Pittsfield Vacation Rentals

Name: Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Address: Monterey

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 Pittsfield

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

$534

includes taxes & fees

$491 per night

Nov 6 - Nov 7

With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.

Pool

Hot Tub

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

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

Hot Tub

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

$512

includes taxes & fees

$512 per night

Nov 6 - Nov 7

Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.

Kitchen

Washer

Secluded Family Home in Serene Stockbridge Woods

Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.

Kitchen

Washer

Spectacular views and close to Great Barrington.

Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.

Pool

Kitchen

Berkshire Village Carriage House - Super Private!!

$220

includes taxes & fees

$197 per night

Nov 11 - Nov 12

Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

Kitchen

Free WiFi

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

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

Hot Tub

Kitchen

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker Meetinghouse.

Kitchen

Washer

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

With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.

Kitchen

Washer

Tranquil 3-BR Waterfront Retreat

Located in Becket, this vacation home is on the waterfront, within a 5-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

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

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

When you stay at this vacation home in Monterey, you'll be on a lake, within a 5-minute drive of Beartown State Forest and Bidwell House Museum.

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.