Pittsfield Condo 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

Condo Rentals in Pittsfield

Club Wyndham Bentley Brook Resort - 2 Bedroom

Hancock MA

When you stay at this condo in Hancock, you'll be next to a golf course, just steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.

Pool

Washer

Tranquil Lakeside Escape in the Berkshires

Lenox MA

With a stay at this condo in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and The Mount.

Pool

Kitchen

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock MA

$336 nightly

$375 total

Sep 15 - Sep 16

Total with taxes and fees

With a stay at this condo, you'll be centrally located in Hancock, steps from Jiminy Peak Mountain Resort and Mountain Coaster.

Pool

Kitchen

Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!

Hancock MA

When you stay at this condo in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and Mountain Coaster.

Air conditioning

Laundry

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Hancock MA

With a stay at this condo in Hancock, you'll be steps from Jiminy Peak Mountain Resort and Mountain Coaster.

Pool

Hot Tub

Peaceful 1BR Condo with Pond View

Lenox MA

With a stay at this condo in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and The Mount.

Pool

Kitchen

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

Hancock MA

When you stay at this condo in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and a 1-minute drive from Mountain Coaster.

Pool

Hot Tub

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Hancock MA

With a stay at this condo in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.

Pool

Hot Tub

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

Hancock MA

Book a stay at this ski condo in Hancock. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Pool

Hot Tub

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock MA

$341 nightly

$381 total

Sep 9 - Sep 10

Total with taxes and fees

With a stay at this condo, you'll be centrally located in Hancock, steps from Jiminy Peak Mountain Resort and Mountain Coaster.

Pool

Kitchen

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

Hancock MA

When you stay at this condo in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and Mountain Coaster.

Pool

Kitchen

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

Hancock MA

A stay at this condo places you in the heart of Hancock, steps from Jiminy Peak Mountain Resort and Mountain Coaster.

Pool

Hot Tub

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.