Fitness-friendly holiday rentals in Berkshire County

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!

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.

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!

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.

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!

Tranquil Lakeside Escape in the Berkshires

Retreat to this spacious 2-bedroom condo at The Ponds at Foxhollow, nestled in the scenic Berkshires of Massachusetts. Perfect for families or small groups, this peaceful escape offers a pond-view deck, a full kitchen, fireplace, and access to resort amenities like indoor/outdoor pools and a fitness center. Explore hiking trails, waterfalls, and cultural gems nearby. Unwind with stunning views, cozy interiors, and a wealth of year-round outdoor recreation right at your doorstep.

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.

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.

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!