A person snowboarding down a snowy slope.

Find Luxury Hotels in The Berkshires

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Luxury Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for The Berkshires luxury hotels

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

1. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
The price is S$528
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A two-story house with a brick entrance and a white facade.

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (120 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is S$580
includes taxes & fees
13 Nov - 14 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.

3. The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.8 out of 10, Exceptional, (707 reviews)
The price is S$322
includes taxes & fees
8 Nov - 9 Nov
The Williams Inn
A modern kitchen with a dining area, a large window, and a view of the garden.

4. 9 Academy

9 Academy
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (15 reviews)
The price is S$822
includes taxes & fees
29 Nov - 30 Nov
9 Academy
A stone building with a wooden staircase and a garden with white flowers.

5. Troutbeck

Troutbeck
5.0 star property
Amenia
10.0 out of 10, Exceptional, (5 reviews)
The price is S$807
includes taxes & fees
24 Nov - 25 Nov
Troutbeck
A bedroom with a large bed, a chair, and a window with curtains.

6. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (156 reviews)
The price is S$439
includes taxes & fees
15 Nov - 16 Nov
The White Hart
An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.

7. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
4.5 star property
Hudson
8.6 out of 10, Excellent, (101 reviews)
The price is S$376
includes taxes & fees
29 Nov - 30 Nov
Pocketbook Hotel and Bath
A cozy room with a stone wall, a fireplace, and a table with a bottle of champagne in a crystal glass.

8. The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
9.0 out of 10, Wonderful, (20 reviews)
The price is S$492
includes taxes & fees
30 Oct - 31 Oct
The Hermitage Inn Vermont
A large, historic building with a covered porch and outdoor seating area.

9. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,003 reviews)
The price is S$286
includes taxes & fees
1 Nov - 2 Nov
Simsbury 1820 House
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

10. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (291 reviews)
The price is S$330
includes taxes & fees
19 Nov - 20 Nov
The Four Chimneys Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"What a charming place to stay after visiting the Berkshires! Beds are super comfy. Wish they had a smart TV though to connect to!"
Lidia 1-night trip
Posted 1 hour ago
Quality Inn Great Barrington

Explore a world of travel with Expedia