Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

Guests agree: these stays 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

G$26,169 GYD per night
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$33,553 GYD per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 131 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Jan 7 – 14

G$32,211 GYD per night

Popular amenities for Berkshire County vacation rentals

Other great vacation rentals in Berkshire County

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

Feb 28 – Mar 7

G$78,446 GYD per night
Guest favorite

Cabin in Cheshire

4.89 out of 5 average rating, 152 reviews

Private Paradise in the Berkshires

Jun 2 – 9

G$29,776 GYD per night
Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

Dec 4 – 11

G$42,071 GYD per night
Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Oct 27 – Nov 3

G$21,678 GYD per night
Guest favorite

Home in Monterey

4.92 out of 5 average rating, 306 reviews

Charming cottage w/ gorgeous views.

Feb 25 – Mar 4

G$35,044 GYD per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 224 reviews

Berkshire Mountain retreat with Urban eco-luxuries

Mar 17 – 24

G$68,292 GYD per night
Guest favorite

Apartment in Sheffield

4.92 out of 5 average rating, 120 reviews

Private Berkshire Barn Apartment

Oct 19 – 26

G$27,728 GYD per night
Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 171 reviews

Modern studio with views of the treetops

Sep 8 – 15

G$37,566 GYD per night
Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 151 reviews

Cozy apartment near Jiminy Peak

Sep 9 – 16

G$17,302 GYD per night
Guest favorite

Home in Monterey

4.93 out of 5 average rating, 114 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

May 10 – 17

G$30,195 GYD per night
Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 122 reviews

Cozy lakeside cottage

Aug 18 – 25

G$100,980 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 22 – Mar 1

G$18,230 GYD per night

Destinations to explore