite
A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.
Condo in Hancock
4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

Guest favourite
A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.
Condo in Hancock
4.86 out of 5 average rating, 35 reviews

Jiminy Peak Apartment

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.
Condo in Hancock
4.61 out of 5 average rating, 157 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Ski Jiminy Peak - 1BD

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
A cozy living area features a comfortable sofa grouped with an armchair and a coffee table. A large window allows natural light to illuminate the space, while curtains frame the view. A television is positioned nearby, enhancing the room's functionality.
Condo in Hancock
4.77 out of 5 average rating, 13 reviews

Ski-in/Ski-Out on Jiminy Peak

A serene view of well-maintained landscaping surrounding a tranquil pond is presented. The image captures multiple condo buildings set against a clear blue sky with scattered clouds. Lush green grass leads to the water's edge, framed by several mature trees.
Condo in Lenox
4.56 out of 5 average rating, 18 reviews

Tranquil Lakeside Escape in the Berkshires

Fitness-Friendly Holiday House

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
4.88 out of 5 average rating, 86 reviews

Charming, view, large deck, private/walk downtown

Guest favourite
A comfortable living room is highlighted by two light-colored sofas, accented with colorful throw pillows and blankets. A central coffee table offers board games. A fireplace is visible, alongside a television mounted on the wall above a small work area with a chair. Decorative snowshoes are displayed on the wall.
Home in Hancock
4.92 out of 5 average rating, 13 reviews

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

Top Guest favourite
The home's exterior is framed by vibrant red foliage, creating a striking entryway. A path made of stone leads to the entrance, while steps adorned with leaves provide access. Surrounding greenery enhances the natural setting, offering a serene and inviting atmosphere.
Home in Richmond
4.95 out of 5 average rating, 19 reviews

"Hemlock Shadow" near Tanglewood on Six Acres

Guest favourite
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
4.85 out of 5 average rating, 54 reviews

Jiminy Peak Peaceful Home in Berkshires

Guest favourite
Home in Sheffield
4.85 out of 5 average rating, 13 reviews

Deck, River Views, Mini Gym, Sleeps 8

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
4.78 out of 5 average rating, 60 reviews

Serene Berkshires Home On 5+ Acres, Rustic & Chic

Guest favourite
The exterior of a cozy mountain cabin is shown, featuring a mix of wooden and siding materials. A grassy front yard is bordered by a wooden fence, and trees are visible in the background. The sky is bright with clouds, creating a welcoming ambiance.
Home in Hancock
5 out of 5 average rating, 35 reviews

Cozy Ski Cabin in Berkshires Resort

Guest favourite
A charming two-story farmhouse surrounded by lush greenery and colorful gardens. A spacious screened-in porch extends from the house, providing a serene view of the landscaped yard. The entryway is framed by mature trees, enhancing the peaceful outdoor setting.
Home in West Stockbridge
4.87 out of 5 average rating, 93 reviews

1850's Berkshire farmhouse

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