Fitness-friendly holiday rentals in Great Barrington

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!

Cozy chalet w/ fireplace near Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features an open floor plan, luxury bathrooms, new, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. The home is surrounded by nature—trees, trails, streams, and farms—all close by. Hike, bike, kayak, or go to a brewery. Discover the nearby Hudson Valley farms, ski in the Berkshires, or visit the trendy town of Hudson.

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.

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.

Private retreat with hot tub near Hudson & hiking

Tucked away behind a row of pine trees lies our charming, private 2-bedroom home on 1.5 acres of land. Relax at our tranquil getaway while having access to all the wonders of the Hudson Valley. Steps from Warren Street in Hudson, Olana, farmstands, and many local parks. Near 3 ski resorts, Bard College, Redhook, fine dining in Rhinebeck, Omega and much more. Enjoy the Catskill Mountains and majestic sunsets on the porch or swings. Stay with us and unwind in the hot tub or yoga room.

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.

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

Sun Soaked Retreat- Short Drive to Warren Street

Bright and spacious, this home is a peaceful escape just a short 10 minute drive to Warren Street’s shops and restaurants. Relax on the sun-soaked deck with your morning coffee or enjoy a cozy movie night in the private screening room downstairs. Nearby, explore scenic hiking trails and local wineries for a taste of Hudson’s charm. Whether you’re here to shop, dine, or unwind, this airy retreat is the perfect home base.

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.