The Berkshires, MA Country Houses from $1,078

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Our top choices for The Berkshires 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

$1,018 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires

A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

Top reviews in The Berkshires

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

Prospect Berkshires

Egremont

10/10 Excellent

Emily

A modern living room with a fireplace, large windows, and a cozy seating area.

Inn At Mount Snow

West Dover

10/10 Excellent

Peter

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

Anonymous traveler

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

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A kitchen with a stainless steel sink, a window with a view of a wooden deck and yellow chairs, and a door leading to an outdoor area.

The Nest Hudson

Hudson

10/10 Excellent

The Nest Hotel is a lovely place that is well situated within walking distance to shops, restaurants, and the river. The room was very comfortable and well appointed and they had a small, but well stocked kitchen with coffee, espresso, and small snacks. Hudson is a beautiful area and perfect for a fall weekend. My sister and I appreciated the hotel's recommendations and the self check-in/check-out instructions were easy to follow. The only downside was that the house next door was under...

Felicia