Skip to content

House rentals in Berkshire County

Book unique vacation rentals, houses, and more on Airbnb

Top-rated house rentals in Berkshire County

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

Home in Stockbridge
Bright Stockbridge country home, near everything!
Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.
$150 per night
Home in West Stockbridge
Retreat to Nature with Sunset Views
Surrounded by pristine wilderness and just minutes from anywhere, this picturesque cottage was completely renovated in 2020, while preserving antique post and beam details from 1900. With sweeping views of Harvey Mountain and overlooking a woodland beaver pond, enjoy access to the best of the Berkshires while feeling at home in this serene sanctuary. 8 minutes to downtown West Stockbridge, 20 minutes to downtown Great Barrington, 15 minutes to Tanglewood, 20 minutes to Butternut Ski Resort.
$232 per night
Home in Chester
Riverfront Getaway
Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!
$139 per night

Vacation rentals in Berkshire County

Cottage in Great Barrington
Artist Cottage at the foot of Monument Mountain
$213 per night
Guesthouse in Lenox
The Granary at House on Golden Hill
$96 per night
Cottage in Becket
Stylish Shales Brook Cottage-Cozy up to happiness
$206 per night
Cottage in Great Barrington
Cozy Country Cottage w Fireplace near Ski Mtns!
$155 per night
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
$246 per night
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
$273 per night
Rental unit in Lenox
Main Street Delight - One Bedroom Apartment
$218 per night
Cottage in Great Barrington
Serene Great Barrington Cottage with Fire Pit!
$148 per night
Tiny home in Lee
Enchanted Tiny Tower nestled in the Berkshires
$197 per night
Rental unit in Canaan
Mountain View Getaway
$86 per night
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
$146 per night
Home in Lenox
Berkshire, MA Getaway! 1/2 mile to town!
$193 per night