Berkshire County Vacation Rentals

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Vacation Rentals in Berkshire County

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA

$267 nightly

$298 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a 4-minute walk from Monument Mountain Reservation and within a 5-minute drive of Housatonic River.

Kitchen

Washer

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

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

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

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

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough MA

With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 15-minute drive of Jiminy Peak Mountain Resort and St Mary's of the Assumption Church.

Hot Tub

Kitchen

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee MA

With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Kitchen

Washer

Berkshire House Stay

Lee MA

$989 nightly

$1,105 total

Dec 20 - Dec 21

Total with taxes and fees

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

Kitchen

Washer

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

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Becket MA

$400 nightly

$447 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

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

Kitchen

Pet friendly

A Grand property in Historic Stockbridge

Stockbridge MA

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

Kitchen

Washer

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

Otis MA

Located in Otis, this vacation home is in the mountains, a 2-minute drive from Otis Ridge and 5 minutes from Old Baldy Wildlife Sanctuary.

Hot Tub

Kitchen

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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.