Luxury Hotels, The Berkshires Massachusetts | Expedia

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Check availability on The Berkshires Luxury Hotels

Tonight

Oct 22 - Oct 23

Tomorrow

Oct 23 - Oct 24

This weekend

Oct 23 - Oct 25

Next weekend

Our top choices for The Berkshires luxury hotels

A large, two-story house with a well-maintained lawn and a fence.

A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

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

1. Devonfield Inn B&B

Lee

P23,377

P26,112 total

includes taxes & fees

Nov 2 - Nov 3

A two-story house with a brick entrance and a white facade.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

2. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.

P24,196

P29,270 total

includes taxes & fees

Nov 5 - Nov 6

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A spacious living area with a fireplace, wooden beams, and a large window.

A bar area with wooden beams, red chairs, and a long wooden table.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

3. The Williams Inn

Williamstown

P12,870

P14,376 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with a wooden staircase and a garden with white flowers.

A wooden deck with a railing, a cushioned chair, and a small table with a bottle and glass.

A spacious hotel room with a large bed, a sitting area with a sofa and chairs, a dining table, and a kitchen area with cabinets and a coffee machine.

A garden pathway surrounded by various flowering plants and a wooden structure in the background.

4. Troutbeck

Amenia

P40,634

P48,501 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a dining area, a large window, and a view of the garden.

A modern kitchen with a dining area, a sofa, and a TV mounted on the wall.

A modern kitchen with a wooden dining table, chairs, a pendant light, and a black countertop with a coffee maker and a plant.

A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

5. 9 Academy

Salisbury

P34,606

P39,797 total

includes taxes & fees

Oct 26 - Oct 27

A bedroom with a large bed, a chair, and a window with curtains.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

6. The White Hart

Salisbury

P18,892

P21,725 total

includes taxes & fees

Nov 22 - Nov 23

A large, historic building with a covered porch and outdoor seating area.

A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.

A large, historic house with multiple chimneys, a covered porch, and lush greenery.

A sign for the Simsbury House, indicating it is a historic building from 1820.

7. Simsbury 1820 House

Simsbury Center

P11,034

P13,782 total

includes taxes & fees

Nov 19 - Nov 20

A spacious dining area with a high ceiling, stone walls, and a fireplace.

A white pergola with a stone pathway leading to a house.

A white building with a green roof and a stone wall in the foreground.

A bar area with a long counter and multiple stools, a fireplace with a mantel, and a yellow armchair.

8. The Hermitage Inn Vermont

West Dover

P23,519

P25,871 total

includes taxes & fees

Oct 30 - Oct 31

View all properties

Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent

"This is a five star property. Wonderful breakfast. Indoor pool and hot tub. Convenient free parking. Comfortable bedroom with all the amenities. I recommend to anyone visiting the Lenox/Pittsfield area. Good restaurants nearby."

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent

"clean. local walking distances to everything,"

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

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