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Featured Condo Rentals in Chester

Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox MA
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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.
Pool
Kitchen
Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View

Lenox MA
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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.
Pool
Kitchen
Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Pittsfield MA
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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.
Pool
Hot tub
A cozy rest in tiny home of a nest (downtown Northampton)

A cozy rest in tiny home of a nest (downtown Northampton)

Northampton MA
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During your stay at this condo building, you're just a quick walk from Smith College. Enjoy features like 1 hot tub and laundry facilities. The condo offers a kitchenette and a patio.
Hot tub
Kitchen
Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge

Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge

West Stockbridge MA
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During your stay at this condo building, you're just a quick walk from Stockbridge Bowl. Enjoy features like a gym and laundry facilities. The condo offers free WiFi and a kitchen.
Pool
Kitchen
Charming 2-Bedroom Condo w/Loft, Swimming Pools, Tennis–Lenox, MA Resort Getaway

Charming 2-Bedroom Condo w/Loft, Swimming Pools, Tennis–Lenox, MA Resort Getaway

Lenox MA
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During your stay at this condo building, you'll be within walking distance of The Mount. A gym and laundry facilities are available. Enjoy your stay with amenities like in-room jetted baths and 2 bathrooms in the condo.
Washing machine
Dryer
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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.

Chester Condo Rentals essential information

Accommodation
14 Condo Rentals
Lowest Price
Highest Price
Popular accommodation
Tranquil Lakeside Escape in the Berkshires, Peaceful 1BR Condo with Pond View, Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025, A cozy rest in tiny home of a nest (downtown Northampton), Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge, Charming 2-Bedroom Condo w/Loft, Swimming Pools, Tennis–Lenox, MA Resort Getaway

Areas of Chester

Other Chester Accommodation Types