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Find Luxury Hotels in The Berkshires

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Check availability on The Berkshires Luxury Hotels

Tonight
14 Sept - 15 Sept
Tomorrow
15 Sept - 16 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

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
S$579
includes taxes & fees
15 Sept - 16 Sept
Devonfield Inn B&B
A stone fountain surrounded by trees in a park setting.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
S$578
includes taxes & fees
15 Sept - 16 Sept
The Inn at Stockbridge
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A white two-story house with a front door, windows, and a chimney.

3. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
S$505
includes taxes & fees
15 Sept - 16 Sept
The Old Inn On The Green
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 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.

4. 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.
S$506
includes taxes & fees
28 Sept - 29 Sept
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.
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.

5. The Williams Inn

The Williams Inn
Williamstown
S$267
includes taxes & fees
15 Sept - 16 Sept
The Williams Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A modern apartment with a living room, kitchenette, and dining area.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
  • Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
S$139
includes taxes & fees
5 Oct - 6 Oct
The Central Downtown Inn & Suites
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
A dining room with a large table set for a meal, surrounded by ornate chairs.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
S$310
includes taxes & fees
21 Sept - 22 Sept
Hampton Terrace Inn
A stone building with a wooden staircase and a garden with white flowers.
A garden pathway surrounded by various flowering plants and a wooden structure in the background.
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.

8. Troutbeck

Troutbeck
Amenia
S$788
includes taxes & fees
27 Sept - 28 Sept
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 white building with a number '9' sign, a covered entrance, and six planters with shrubs.
A modern kitchen with a dining area, a sofa, and a TV mounted on the wall.

9. 9 Academy

9 Academy
Salisbury
S$831
includes taxes & fees
23 Sept - 24 Sept
9 Academy
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 dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.
A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

10. The White Hart

The White Hart
Salisbury
S$502
includes taxes & fees
15 Sept - 16 Sept
The White Hart
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Spacious, clean, and quiet. It was a little tricky to find the right building, but worth it."
Lynn 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"It was perfect for our weekend away, clean, comfortable bed and a decent breakfast, definitely worth the value:)"
Kimberly 2-night trip
Posted 16 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 21 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"Clean, staff was great, and ample parking"
Michael 3-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
sophia 1-night trip
Posted 6 days ago
Jiminy Peak Mountain Resort
Hotel On North

Hotel On North

10/10 Excellent
"Best place in town"
Mary Ellen 2-night trip
Posted 7 days ago
Hotel On North

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