Compare Condo Resort Rentals Cheshire
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Featured Condo Resorts in Cheshire
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
$193 nightly
The price is $216 total per night
$216 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with concierge services, securing valuables, and luggage storage. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
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.
Hotel Options in Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (2,174 reviews)
The Williams Inn
101 Spring Street Williamstown MA
$186 nightly
The price is $208 total per night from Dec 22 to Dec 23
$208 total
Dec 22 - Dec 23
Total with taxes and fees
9.6/10 Exceptional! (549 reviews)
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$93 nightly
The price is $104 total per night from Dec 22 to Dec 23
$104 total
Dec 22 - Dec 23
Total with taxes and fees
8/10 Very Good! (988 reviews)
Cheshire Condo Resorts essential information
Accommodation | 2 Condo Resorts |
|---|---|
Lowest Price | $104 |
Highest Price | $216 |
Popular accommodation | Jiminy Peak Mountain Resort, The Ponds at Foxhollow |