House vacation rentals in Great Barrington

Find and book unique houses on Airbnb

Top-rated house rentals in Great Barrington

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

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

$108 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.

Sep 4 – 11

$221 per night
Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 137 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Jan 6 – 13

$373 per night

Popular amenities for Great Barrington house rentals

House rentals with a hot tub

Guest favorite

Home in Chester

4.96 out of 5 average rating, 307 reviews

Riverfront Getaway

Dec 9 – 16

$159 per night
Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 100 reviews

Hidden Oasis in the Mountains by Evergreen Home

Dec 12 – 19

$419 per night
Guest favorite

Home in Craryville

4.98 out of 5 average rating, 184 reviews

Modern Home in Woods | Hot Tub | 20 mins to Skiing

Dec 1 – 8

$349 per night
Guest favorite

Home in Otis

4.85 out of 5 average rating, 160 reviews

The Meadows House @ Otis Ridge w/ 7-person hot tub

Jul 12 – 19

$242 per night
Superhost

Home in Copake

4.88 out of 5 average rating, 108 reviews

Dreamy Hudson Valley Lakehouse with Hot Tub

Apr 5 – 12

$328 per night
Guest favorite

Home in Catskill

4.95 out of 5 average rating, 132 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Aug 20 – 27

$451 per night
Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Dec 16 – 23

$198 per night
Guest favorite

Home in Craryville

4.93 out of 5 average rating, 218 reviews

The City Farmers Upstate. Farm house with hot tub

Oct 7 – 14

$310 per night
Guest favorite

Home in Hudson

4.95 out of 5 average rating, 246 reviews

Livingston Farmhouse Escape with hot tub and sauna

Apr 3 – 10

$458 per night
Guest favorite

Home in Highland

4.96 out of 5 average rating, 106 reviews

House in Highland: Secluded Retreat

Mar 11 – 18

$262 per night
Superhost

Home in Saugerties

4.93 out of 5 average rating, 333 reviews

Catskills Oasis | Hot Tub, Fire Pit, Fenced Yard

Apr 14 – 21

$296 per night
Guest favorite

Home in Saugerties

5.0 out of 5 average rating, 131 reviews

Upstate Modern Scandinavian Barn in the Catskills

May 15 – 22

$598 per night

House rentals with free parking

Guest favorite

Home in Egremont

4.96 out of 5 average rating, 102 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

Nov 10 – 17

$585 per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country Cottage

Mar 12 – 19

$135 per night
Superhost

Home in Great Barrington

4.9 out of 5 average rating, 111 reviews

Your own private Berkshires retreat

Oct 15 – 22

$303 per night
Guest favorite

Home in Stockbridge

4.95 out of 5 average rating, 103 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Nov 14 – 21

$241 per night
Guest favorite

Home in Great Barrington

4.93 out of 5 average rating, 107 reviews

Former Sunset View Inn

Jan 11 – 18

$455 per night
Guest favorite

Home in Germantown

4.95 out of 5 average rating, 359 reviews

Scandinavian Barn Featured in Airbnb Magazine

May 28 – Jun 4

$333 per night
Guest favorite

Home in Egremont

4.9 out of 5 average rating, 109 reviews

Cozy Berkshire Cape

May 15 – 22

$275 per night
Guest favorite

Home in Chatham

4.9 out of 5 average rating, 143 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

Dec 13 – 20

$102 per night
Guest favorite

Home in Sheffield

4.97 out of 5 average rating, 115 reviews

Gorgeous Sheffield Home

Apr 3 – 10

$574 per night
Guest favorite

Home in Sheffield

4.93 out of 5 average rating, 111 reviews

A Private Peninsula Retreat In The Berkshires!

Mar 3 – 10

$354 per night
Guest favorite

Home in Kingston

4.97 out of 5 average rating, 269 reviews

This New House

Dec 16 – 23

$125 per night
Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 634 reviews

Dutch Touch Woodstock Cottage

Feb 9 – 16

$114 per night

House rentals with a pool

Guest favorite

Home in Ghent

4.87 out of 5 average rating, 264 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Oct 12 – 19

$252 per night
Guest favorite

Home in Sheffield

4.85 out of 5 average rating, 114 reviews

Race Mountain House

May 2 – 9

$483 per night
Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 434 reviews

Mid Century Mod *fireplace walk to rail trail/town

Sep 3 – 10

$870 per night
Guest favorite

Home in Hudson

4.93 out of 5 average rating, 227 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

Oct 20 – 27

$400 per night
Guest favorite

Home in Litchfield

4.93 out of 5 average rating, 162 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Jun 24 – Jul 1

$455 per night
Guest favorite

Home in Staatsburg

4.98 out of 5 average rating, 105 reviews

Hilltop Escape ~ 25 acre private retreat

Mar 19 – 26

$640 per night
Guest favorite

Home in Saugerties

4.96 out of 5 average rating, 150 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

Apr 24 – May 1

$995 per night
Guest favorite

Home in New Paltz

4.93 out of 5 average rating, 121 reviews

Harrison Field Pool BikeRailTrail 2 Town FirePit

Jan 26 – Feb 2

$670 per night
Guest favorite

Home in Cottekill

4.95 out of 5 average rating, 240 reviews

Peace & Privacy - High Falls (hot tub & salt pool)

Nov 23 – 30

$315 per night
Guest favorite

Home in Woodstock

4.92 out of 5 average rating, 153 reviews

Woodstock Home Close to 3 Towns, Hiking and More

Apr 12 – 19

$139 per night
Guest favorite

Home in Woodstock

4.85 out of 5 average rating, 191 reviews

*March Special* Woodstock Retreat Heated Pool

May 23 – 30

$828 per night
Guest favorite

Home in Catskill

4.93 out of 5 average rating, 162 reviews

The Grandview | Catskill, NY

May 5 – 12

$400 per night

Quick stats about house rentals in Great Barrington

Total rentals

150 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

3.8K reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore