The Berkshires Condo Rentals

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Condo Rentals in The Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$126 nightly

$141 total

Jan 4 - Jan 5, 2026

Total with taxes and 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 Coaster.

Pool

Parking included

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.

Pool

Washer

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.

Air conditioning

Laundry

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.

Pool

Hot Tub

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock MA

$301 nightly

$336 total

Jan 5 - Jan 6, 2026

Total with taxes and 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.

Pool

Kitchen

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

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.

Pool

Hot Tub

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

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.

Pool

Hot Tub

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock MA

$319 nightly

$356 total

Dec 23 - Dec 24

Total with taxes and fees

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.

Pool

Kitchen

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock MA

$270 nightly

$302 total

Jan 6 - Jan 7, 2026

Total with taxes and 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.

Pool

Kitchen

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

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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.