Top 10 Pittsfield Country Houses CA $652

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Our top choices for Pittsfield country houses

A modern kitchen with white cabinetry, a wooden table, and a large window providing a view of the outdoors.

1. Charming 6 Bdrm Countryside Stay

Great Barrington

CA $1,430 total

includes taxes & fees

Nov 30 - Dec 1

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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

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A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

alan

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

Pete

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Timothy

A spacious hotel lobby with multiple seating areas, large windows, and a television.

Hampton Inn & Suites Berkshires-Lenox

Lenox

10/10 Excellent

Smadar

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise