Great Barrington vacation rentals

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Top-rated vacation rentals in Great Barrington

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

May 17 – 24

$131 per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 254 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Oct 19 – 26

$86 per night

Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Sep 8 – 15

$195 per night

Guest favorite

Apartment in Sheffield

5.0 out of 5 average rating, 319 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Nov 15 – 22

$144 per night

Guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Feb 22 – Mar 1

$138 per night

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 212 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Feb 4 – 11

$624 per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Sep 24 – Oct 1

$101 per night

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 175 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a brand new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

May 8 – 15

$144 per night

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Mar 27 – Apr 3

$78 per night

Guest favorite

Apartment in Sheffield

4.92 out of 5 average rating, 121 reviews

Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Dec 1 – 8

$128 per night

Guest favorite

Vacation home in Great Barrington

4.94 out of 5 average rating, 134 reviews

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family, before you walk into town for a night out! 10 minutes (2 miles) to Butternut Ski Area This brand new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple.

Nov 8 – 15

$188 per night

Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 125 reviews

Newly built cottage on working farm

This light-filled, spacious, newly built, one bedroom cottage sits atop a knoll with full view of a working vegetable farm. Located on a quiet road, you will enjoy a comfortable space adorned with modern features. We are 4 minutes to Catamount ski area, 10 minutes to Great Barrington, and near all the Berkshires has to offer.

Feb 3 – 10

$100 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Great Barrington vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Great Barrington's top sights

Ski Butternut218 locals recommend

Theory Wellness: Recreational and Medical Marijuana Dispensary MA10 locals recommend

Monument Mountain Reservation112 locals recommend

Xicohtencatl Restaurant52 locals recommend

GB Eats32 locals recommend

The Bistro Box47 locals recommend

Other great vacation rentals in Great Barrington

Guest favorite

Home in Egremont

4.93 out of 5 average rating, 256 reviews

Modern Farm House 5 minutes from Great Barrington

Feb 15 – 22

$325 per night

Guest favorite

Home in New Lebanon

4.99 out of 5 average rating, 348 reviews

The old sawmill from 1771

Nov 1 – 8

$125 per night

Guest favorite

Home in Monterey

4.93 out of 5 average rating, 115 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

May 10 – 17

$124 per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 347 reviews

Mid-Century Glass Octagon in the Berkshires

Dec 9 – 16

$327 per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy Berkshires Cottage

Oct 3 – 10

$108 per night

Guest favorite

Apartment in Great Barrington

4.93 out of 5 average rating, 178 reviews

Secluded but not isolated Berkshire Retreat

Jul 9 – 16

$189 per night

Guest favorite

Guest suite in Great Barrington

5.0 out of 5 average rating, 42 reviews

Sweet 1-bedroom with salt water pool

Jun 6 – 13

$113 per night

Guest favorite

Apartment in Great Barrington

4.94 out of 5 average rating, 17 reviews

King Bed | Patio | 2m to Ski Resort

Apr 29 – May 6

$105 per night

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