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

An aerial view of a multi-level green house surrounded by vibrant autumn foliage. The property is set against a backdrop of rolling hills, with pathways leading toward the house. A gravel driveway and landscaped areas enhance the outdoor space.

Condo in Hancock

4.95 out of 5 average rating, 58 reviews

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

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

Guest favorite

The backyard features a spacious lawn surrounded by trees, offering a serene view of the green hills. A deck with seating overlooks a play area equipped with a swing set and slide. A hot tub and a fenced patio area are also present, providing additional outdoor space.

Home in Great Barrington

4.97 out of 5 average rating, 32 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.

Guest favorite

Home in Sheffield

4.83 out of 5 average rating, 12 reviews

Big Deck, River Views, Mini Gym, Sleeps 8

*Inquire about discount for stays of 1 week or longer.* Riverside: 4 bedrooms, 2.5 baths: sleeps 8 in beds, dynamic riverfront access + views, high speed internet, 4 Smart TVs, AC throughout, 2 wood-burning fireplaces + fire pit (wood included!), home gym with treadmill, weight bench, stretching area, outdoor seating with grill on the deck overlooking river, kayak, basketball net, fishing poles. NOTE: Only well-experienced kayakers ought attempt the Housatonic! Pets are welcome with pet fee.

Guest favorite

A private deck is furnished with a small table and chairs, surrounded by wooden railings. Sunlight filters through the nearby trees, creating a natural and relaxed atmosphere for outdoor gatherings.

Condo in Hancock

4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Guest favorite

A fire pit with blue glass stones is shown, surrounded by outdoor seating on a wooden deck. A bottle of wine and two glasses, one filled with red wine, are arranged on the table next to the fire pit. Lush greenery borders the area.

Home in Hancock

4.88 out of 5 average rating, 48 reviews

Jiminy Peak Peaceful Home in Berkshires

Peaceful home in Berkshire Mountains located at Jiminy Peak Resort. 7 minute walk to chair lift or restaurants. Ski or hike from resort. Take advantage of the year round heated pool and hot tub or the gym. Two bedroom two full baths, renovated unit with granite kitchen, mountain views. Pergo/ceramic floors. Cathedral ceiling in family room with fan. New bedding. Great area for winter sports or summer/ spring/fall activities such as tennis, alpine slide, playground or nearby lake.

Superhost

The outdoor area features a softly landscaped setting with a mini golf course and tennis court in the foreground. Two spacious pools and a building with multiple units are visible in the background, surrounded by trees and open sky.

Hotel room in Lee

4.67 out of 5 average rating, 3 reviews

Great Place|2 BD|Kitchen| Pool 

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Superhost

The resort features outdoor amenities including a pool surrounded by lounge chairs and lush greenery. A mini-golf area is visible in the foreground, with a basketball court nearby. A spacious building stands in the background, set against a backdrop of rolling hills.

Hotel room in Lee

5 out of 5 average rating, 3 reviews

Beautiful place|2 BD|Kitchen| Pool

Guest favorite

An inviting pool area is shown, featuring a clear blue water surface reflecting the sunlight. Lush green mountains rise in the background, while a well-maintained terrace surrounds the pool. Seating is available nearby, contributing to a relaxing outdoor environment.

Vacation home in Hancock

4.96 out of 5 average rating, 24 reviews

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

Guest favorite

Apartment in Hancock

4.97 out of 5 average rating, 37 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 favorite

Two wooden Adirondack chairs face a small fire pit, surrounded by a serene wooded area. A picnic table is positioned nearby, with a stack of firewood to the side. The Green River flows gently in the background, framed by vibrant greenery.

Apartment in Williamstown

5 out of 5 average rating, 124 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.

Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 125 reviews

Hidden Oasis in the Mountains by Evergreen Home

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.

Superhost

A spacious lounge area features comfortable seating arrangements in earthy tones, complemented by textured stone walls. Soft lighting from table lamps creates a relaxed atmosphere. Large windows allow natural light to flood the space, with a decorative fireplace adding a warm focal point.

Apartment in Hancock

4.86 out of 5 average rating, 29 reviews

Mountainside Condo Ski on/off

Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Just a short walk back to your vacation home to relax before heading to dinner at one of our on site restaurants. Jiminy offers all that you need in a resort experience – lodging, dining, shopping and an array of activities and entertainment.