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Luxury Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Luxury Hotels

Tonight
Sep 6 - Sep 7
Tomorrow
Sep 7 - Sep 8
Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

Our top choices for The Berkshires luxury hotels

1. The Williams Inn

The Williams Inn
Williamstown
P12,171
P13,595 total
includes taxes & fees
Sep 13 - Sep 14
The Williams Inn

2. Devonfield Inn B&B

Devonfield Inn B&B
Lee
P24,999
P27,924 total
includes taxes & fees
Sep 8 - Sep 9
Devonfield Inn B&B

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
P23,620
P27,703 total
includes taxes & fees
Sep 15 - Sep 16
The Inn at Stockbridge

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
P20,676
P24,950 total
includes taxes & fees
Sep 7 - Sep 8
The Old Inn On The Green

5. 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.
P20,687
P25,025 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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.
P6,203
P6,928 total
includes taxes & fees
Sep 7 - Sep 8
The Central Downtown Inn & Suites

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
P13,853
P15,474 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Terrace Inn

8. Troutbeck

Troutbeck
Amenia
P33,285
P40,160 total
includes taxes & fees
Oct 6 - Oct 7
Troutbeck

9. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
P14,975
P18,302 total
includes taxes & fees
Sep 8 - Sep 9
Simsbury 1820 House

10. The White Hart

The White Hart
Salisbury
P21,578
P24,815 total
includes taxes & fees
Sep 15 - Sep 16
The White Hart
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Enjoyed our stay and would highly recommend!"
Roger 2-night trip
Posted 7 hours ago
Vacation Village in the Berkshires
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Great little motel that was the perfect stay for a quick overnight trip"
Kate 1-night trip
Posted 8 hours ago
Willows Motel Williamstown
FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"The exterior is scary. The lobby is a fright. Rooms however were clean and updated. I appreciate that. But the lot is a disgrace."
Janet 1-night trip
Posted 3 days ago
FairBridge Inn Express
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."
Janet L. 2-night trip
Posted 4 days ago
Quality Inn Great Barrington

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