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The Berkshires Hotel Guide - Luxury Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Luxury Hotels

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for The Berkshires luxury hotels

A large, two-story house with a well-maintained lawn and a fence.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
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

Devonfield Inn B&B
Lee
€367
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
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

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.
€411
includes taxes & fees
5 Nov - 6 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
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.

3. The Williams Inn

The Williams Inn
Williamstown
€202
includes taxes & fees
8 Nov - 9 Nov
The Williams Inn
A stone building with a wooden staircase and a garden with white flowers.
A room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.
A wooden deck with a railing, a cushioned chair, and a small table with a bottle and glass.
A garden pathway surrounded by various flowering plants and a wooden structure in the background.

4. Troutbeck

Troutbeck
Amenia
€682
includes taxes & fees
1 Nov - 2 Nov
Troutbeck
A modern kitchen with a dining area, a large window, and a view of the garden.
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 kitchen with a dining area, a sofa, and a TV mounted on the wall.
A modern outdoor dining area with a round table and white chairs, surrounded by lush greenery and a white railing.

5. 9 Academy

9 Academy
Salisbury
€559
includes taxes & fees
26 Oct - 27 Oct
9 Academy
A cozy room with a stone wall, a fireplace, and a table with a bottle of champagne in a crystal glass.
A spacious dining area with a high ceiling, stone walls, and a fireplace.
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.

6. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
€364
includes taxes & fees
30 Oct - 31 Oct
The Hermitage Inn Vermont
A large, historic building with a covered porch and outdoor seating area.
A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.
A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.
A sign for the Simsbury House, indicating it is a historic building from 1820.

7. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
€194
includes taxes & fees
19 Nov - 20 Nov
Simsbury 1820 House
A bedroom with a large bed, a chair, and a window with curtains.
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 large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.
A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

8. The White Hart

The White Hart
Salisbury
€305
includes taxes & fees
22 Nov - 23 Nov
The White Hart
An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.
A bar area with wooden beams, a bar counter, and stools.
A spacious bedroom with a large bed, a wooden headboard, a bedside table with a book and a glass, and a window with curtains.
A restaurant with long tables, chairs, and a brick wall.

9. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
€276
includes taxes & fees
15 Nov - 16 Nov
Pocketbook Hotel and Bath
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.
A large, two-story house with a covered porch and multiple chimneys.
A dining room with a brick floor, large windows, and a chandelier.
A cozy living room with a fireplace, comfortable seating, and a view of the outdoors.

10. The Four Chimneys Inn

The Four Chimneys Inn
Bennington
€230
includes taxes & fees
2 Nov - 3 Nov
The Four Chimneys Inn
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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."
Hall 3-night trip
Posted less than an hour ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"clean. local walking distances to everything,"
robert 2-night trip
Posted 4 hours ago
Quality Inn Great Barrington
Hotel On North

Hotel On North

10/10 Excellent
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 2 days ago
Hotel On North
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!"
Richard 1-night trip
Posted 7 days ago
FairBridge Inn Express

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