Cabin holiday rentals in Berkshire County

Peaceful Lakeside Cabin

Peaceful Lakeside Cabin, with a king size bed in the upstairs bedroom, propane heat + infrared stove, internet, washer/ dryer, charcoal grill, canoe, SUP and life vests. Dogs are OK if they are flea free and can remain on the first un-carpeted floor and off the furniture please. Activities include swimming, canoeing, fishing, and hiking. Mass MOCA, Tanglewood, Jacob’s Pillow, Shelburne Falls & Northampton are 40 min drives in various directions. Crooked Pond Cabin is a slice of heaven. Enjoy!

The Camp - hiking trails right outside your door

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

Florida Mountain Log Cabin

Best ski condition and located on the snowmobile trail! Enjoy this stylish custom built 3 BR, 1Full Bath log cabin with a full kitchen on top of Florida Mountain. Outdoor oasis (weather permitting): Firepit, string lights, grill, and the lovers' swings! Conveniently located on the Mohawk Trail and 15 min to Berkshire East. Within an hour from Mt. Snow & Jimminy Peak. Great WiFi and cell reception. Close to North Adams, Williamstown & Deerfield River. Nature, art, and outdoor activities nearby.

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

Lakeshore cabin with beach and dock

A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Newly renovated. Large light-filled living room with cathedral ceiling and skylights. Main bedroom on ground floor with bathroom. Enclosed porch and large deck with gas grill. Swimming and kayaking off the dock. Large lawn with lots of trees. Forest trail and waterfall next door. Plenty of parking. 5 minutes to Tanglewood and Kripalu.

Wildlife Retreat in the Forest

Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish glamping cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood & fantastic interior design. Unwind in the reading nook, master bedroom with skylights, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9-minute walk or 2-minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood is just minutes away.

Amazing Berkshire Mountains Cabin

Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Berkshires Lakefront Boho Modern Retreat

Welcome to Watson Pond Lodge in the Berkshires. This beautiful lakefront contemporary home, with architecture that intentionally focuses on the peaceful lake view, has been designed for your comfort and relaxation. Explore the Berkshires year round and see what the area has to offer: from skiing in the winter, to Tanglewood and Jacob’s Pillow in the summer and leaf peeping in the fall. Or just enjoy the tranquility of our lakefront lodge for a rejuvenating weekend away.

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage.

Spring Mountain Retreat + Views, Fire Pit & Tub

Escape to your modern mountain retreat—perfect for spring getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or spring adventures.