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

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont MA

Located in Egremont, this vacation home is in a rural location, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Mount Everett State Reservation.

Kitchen

Washer

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA

With a stay at this vacation home, you'll be centrally located in Great Barrington, within a 10-minute drive of Monument Mountain and Housatonic River.

Hot Tub

Kitchen

Home in Great Barrington

Great Barrington MA

$241 nightly

$269 total

Mar 10 - Mar 11

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Great Barrington, just a 3-minute walk from Housatonic River and 10 minutes by foot from Mahaiwe Performing Arts Center.

Kitchen

Washer

Family Ski Getaway in the Berkshires

Great Barrington MA

$284 nightly

$317 total

Mar 5 - Mar 6

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

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.

Hot Tub

Kitchen

Amore Estate - beautiful room with many places to explore and relax in.

Lenox MA

With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.

Pool

Kitchen

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

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA

Located in Great Barrington, this vacation home is within a 5-minute drive of Ski Butternut and Lake Buel.

Kitchen

Washer

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington MA

Located in Great Barrington, this vacation home is in a rural location, within a 5-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Pool

Kitchen

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA

Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.

Hot Tub

Kitchen

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge MA

$582 nightly

$650 total

Mar 9 - Mar 10

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Stockbridge, within a 15-minute drive of Tanglewood Music Center and Housatonic River.

Kitchen

Washer

Quiet Cabin On Over 12 Acres Of Woods!

Becket MA

With a stay at this vacation home in Becket, 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.