Cabin vacation rentals in Great Barrington

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Top-rated cabin rentals in Great Barrington

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Guest favorite

Cabin in Catskill

4.95 out of 5 average rating, 150 reviews

Restorative Escape in the Woods with Sauna

Escape the city to this private cabin in the woods. Within a 30-minute drive, access skiing at Hunter Mountain, Windham Mountain, or numerous popular hiking trails in Catskill State Park. We are a short drive to scenic towns in the Catskills and Hudson Valley for shopping, restaurants, bars, antiquing, bookstores, vineyards, breweries, farm stands, and local markets. Or stay in and just relax on the property with all the amenities we offer. Perfect for a couples getaway or solo time to unwind.

May 14 – 21

G$35,332 GYD per night

Guest favorite

Cabin in Savoy

4.98 out of 5 average rating, 186 reviews

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.

Oct 9 – 16

G$23,805 GYD per night

Guest favorite

Cabin in Ghent

4.99 out of 5 average rating, 183 reviews

Cozy chalet w/ fireplace near Hudson & hiking

3-bedroom, 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features 5-beds, open floor plan, luxury bathrooms, all-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, NY.

Sep 5 – 12

G$72,828 GYD per night

Guest favorite

Cabin in Copake Lake

4.95 out of 5 average rating, 177 reviews

Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

Festive season is here! And so is the opportunity to stay at an idyllic, secluded property near SKIING, the lake, and hiking! Welcome to the Cabin on Hillside, a peaceful retreat from the hustle and stresses of daily life. Situated in the charming lake town of Copake, you get all the fun of a quaint lakeside community, with the privacy of your own log cabin. After a day of fun, relax in your very own hot tub, swing in the hammock, or cozy up on the couch with some lemonade. Your oasis awaits!

Sep 21 – 28

G$37,828 GYD per night

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 145 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Aug 24 – 31

G$30,576 GYD per night

Guest favorite

Cabin in Cummington

4.98 out of 5 average rating, 162 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Sep 17 – 24

G$14,035 GYD per night

Guest favorite

Cabin in Stockbridge

4.88 out of 5 average rating, 189 reviews

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 cozy sleeping loft. A 8-10 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) Outdoor shower. BBQ grill, great outdoor space to play.

Jan 18 – 25

G$95,744 GYD per night

Guest favorite

Cabin in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

Aug 21 – 28

G$25,681 GYD per night

Guest favorite

Cabin in Canaan

4.99 out of 5 average rating, 231 reviews

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.

Oct 2 – 9

G$34,779 GYD per night

Guest favorite

Cabin in Monterey

4.95 out of 5 average rating, 250 reviews

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.

Jun 5 – 12

G$71,471 GYD per night

Guest favorite

Cabin in Chatham

4.98 out of 5 average rating, 104 reviews

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

May 14 – 21

G$64,310 GYD per night

Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 479 reviews

Serenity Now - Couples Retreat or Writer's Dream

COUPLES RETREAT or SOLO EXCURSION Perfect setting to swoon your partner or write the novel of your dreams. A romantic destination for Engagements, Honeymoons & Anniversaries. Guilford Vermont - no cleaning fee - Easy drive from Boston & NYC ROMANCE SPECIAL - Guests staying 3 nights or more, receive hard cider, cheese and chocolate ($50.00 value) Ask me about ELOPEMENT & VOW RENEWAL CEREMONIES

Dec 24 – 31

G$37,971 GYD per night