Cabin vacation rentals in Berkshire County

4.86 out of 5 average rating, 285 reviews

A rustic cabin is nestled in a wooded area, featuring a bright red front door and a spacious deck. Surrounding the deck, lush greenery provides a natural backdrop, and a cozy seating area is visible on the porch. A fire pit with stones is situated in the foreground.

Cabin in Stephentown

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

4.97 out of 5 average rating, 216 reviews

A charming two-story cabin is set against a backdrop of lush forest. It features a spacious front porch with multiple windows, allowing for abundant natural light. A well-maintained lawn surrounds the cabin, with a gravel pathway leading to a parked vehicle nearby.

Cabin in Savoy

The Camp - 20 Minutes to Berkshire East!

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.

4.91 out of 5 average rating, 128 reviews

A sunlit sunroom showcases large windows offering views of the surrounding forest. A comfortable sofa is complemented by a colorful throw, with a rustic coffee table positioned in front. Vintage lamps provide soft lighting, enhancing the cozy atmosphere of this inviting space.

Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House is surrounded by acres of forest and is close to conservation areas with hiking trails. Minutes to antiquing, Kripalu, Norman Rockwell Museum, The Mount, Tanglewood, Skiing, Shakespeare & Co. You’ll love my place because of the peace, quiet and seclusion. Located up an old dirt country road. Relax by the wood stove (bring wood), in the sun room or explore nearby Spencertown, Chatham or West Stockbridge. Many ski slopes nearby & a small lake! If visiting in winter, 4wd recommended.

4.9 out of 5 average rating, 278 reviews

A rustic cottage is set against a backdrop of rolling hills and distant mountains. Lush green grass surrounds the property, complemented by well-maintained shrubs. Bright sunlight highlights the exterior, while large windows invite natural light into the cozy interior.

Cabin in Clarksburg

Mountain Cottage Spectacular Views

This lovely cottage sits on 90 acres featuring gardens, fruit groves, forest, and the Hoosic River. Spectacular views of Mt Greylock. Truly an idyllic location, the perfect retreat for a lover of the outdoors but also close to cultural offerings. Less than 10 minutes to downtown North Adams and Mass MOCA. Williamstown and the Clark Art Institute are nearby as well. Plenty of long or short hikes, scenic walks and bike rides as well as local restaurants and shops that are easily accessible.

4.87 out of 5 average rating, 215 reviews

The green cottage features a spacious wooden deck at the front, bordered by lush greenery. A fieldstone chimney is visible, rising from the roof, while large windows bring natural light into the inviting space.

Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the sleeping loft. A 9 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) . BBQ grill, outdoor fire pit . Gates of Tanglewood minutes aaway!

5 out of 5 average rating, 12 reviews

The exterior of a charming red cabin is showcased, featuring a pitched roof and decorative woodwork above the entryway. Large windows allow for natural light. A stone pathway leads to the front door, surrounded by well-maintained landscaping with blooming flowers and lush green grass.

Cabin in Stephentown

Stylish Mountain Cabin Close To Jiminy Peak

Escape to our charming cabin, nestled in the heart of the Berkshires! The cabin features warm, wood-paneled interiors, a stone fireplace perfect for cozying up after a day on the slopes, and large windows that let in plenty of natural light. Whether you're here to ski or simply to relax by the fire, our cabin is the perfect home base for your mountain getaway. With convenient access to ski lifts, hiking trails, and charming restaurants, this retreat promises both adventure and tranquility!

4.99 out of 5 average rating, 250 reviews

A red barn-inspired building with a metal roof is set in a green landscape. A wooden ramp leads to the entrance, flanked by large windows showcasing the surroundings. Two small chairs are positioned on a grassy area, inviting relaxation and enjoyment of the scenic views.

Cabin in Canaan

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.

4.89 out of 5 average rating, 164 reviews

A softly lit sleeping area features a spacious white bed with fluffy pillows. A single wooden chair is positioned nearby, and natural light filters through multiple windows, providing views of the surrounding greenery. The room's neutral palette contributes to a serene atmosphere.

Cabin in Cheshire

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

4.95 out of 5 average rating, 278 reviews

The exterior of a spacious wooden house is presented, featuring a metal roof and large windows. A screened porch and outdoor hot tub are visible. A stone fire pit area is noted, surrounded by a grassy yard with trees in the background.

Cabin in Monterey

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate 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.

4.91 out of 5 average rating, 103 reviews

A cottage with a white exterior is set amidst trees with bare branches, indicating a winter landscape. A gravel path leads to the entrance, and a small porch is visible at the front. Snow lightly dusts the roof, enhancing the serene ambiance.

Cabin in Hinsdale

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.

4.81 out of 5 average rating, 318 reviews

The cabin is set within a grassy area bordered by trees, providing a shaded spot. A picnic table is visible, surrounded by lush greenery and wildflowers. The building features a light exterior and is situated in a peaceful, natural setting.

Cabin in Hillsdale

Rustic, peaceful and affordable cabin

This cabin is in a lovely, peaceful setting. Cozy and private, it has enough room for a big family gathering. The cabin has almost 10 acres of privacy (but with next door neighbors in sight) and lots of outdoor space, but is very close to all of the Berkshires attractions. Skiing at Catamount and Butternut, hiking at Bash Bish and Mount Greylock, biking and swimming at Taconic State Park and its rail trail all close by.