Browse Pittsfield Condos for Rent
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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 AU$190 per night from 19 Jan to 20 Jan
AU$190
19 Jan - 20 Jan 2026
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock MA
With a stay at this condo in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Hancock MA
With a stay at this condo in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 1-minute drive from Mountain Coaster.
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SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock MA
With a stay at this condo, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock MA
The price is AU$510 per night from 5 Jan to 6 Jan
AU$510
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this condo, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
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.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
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.
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.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Hancock MA
With a stay at this condo in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 1-minute drive from Mountain Coaster.
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 | AU$127 |
Highest Price | AU$510 |
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 AU$163 per night from 23 Jan to 24 Jan
AU$163
23 Jan - 24 Jan 2026
includes taxes & fees
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 11 Jan to 12 Jan
AU$199
11 Jan - 12 Jan 2026
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Fully refundable
The price is AU$127 per night from 21 Jan to 22 Jan
AU$127
21 Jan - 22 Jan 2026
includes taxes & fees
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
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Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
The price is AU$190 per night from 4 Jan to 5 Jan
AU$190
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Holiday Inn Express & Suites Pittsfield - Berkshires by IHG in Pittsfield, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's ...
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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