Pittsfield 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

Check dates for Pittsfield hotels

Vacation Rentals in Pittsfield

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA

$267 nightly

$298 total

Dec 7 - Dec 8

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

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont MA

With a stay at this vacation home in Charlemont, you'll be a 4-minute walk from Charlemont Federated Church and 5 minutes by foot from Charlemont Historical Society and Museum.

Washer

Dryer

Berkshire House Stay

Lee MA

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

$337 nightly

$376 total

Dec 8 - Dec 9

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

Don't see what you're looking for?

See all available properties in Pittsfield

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.