Fitness-friendly holiday 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 favourite

Home in Great Barrington

5.0 out of 5 average rating, 16 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 favourite

Home in West Stockbridge

5.0 out of 5 average rating, 54 reviews

Heart of the Berkshires - Bright, Cozy, Near Lake

Welcome to the heart of the Berkshires! This newly furnished home is conveniently located between downtown Stockbridge and Lenox. Minutes to Tanglewood, the Stockbridge Bowl, restaurants, shops, art galleries, Canyon Ranch, Berkshire Botanical Gardens, the Norman Rockwell Museum, etc. A short drive to four ski resorts, including Butternut, Catamount, Bousquet, and Jiminy Peak. Enjoy a diverse culture and restaurant scene and everything that the Berkshires has to offer. Fast wi-fi is available.

Guest favourite

Chalet in Monterey

4.97 out of 5 average rating, 73 reviews

Cozy French Country chalet

Perfectly situated, this cozy French Country chalet is minutes to downtown Monterey, Lake Garfield & just 10 minutes to Butternut for skiing. Family friendly, this home is stocked with games, movies & books for a fun-filled trip. If you're looking for a relaxing Berkshires getaway, look no further than this well-cared-for home, stocked with amenities to make your trip comfortable & relaxing! The home also has upgraded Internet with 2 internet satellite dishes, to handle Zoom calls & home work!

Guest favourite

Home in Sandisfield

4.93 out of 5 average rating, 42 reviews

Luxury on the river@Fish Camp/Close to Tanglewood

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.

Guest favourite

Apartment in Hancock

4.83 out of 5 average rating, 131 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 favourite

Apartment in Hancock

4.95 out of 5 average rating, 19 reviews

Upscale 2 bed/2bath Condo at a Mountain Resort!

A beautiful newly renovated two bedroom condo with A/C at Jiminy Peak Mountain Resort. This natural light filled 1130 sq. ft. condo can accommodate up to 4 people with 2 bedrooms. Two full baths, a washer and dryer as well as a full kitchen will make this your home away from home. This convenient location is just a short distance from area lakes, hiking trails, restaurants, shopping and cultural venues. Take advantage of Jiminys' pools when you're not enjoying the Mountain Adventure Park!

Guest favourite

Holiday home in Hancock

5.0 out of 5 average rating, 8 reviews

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

*NEW to AirBnB* 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 favourite

Home in Pittsfield

4.98 out of 5 average rating, 102 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 & sip coffee as you watch the sunrise over the mountains from the screened-in porch. 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.

Guest favourite

Home in Great Barrington

5.0 out of 5 average rating, 52 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!

Guest favourite

Farm stay in Canaan

5.0 out of 5 average rating, 22 reviews

Spacious farmhouse, beach access & private trails

Our sprawling farmhouse was recently renovated into a serene sanctuary for our guests to rest and recharge. Over 4,500 sq ft, our home features a light-filled chef's kitchen, 5 spacious bedrooms and multiple areas for lounging and entertaining. Great for families and groups. Beautiful trails that wind through a private wooded forest. Short drive to Queechy Lake (beach access and ice skating). Close to skiing (Jiminy, Catamount, more). Quiet road and lots of privacy.

Guest favourite

Flat in Williamstown

5.0 out of 5 average rating, 73 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 favourite

Home in Great Barrington

5.0 out of 5 average rating, 9 reviews

Country Castle-Complete privacy-minutes from town

Welcome to the Country Castle! This expansive home, boasting 7000 square feet, sits on 20 private acres less than five minutes (2-miles) from downtown Great Barrington. A 12 minute drive (6-miles) to either Butternut or Catamount for a day on the slopes. Making this home extremely convenient to all Berkshire amenities. Meander from your own backyard directly on to multiple hiking/snowshoeing trails to enjoy for hours.