Chesterfield Country Houses

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Featured Country Houses in Chesterfield

Charming Farmhouse - quiet, private & peaceful

Worthington MA

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Stay at this country house in Worthington. Enjoy laundry facilities, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Hiram H. Fox Wildlife Management Area and Fox Den Wildlife Management Area are located nearby.

Gorgeous Timber Frame Home in Ashfield - 4 bedrooms, 3 bathrooms and Sauna

Ashfield MA

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Stay at this country house in Shelburne Falls. Enjoy free WiFi, a sauna, and laundry facilities. Popular attractions Ashfield Lake and Land of Providence are located nearby.

Hill Ross Farmhouse Historic Homestead

Northampton MA

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Stay at this country house in Florence. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Look Memorial Park and Paradise Pond are located nearby.

Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg MA

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Stay at this country house in Williamsburg. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Petticoat Hill and Brewer Brook Wildlife Management Area are located nearby.

Come stay with us at the Parsonage and enjoy our mountains and rivers.

Charlemont MA

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Stay at this country house in Charlemont. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Charlemont Historical Society and Museum and Bissell Covered Bridge are located nearby.

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

Lenox MA

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Stay at this country house in Lenox. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC

Whately MA

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Stay at this country house in South Deerfield. Enjoy a garden, laundry facilities, and housekeeping. Popular attractions Yankee Candle Village and Mount Sugarloaf State Reservation are located nearby.

Farmhouse on Otis Pond

Otis MA

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Stay at this country house in Otis. Enjoy laundry facilities. Popular attractions Pyramid Lake and Jacob's Pillow are located nearby.

Cozy Farmhouse Retreat in the Berkshires - Chocolog Room

Rowe MA

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Stay at this country house in Rowe. Enjoy free breakfast. Popular attractions Kemp-McCarthy Memorial Museum and Rowe Town Library are located nearby.

Breakfast included

Parking available

Rustic 4-bedroom farmhouse in bucolic Hinsdale, MA

Hinsdale MA

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Stay at this country house in Hinsdale. Enjoy a garden, laundry facilities, and in-room fireplaces. Popular attractions Ashmere Lake and Bas Ridge Golf Course are located nearby.

Cozy Farmhouse Retreat - Judy’s Room

Rowe MA

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Stay at this country house in Rowe. Enjoy free breakfast. Popular attractions Kemp-McCarthy Memorial Museum and Rowe Town Library are located nearby.

Gracious, updated, and classic 5-bedroom farmhouse in gorgeous Chesterfield

Chesterfield MA

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Book a stay at this family-friendly country house in Chesterfield. Enjoy free WiFi, private pools, and a garden. Popular attractions Chesterfield Gorge and Chesterfield Gorge Reservation are located nearby.

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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.

Top trending hotels in Chesterfield

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

CA $204

CA $227 total

Jul 26 - Jul 27

includes taxes & fees

9.4/10 Exceptional! (139 reviews)