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

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room

Stephentown NY

Located in Stephentown, this vacation home is in a rural location, a 4-minute drive from Taconic Ridge State Forest and 6 minutes from John Hancock.

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.

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown MA

With a stay at this vacation home in Williamstown, you'll be within a 15-minute drive of Green Mountain National Forest and Williams College Taconic Golf Course.

RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes

Hancock MA

With a stay at this vacation home in Hancock, you'll be steps from Jiminy Peak Mountain Resort and Cricket Triple Ski Lift.

Berkshire Lake access

Hinsdale MA

With a stay at this vacation home in Hinsdale, you'll be on a lake, just steps from Ashmere Lake and a 3-minute drive from Bas Ridge Golf Course.

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.

Incredible Estate: Pool, Pond, Gym, Arcade, Trails & More: Labor Day Now Open!

Old Chatham NY

Located in Old Chatham, this vacation home is on a lake, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.

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

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.

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.

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.

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.

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.