Holiday houses in Great Barrington

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Top-rated holiday rentals in Great Barrington

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Guest favourite

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.

17–24 May

$322 NZD per night

Guest favourite

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!

19–26 Oct

$207 NZD per night

Guest favourite

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.

8–15 Sep

$423 NZD per night

Guest favourite

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.

16–23 Nov

$330 NZD per night

Guest favourite

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!

22 Feb – 1 Mar

$326 NZD per night

Guest favourite

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.

4–11 Feb

$1,454 NZD per night

Guest favourite

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.

24 Sep – 1 Oct

$226 NZD per night

Guest favourite

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.

7–14 Jun

$335 NZD 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.

27 Mar – 3 Apr

$150 NZD per night

Guest favourite

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.

1–8 Dec

$283 NZD per night

Guest favourite

Holiday 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.

8–15 Nov

$428 NZD per night

Guest favourite

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.

3–10 Feb

$222 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Great Barrington holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

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 holiday rentals in Great Barrington

Guest favourite

Home in Egremont

4.93 out of 5 average rating, 256 reviews

Modern Farm House 5 minutes from Great Barrington

15–22 Feb

$715 NZD per night

Guest favourite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

28 Dec – 4 Jan

$243 NZD per night

Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 42 reviews

Sweet 1-bedroom with salt water pool

6–13 Jun

$273 NZD per night

Guest favourite

Guesthouse in Great Barrington

4.97 out of 5 average rating, 90 reviews

Studio in Bucolic Berkshire Setting

6–13 Sep

$259 NZD per night

Guest favourite

Apartment in Great Barrington

4.94 out of 5 average rating, 17 reviews

King Bed | Patio | 2m to Ski Resort

4–11 Feb

$293 NZD per night

Guest favourite

Home in Great Barrington

4.93 out of 5 average rating, 68 reviews

Quiet home on the hill.

29 Sep – 6 Oct

$324 NZD per night

Guest favourite

Barn in Great Barrington

5.0 out of 5 average rating, 46 reviews

Serene Renovated Barn w/ Firepit

20–27 Nov

$420 NZD per night

Guest favourite

Home in Great Barrington

4.97 out of 5 average rating, 38 reviews

Waterfront Modern Lake Mansfield Retreat

5–12 Feb

$1,228 NZD per night

Show all

Quick stats about holiday rentals in Great Barrington

Total rentals	250 properties
Rentals with dedicated workspaces	140 properties have a dedicated workspace
Rentals with a pool	30 properties have a pool
Pet-friendly rentals	120 properties allow pets
Family-friendly rentals	180 properties are a good fit for families
Total number of reviews	8.4K reviews

Holiday houses in Great Barrington

Top-rated holiday rentals in Great Barrington

Loft in Great Barrington

Apartment in Copake Falls

Cottage in Great Barrington

Apartment in Sheffield

Guesthouse in New Marlborough

Home in Great Barrington

Farm stay in Pittsfield

Guesthouse in Stockbridge

Guest suite in Austerlitz

Apartment in Sheffield

Holiday home in Great Barrington

Cottage in Great Barrington

Holiday rentals for every style

Cabins

Houses

Apartments

Popular amenities for Great Barrington holiday rentals

Stay near Great Barrington's top sights

Other great holiday rentals in Great Barrington

Home in Egremont

Guest suite in South Lee

Guest suite in Great Barrington

Guesthouse in Great Barrington

Apartment in Great Barrington

Home in Great Barrington

Barn in Great Barrington

Home in Great Barrington

Quick stats about holiday rentals in Great Barrington

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore