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Featured Condo Rentals in Cheshire
![UNIQUE - 1BR Country Condo @ Jiminy Peak](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/90b30317_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
UNIQUE - 1BR Country Condo @ Jiminy Peak
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Features include an indoor pool and a gym. Free WiFi and a kitchenette are available in the condo.
Fireplace
Pool
![SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/064023a2_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
The clean condos at this condo building get high marks from our customers. During your stay, 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 a kitchen.
Hot tub
Fireplace
![SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/028b651a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
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 a kitchen.
Hot tub
Fireplace
![Ski-In/Ski-Out at Jiminy Peak in the Country Inn](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/83e307e1_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
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.
![Berkshires Getaway < 1 Mi Skiing & Hiking!](https://images.trvl-media.com/lodging/92000000/91660000/91652800/91652775/9239f0f9_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Berkshires Getaway < 1 Mi Skiing & Hiking!
During your stay at this condo building, you're just a quick walk from Deerfield River. You'll find features such as an arcade/games room. A kitchen and 1.5 bathrooms are available in the condo.
Fireplace
Kitchen
![Mountainside Wyndham Bentley Brook! 2 Bd. dlx.](https://images.trvl-media.com/lodging/97000000/96520000/96514000/96513931/9df84498_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. You'll find features such as an indoor pool, a gym and 1 hot tub. Enjoy your stay with amenities like free WiFi and a kitchen in the condo.
![Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe](https://images.trvl-media.com/lodging/92000000/91730000/91724100/91724063/7a0ff14a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Free WiFi in public areas, an indoor pool and a gym are available. Enjoy your stay with amenities like free WiFi and a kitchen in the condo.
![Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.](https://images.trvl-media.com/lodging/93000000/92630000/92621300/92621238/da84dd3b_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. You'll find features such as an indoor pool, a gym and 1 hot tub. The condo includes amenities such as free WiFi and a kitchen.
![Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.](https://images.trvl-media.com/lodging/93000000/92630000/92621200/92621192/e6cbf72d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Enjoy features like an indoor pool, a gym and 1 hot tub. The condo includes amenities such as free WiFi and a kitchen.
![Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.](https://images.trvl-media.com/lodging/96000000/95930000/95920700/95920694/511b99b9_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Enjoy features like a gym. In-room jetted baths and 2 bathrooms are available in the condo.
![Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe](https://images.trvl-media.com/lodging/71000000/70600000/70593500/70593424/76e68212_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. Enjoy features like an indoor pool, a gym and 1 hot tub. The condo includes amenities such as free WiFi and a kitchen.
![SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/a4425ba9_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
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.
![Ski In & Ski Out - Deluxe 1 Bedroom Condo](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/9c584984_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Ski In & Ski Out - Deluxe 1 Bedroom Condo
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.
![Outside Adventure-Skiing, Hiking, and Relaxation](https://images.trvl-media.com/lodging/101000000/100900000/100899200/100899162/05d25371_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Outside Adventure-Skiing, Hiking, and Relaxation
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. Free WiFi and a kitchen are available 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.
Cheshire Condo Rentals essential information
Accommodation | 46 Condo Rentals |
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Lowest Price | |
Highest Price | |
Popular accommodation | UNIQUE - 1BR Country Condo @ Jiminy Peak, 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, Ski-In/Ski-Out at Jiminy Peak in the Country Inn, Berkshires Getaway < 1 Mi Skiing & Hiking!, Mountainside Wyndham Bentley Brook! 2 Bd. dlx., Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe, Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd., Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx., Cozy couple resort style condo overlooks the beautiful Massachusetts mountains. , Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe, SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, Ski In & Ski Out - Deluxe 1 Bedroom Condo, Outside Adventure-Skiing, Hiking, and Relaxation, Ski on ski off 1 Br loft condo in the village center with private gated parking |
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