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

Home in Great Barrington

5.0 out of 5 average rating, 14 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.

Jan 29 – Feb 5

ﺩ.ﺇ1,815 per night

Guest favorite

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.

May 8 – 15

ﺩ.ﺇ2,131 per night

Guest favorite

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!

Dec 29 – Jan 5

ﺩ.ﺇ804 per night

Guest favorite

Home in Sandisfield

4.93 out of 5 average rating, 41 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.

Sep 11 – 18

ﺩ.ﺇ1,096 per night

Guest favorite

Condo 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.

May 28 – Jun 4

ﺩ.ﺇ605 per night

Guest favorite

Home in Sheffield

5.0 out of 5 average rating, 11 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.

Nov 7 – 14

ﺩ.ﺇ1,868 per night

Guest favorite

Vacation 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.

Nov 21 – 28

ﺩ.ﺇ567 per night

Guest favorite

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.

Dec 4 – 11

ﺩ.ﺇ1,813 per night

Guest favorite

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!

Nov 15 – 22

ﺩ.ﺇ1,956 per night

Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 117 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 & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

Sep 23 – 30

ﺩ.ﺇ4,088 per night

Guest favorite

Apartment in Williamstown

5.0 out of 5 average rating, 69 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.

Jan 8 – 15

ﺩ.ﺇ811 per night

Guest favorite

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.

May 8 – 15

ﺩ.ﺇ3,017 per night