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Featured Condo Rentals in Chatham

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is €109 per night
€109
14 Dec - 15 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Vacation Village in the Berkshires. During your stay, you'll be within walking distance of Jiminy Peak Mountain Resort. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool. This comfortable condo has 360 condos over 2 floors. A fireplace and a patio are available in each condo.
Pool
Parking included

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. You'll find features such as a gym and laundry facilities.
Air conditioning
Laundry

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Features include a gym, breakfast (surcharge) and 1 hot tub. Free WiFi and a kitchen are available in the condo.
Pool
Hot tub

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock MA
The price is €296 per night
€296
11 Dec - 12 Dec
includes taxes & fees
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Enjoy features like a gym and laundry facilities. The condo offers a kitchen and 2 bathrooms.
Pool
Kitchen

Tranquil Lakeside Escape in the Berkshires
Lenox MA
During your stay at this condo building, you'll be within walking distance of The Mount. Enjoy features like laundry facilities. Free WiFi and a kitchen are available in the condo.

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. An outdoor pool, a gym and breakfast (surcharge) are available. Enjoy your stay with amenities like free WiFi and in-room jetted baths in the condo.

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. An outdoor pool, a gym and breakfast (surcharge) are available. The condo offers free WiFi and in-room jetted baths.
Pool
Hot tub

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. You'll find features such as a gym, 1 hot tub and laundry facilities. The condo offers 2 bathrooms and a Smart TV.

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock MA
The price is €475 per night
€475
15 Dec - 16 Dec
includes taxes & fees
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. An indoor pool, a gym and laundry facilities are available. Free WiFi and a kitchen are available in the condo.

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock MA
The price is €266 per night
€266
11 Dec - 12 Dec
includes taxes & fees
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. A gym, breakfast (surcharge) and laundry facilities are available. A kitchen and a fireplace are available in the condo.
Pool
Kitchen

Peaceful 1BR Condo with Pond View
Lenox MA
During your stay at this condo building, you'll be within walking distance of The Mount. Enjoy features like laundry facilities. The condo offers free WiFi and a kitchen.

Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. An outdoor pool, a gym and 1 hot tub are available. The condo includes amenities such as free WiFi and a kitchenette.

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. An outdoor pool, a gym and an arcade/games room are available. The condo offers free WiFi and a kitchen.

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
Pittsfield MA
During your stay at this condo building, you're just a quick walk from Guido's Marketplace. Enjoy features like an indoor pool, a gym and 1 hot tub. The condo includes amenities such as free WiFi and a kitchen.

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock MA
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Features include an indoor pool, a gym and 1 hot tub. Enjoy your stay with amenities like in-room jetted baths and a kitchen in the condo.
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.
Chatham Condo Rentals essential information
Accommodation | 45 Condo Rentals |
|---|---|
Lowest Price | €109 |
Highest Price | €475 |
Popular accommodation | Vacation Village in the Berkshires, 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, UNIQUE - 1BR Country Condo @ Jiminy Peak, 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous, Peaceful 1BR Condo with Pond View, Ski-In/Ski-Out at Jiminy Peak in the Country Inn, Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5, Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025, The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook |
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