Berkshire County Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Berkshire County

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA

With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.

Kitchen

Washer

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

Otis MA

When you stay at this vacation home in Otis, you'll be in the mountains, within a 10-minute walk of Lift Line and Slalom.

Hot Tub

Kitchen

19th c. Barn in the Berkshires

Cheshire MA

When you stay at this vacation home in Cheshire, you'll be in the mountains, within a 5-minute drive of St Mary's of the Assumption Church and Cheshire Reservoir.

Kitchen

Washer

Riverside Retreat in the Berkshires

Great Barrington MA

$253 nightly

$282 total

Oct 26 - Oct 27

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic River.

Kitchen

Washer

Enjoy comfortable elegance in this secluded grand home located in town

Lenox MA

Located in Lenox, this vacation home is in a rural location, within a 15-minute walk of Ventfort Hall Mansion and Gilded Age Museum and Lenox Library.

Kitchen

Washer

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield MA

With a stay at this vacation home in Pittsfield, you'll be on the waterfront, just steps from Pontoosuc Lake and a 4-minute drive from Onota Lake.

Kitchen

Washer

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

West Stockbridge MA

With a stay at this vacation home in West Stockbridge, you'll be in the mountains, within a 10-minute drive of Tanglewood Music Center and Ebenezer II Gifts and Antiques.

Kitchen

Washer

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale MA

With a stay at this vacation home in Hinsdale, you'll be steps from Ashmere Lake and a 4-minute drive from Bas Ridge Golf Course.

Air conditioning

Outdoor Space

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington MA

A stay at this vacation home places you in the heart of Great Barrington, within a 10-minute walk of Housatonic River Walk and Housatonic River.

Kitchen

Washer

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis MA

With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 5-minute drive from County Beach.

Kitchen

Washer

stylish Berkshires Retreat

Lee MA

With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Housatonic River.

Kitchen

Washer

Peace and quiet on the lake

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Berkshire County

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.