Fitness-friendly holiday rentals in Great Barrington

Berkshires Family Oasis with Hot Tub, Patio, Gym

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.

Serene 3-BR Berkshires Log Cabin

This spacious and comfortable 3- BR log cabin is the perfect refuge to gather with family and friends. Set on a private 60 acre lot in Becket, MA, the lodge is an inviting retreat; secluded and private in the woods, but close to all the Berkshires has to offer. There are 3 bedrooms, 1 of which has an attached full bath while the other 2 have attached half baths. There is another separate full bath on the main floor and additional half bath with infrared sauna lower level. The main floor feature

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

Modern & Cozy Cntr Square Townhouse Gem from 1854

This amazing Airbnb will give you all the comforts of home! Tastefully decorated with everything you need and then some!! -> Grab-N-Go items (Coffee, Tea, Light Snacks) -> Smart LED Tvs in (2) Livingrooms & (2) Bedrooms -> NordicTrack & Peloton bicycles -> Smart locks with keyless entry -> Fast wireless WiFi -> Queen beds with premium mattresses & pillow covers -> Fully equipped + utensil stocked kitchen + Keurig Coffee -> Full size washer/dryer And much more so come and enjoy your stay!

Cozy chalet w/ fireplace near Hudson & skiing

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

Lux on the River near Tanglewood w/220v EV charge

Relax with the family in this beautiful new home on the Farmington River, featuring open living spaces, a fireplace, full kitchen, two bedrooms, and a walk‑out deck to enjoy the sounds of the water. Explore nearby arts at Tanglewood, with musicians such as James Taylor, Bonnie Raitt, ++, Jacobs Pillow, and Becket, hike the Appalachian Trail, kayak on Otis Reservoir, and enjoy fall foliage or winter skiing (close by Butternut Ski Lodge) A perfect year‑round getaway for every traveler

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

Luxe Farmhouse | Fireplace, Porch & Heated Pool

Welcome to Westview Salthouse — a designer 4BR/3.5BA retreat in Ghent, NY, where modern luxury meets classic Upstate charm. Just minutes from Hudson and Chatham, it’s the perfect base for exploring the Hudson Valley. Enjoy a heated saltwater pool (May–Sept), two fireplaces, two living rooms, a chef’s kitchen, screened porch, and premium amenities. Winter brings nearby skiing and cozy nights by the fire — now booking holiday and winter weekends!

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within steps of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to great hiking, skiing, antiquing & more Seasonal Hot Tub is not available until further notice, sorry for the inconvenience.

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.

New gorgeous design-Hottub+Views+Fireplace nr Ski

Luxury 7BR, 4.5BA home with heated pool, hot tub, movie theater, pool table, and whole-house Sonos. Enjoy stunning views of mountains and meadows from the deck or relax by one of two fireplaces. Chef’s kitchen with premium appliances, spa-like baths, and total privacy. High-speed Wi-Fi throughout, dedicated workspace, central AC, and radiant heat floors. Recently built with no expense spared—perfect for unforgettable getaways.