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

R2,878 ZAR per night

Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.

Apr 24 – May 1

R2,965 ZAR per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 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 5 – 12

R1,592 ZAR 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.

Dec 12 – 19

R4,913 ZAR 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.

Apr 20 – 27

R2,971 ZAR 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!

Jul 11 – 18

R3,053 ZAR per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 277 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 5 – 12

R2,800 ZAR 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.

Mar 5 – 12

R13,702 ZAR 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.

Apr 23 – 30

R2,991 ZAR 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.

Oct 19 – 26

R2,821 ZAR per night

Guest favorite

Vacation home in Great Barrington

4.94 out of 5 average rating, 136 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 18 – 25

R4,376 ZAR per night

Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 126 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.

Mar 3 – 10

R2,207 ZAR 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 Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Sep 30 – Oct 7

R2,384 ZAR per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 181 reviews

Tiny House on 70 Private Acres in Hudson Valley

Aug 6 – 13

R2,932 ZAR per night

Guest favorite

Home in Egremont

4.93 out of 5 average rating, 256 reviews

Modern Farm House 5 minutes from Great Barrington

Feb 19 – 26

R7,164 ZAR per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 347 reviews

Mid-Century Glass Octagon in the Berkshires

Oct 20 – 27

R7,724 ZAR per night

Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 116 reviews

Hudson Valley Hilltop Barn

Aug 31 – Sep 7

R21,456 ZAR per night

Guest favorite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

Oct 8 – 15

R2,400 ZAR per night

Guest favorite

Home in New Lebanon

4.99 out of 5 average rating, 348 reviews

The old sawmill from 1771

Sep 12 – 19

R2,756 ZAR 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

Oct 2 – 9

R2,616 ZAR per night

Show all

Other great vacation rentals in Great Barrington

Guest favorite

Guest suite in Great Barrington

5.0 out of 5 average rating, 43 reviews

Sweet 1-bedroom with salt water pool

Jun 6 – 13

R2,549 ZAR per night

Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 9 reviews

King Bed |Wi-Fi| 2m to Ski Resort

Jan 28 – Feb 4

R2,770 ZAR per night

Guest favorite

Barn in Great Barrington

5.0 out of 5 average rating, 46 reviews

Serene Renovated Barn w/ Firepit

Dec 29 – Jan 5

R4,289 ZAR per night

Guest favorite

Guesthouse in Great Barrington

4.97 out of 5 average rating, 90 reviews

Studio in Bucolic Berkshire Setting

Sep 21 – 28

R2,630 ZAR per night

Guest favorite

Home in Great Barrington

4.93 out of 5 average rating, 68 reviews

Quiet home on the hill.

Oct 25 – Nov 1

R3,254 ZAR per night

Guest favorite

Home in Great Barrington

5.0 out of 5 average rating, 65 reviews

Granite Ledge, Modern home in a unique setting

Sep 26 – Oct 3

R8,647 ZAR per night

Guest favorite

Home in Great Barrington

4.97 out of 5 average rating, 38 reviews

Waterfront Modern Lake Mansfield Retreat

Dec 24 – 31

R13,567 ZAR per night

Guest favorite

Home in Great Barrington

5.0 out of 5 average rating, 9 reviews

Country Castle-Complete privacy-minutes from town

Apr 24 – May 1

R13,902 ZAR per night

Show all

Quick stats about vacation 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

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Great Barrington?
Yes! Work meets play with ease at over 140 vacation rentals in Great Barrington featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Great Barrington?
Four-legged friends are welcome in Great Barrington. Choose from more than 120 vacation rentals for guests traveling with pets.
Are there Great Barrington vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Great Barrington, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in Great Barrington?
Experience the best of Great Barrington with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Great Barrington?
Great Barrington has more than 140 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Great Barrington have a gym?
Absolutely! We offer over 10 house rentals with a gym in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Great Barrington have air conditioning?
Absolutely! We offer over 140 house rentals with air conditioning in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Great Barrington have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Great Barrington have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Great Barrington?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Great Barrington vacation rentals

Top-rated vacation rentals in Great Barrington

Vacation rentals for every style

Houses

Apartments

Cabins

Popular amenities for Great Barrington vacation rentals

Stay near Great Barrington's top sights

Other great vacation rentals in Great Barrington

Home in Lee

Tiny home in Chatham

Home in Egremont

Chalet in Otis

Barn in Hillsdale

Cottage in Hillsdale

Home in New Lebanon

Farm stay in Pittsfield

Other great vacation rentals in Great Barrington

Guest suite in Great Barrington

Apartment in Great Barrington

Barn in Great Barrington

Guesthouse in Great Barrington

Home in Great Barrington

Home in Great Barrington

Home in Great Barrington

Home in Great Barrington

Quick stats about vacation rentals in Great Barrington

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Great Barrington?

Are there pet-friendly vacation rentals in Great Barrington?

Are there Great Barrington vacation rentals on Airbnb with pools?

How much does it cost to stay in apartment rentals in Great Barrington?

Are there family-friendly house rentals in Great Barrington?

Do house rentals in Great Barrington have a gym?

Do house rentals in Great Barrington have air conditioning?

Do apartment rentals in Great Barrington have a bbq area?

Do apartment rentals in Great Barrington have wifi?

What are the most popular amenities for Apartment Rentals in Great Barrington?

Destinations to explore