Rent Pittsfield Condos
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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$218 per night from 20 Jan to 21 Jan
NZ$218
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock MA
Stay at this ski condo in Hancock. Enjoy laundry facilities, concierge services and ski-in/ski-out access. Popular attractions Jiminy Peak Mountain Resort and ...
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Hancock MA
Stay at this condo in Hancock. Enjoy a fitness centre, laundry facilities and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
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SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock MA
Stay at this ski condo in Hancock. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock MA
The price is NZ$580 per night from 5 Jan to 6 Jan
NZ$580
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this condo in Hancock. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
Tranquil Lakeside Escape in the Berkshires
Lenox MA
Stay at this condo in Lenox. Enjoy free Wi-Fi, a sauna and laundry facilities. Popular attractions The Mount and Wyndhurst Golf & Club are located nearby.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Hancock MA
Stay at this ski condo in Hancock. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Hancock MA
Stay at this ski condo in Hancock. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Hancock MA
Stay at this condo in Hancock. Enjoy a fitness centre, 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 | 46 Condo Rentals |
|---|---|
Lowest Price | NZ$146 |
Highest Price | NZ$580 |
Popular accommodation | Vacation Village in the Berkshires, Club Wyndham Bentley Brook Resort - 2 Bedroom, Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool , SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7, Tranquil Lakeside Escape in the Berkshires, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths |
Top trending hotels in Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is NZ$187 per night from 2 Jan to 3 Jan
NZ$187
2 Jan - 3 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$229 per night from 11 Jan to 12 Jan
NZ$229
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Fully refundable
The price is NZ$146 per night from 22 Jan to 23 Jan
NZ$146
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
The price is NZ$216 per night from 4 Jan to 5 Jan
NZ$216
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead ...
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
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^Subject to availability and chosen travel dates.