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Best Luxury Hotels in The Berkshires

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Check availability on The Berkshires Luxury Hotels

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for The Berkshires luxury hotels

1. 33 Main

33 Main
Lenox
RM2,676
RM2,989 total
includes taxes & fees
31 Aug - 1 Sept
33 Main

2. The Williams Inn

The Williams Inn
Williamstown
RM1,061
RM1,185 total
includes taxes & fees
14 Sept - 15 Sept
The Williams Inn

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
RM1,522
RM1,786 total
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge

4. Devonfield Inn B&B

Devonfield Inn B&B
Lee
RM1,571
RM1,755 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B

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.
RM1,333
RM1,613 total
includes taxes & fees
7 Sept - 8 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
RM1,288
RM1,554 total
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green

7. 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.
RM405
RM452 total
includes taxes & fees
1 Sept - 2 Sept
The Central Downtown Inn & Suites

8. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
RM906
RM1,012 total
includes taxes & fees
21 Sept - 22 Sept
Hampton Terrace Inn

9. Troutbeck

Troutbeck
Amenia
RM2,107
RM2,545 total
includes taxes & fees
30 Aug - 31 Aug
Troutbeck

10. 9 Academy

9 Academy
Salisbury
RM2,398
RM2,758 total
includes taxes & fees
24 Aug - 25 Aug
9 Academy
View all properties

Find out more about The Berkshires

The Berkshiresand its attractions for luxury travelers

The Berkshires, a picturesque region in Massachusetts, offers a wealth of luxurious experiences for the discerning traveller. Begin your journey at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances under the stars while surrounded by the stunning natural beauty of the Berkshire hills. For art enthusiasts, the Norman Rockwell Museum in Stockbridge showcases the beloved works of America’s favourite illustrator, providing a glimpse into the cultural heart of the region. Those seeking relaxation can indulge in the serene atmosphere of Canyon Ranch, a wellness resort that offers spa treatments, fitness classes, and gourmet dining focused on health and well-being. For outdoor adventurers, the expansive hiking trails at Mount Greylock State Reservation promise breathtaking views, particularly in autumn when the foliage is ablaze with colour. Finally, indulge your palate at the acclaimed restaurants in Lenox, where farm-to-table dining experiences await, featuring the best local and seasonal ingredients. For a truly luxurious stay, consider the enchanting bluestone buildings of the Wheatleigh Hotel, a former Gilded Age mansion, where attentive service and elegant rooms make for an unforgettable retreat.

Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Such a charming hotel. Just stayed for the second time and it won’t be the last. Old school with modern amenities. A gem."
Carol 1-night trip
Posted 9 hours ago
Hotel On North
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 10 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Price - quality =awesome"
Anastasia 3-night trip
Posted 12 hours ago
Vacation Village in the Berkshires
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 1 day ago
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
Frank 2-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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