Rent Pittsfield Condos
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Condo Rentals in Pittsfield

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 12 Nov to 13 Nov
NZ$200
12 Nov - 13 Nov
includes taxes & fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

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

Tranquil Lakeside Escape in the Berkshires
Lenox
Stay at this condo in Lenox. Enjoy free WiFi, a sauna, and laundry facilities. Popular attractions Tanglewood Music Center and The Mount are located nearby.
Save an average of 15% on thousands of hotels when you're signed in

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
The price is NZ$686 per night from 7 Dec to 8 Dec
NZ$686
7 Dec - 8 Dec
includes taxes & fees
Book a stay at this ski condo in Hancock. Enjoy breakfast (surcharge), a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain ...

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

Charming 3-bedroom condo with WiFi in Williamstown, MA
Williamstown
Stay at this condo in Williamstown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Lower Linear Park and Cole Field are located ...

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
The price is NZ$779 per night from 7 Dec to 8 Dec
NZ$779
7 Dec - 8 Dec
includes taxes & fees
Stay at this condo in Hancock. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...

Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Hancock
Book a stay at this ski condo in Hancock. Enjoy free WiFi, a fitness center, and ski-in/ski-out access. Popular attractions Jiminy Peak Mountain Resort and Mountain ...

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Hancock
Stay at this condo in Hancock. Enjoy a fitness center, laundry facilities, and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
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.
Pittsfield Condo Rentals essential information
Accommodation | 64 Condo Rentals |
|---|---|
Lowest Price | NZ$133 |
Highest Price | NZ$779 |
Popular accommodation | Vacation Village in the Berkshires, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, Tranquil Lakeside Escape in the Berkshires, 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, Charming 3-bedroom condo with WiFi in Williamstown, MA, 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7, Ski-In/Ski-Out at Jiminy Peak in the Country Inn, Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool |
Top trending hotels in Pittsfield

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
The price is NZ$203 per night from 10 Nov to 11 Nov
NZ$203
10 Nov - 11 Nov
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

Hotel On North
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$263 per night from 16 Nov to 17 Nov
NZ$263
16 Nov - 17 Nov
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Save an average of 15% on thousands of hotels when you're signed in

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 20 Nov to 21 Nov
NZ$133
20 Nov - 21 Nov
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
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.
More ways to explore Pittsfield
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
