Great Barrington vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Great Barrington

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

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.

Apr 5 – 12

G$33,611 GYD per night
Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

May 8 – 15

G$26,215 GYD per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 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!

Sep 14 – 21

G$22,386 GYD per night

Popular amenities for Great Barrington vacation rentals

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

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Sep 13 – 20

G$32,097 GYD per night
Guest favorite

Home in Egremont

4.93 out of 5 average rating, 254 reviews

Modern Farm House 5 minutes from Great Barrington

Jun 21 – 28

G$96,106 GYD per night
Guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Jul 17 – 24

G$33,456 GYD per night
Guest favorite

Home in New Lebanon

4.99 out of 5 average rating, 347 reviews

The old sawmill from 1771

Jul 24 – 31

G$30,173 GYD per night
Superhost

Apartment in Great Barrington

4.95 out of 5 average rating, 131 reviews

GB Eclectic Victorian

Dec 3 – 10

G$41,227 GYD per night
Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 116 reviews

Hudson Valley Hilltop Barn

Apr 17 – 24

G$199,202 GYD per night
Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

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

Feb 26 – Mar 5

G$18,262 GYD per night
Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

Sep 11 – 18

G$78,584 GYD per night
Guest favorite

Home in Hillsdale

4.93 out of 5 average rating, 207 reviews

Lake House, Copake Lake, NY

Apr 12 – 19

G$32,584 GYD per night
Guest favorite

Home in Egremont

4.97 out of 5 average rating, 112 reviews

A sunny, quiet chalet beautifully decorated.

Dec 20 – 27

G$106,145 GYD per night
Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 137 reviews

Elegant Year-Round Lakeside Retreat with AC

Jan 6 – 13

G$89,753 GYD per night
Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 reviews

Gingerbread House Tower in the Berkshire Hills

May 13 – 20

G$60,005 GYD per night

Other great vacation rentals in Great Barrington

Guest favorite

Guesthouse in Great Barrington

4.97 out of 5 average rating, 90 reviews

Studio in Bucolic Berkshire Setting

May 24 – 31

G$29,098 GYD per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 17 – 24

G$22,150 GYD per night
Guest favorite

Home in Great Barrington

4.97 out of 5 average rating, 38 reviews

Waterfront Modern Lake Mansfield Retreat

Oct 28 – Nov 4

G$125,815 GYD per night
Guest favorite

Home in Great Barrington

4.97 out of 5 average rating, 31 reviews

Sunsets On Blue Hill, Newly Renovated Farmhouse

Nov 6 – 13

G$101,130 GYD per night
Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 10 reviews

King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires

May 4 – 11

G$25,846 GYD per night
Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 92 reviews

Walk Everywhere! | Relax in Easy Elegance!

Oct 13 – 20

G$61,541 GYD per night
Guest favorite

Home in Great Barrington

5.0 out of 5 average rating, 61 reviews

Granite Ledge, Modern home in a unique setting

Jun 1 – 8

G$80,112 GYD per night
Guest favorite

Guesthouse in Great Barrington

5.0 out of 5 average rating, 43 reviews

Sweet Victorian in Housatonic

Sep 3 – 10

G$45,645 GYD per night
Guest favorite

Guesthouse in Sharon

5.0 out of 5 average rating, 58 reviews

Cottage with a Waterfall View

Aug 19 – 26

G$22,798 GYD per night
Guest favorite

Home in Great Barrington

5.0 out of 5 average rating, 60 reviews

Walk to Town! Great Barrington 4-bedroom farmhouse

May 4 – 11

G$76,820 GYD per night
Guest favorite

Home in Great Barrington

5.0 out of 5 average rating, 16 reviews

Newly remodeled home with all the modern amenities

Oct 31 – Nov 7

G$84,261 GYD per night
Guest favorite

Home in Great Barrington

4.97 out of 5 average rating, 33 reviews

Renovated Downtown Great Barrington House

Mar 8 – 15

G$101,672 GYD per night

Quick stats about vacation rentals in Great Barrington

Total rentals

240 properties

Rentals with dedicated workspaces

130 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

170 properties are a good fit for families

Total number of reviews

8.1K reviews

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 130 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 house rentals in Great Barrington?

    Experience the best of Great Barrington with our house rentals, starting at about $20 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 130 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 house rentals in Great Barrington have wifi?

    Absolutely! We offer over 150 house rentals with wifi in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 130 homes with air conditioning, over 90 homes with a bbq area, over 150 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore