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Find luxury hotels in The Berkshires, MA

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Check availability on The Berkshires Luxury Hotels

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for The Berkshires luxury hotels

1. 33 Main

33 Main
Lenox
£517
includes taxes & fees
31 Aug - 1 Sept
33 Main

2. Devonfield Inn B&B

Devonfield Inn B&B
Lee
£319
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
£325
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge

4. The Williams Inn

The Williams Inn
Williamstown
£201
includes taxes & fees
14 Sept - 15 Sept
The Williams Inn

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.
£294
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
£283
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.
£75
includes taxes & fees
3 Sept - 4 Sept
The Central Downtown Inn & Suites

8. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
£181
includes taxes & fees
10 Sept - 11 Sept
Hampton Terrace Inn

9. Troutbeck

Troutbeck
Amenia
£438
includes taxes & fees
30 Aug - 31 Aug
Troutbeck

10. 9 Academy

9 Academy
Salisbury
£489
includes taxes & fees
24 Aug - 25 Aug
9 Academy
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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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 2 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 9 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 21 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 3 days ago
Jiminy Peak Mountain Resort
Hotel On North

Hotel On North

10/10 Excellent
"A great location for a concert at Tanglewood and a chance to explore a new city. Parking is easy and convenient. The staff is very welcoming and helpful. The facilities are clean, modern, quiet, and vintage at the same time. A beautiful bar and restaurant on site and many restaurants and coffee shops in walking distance. I would definitely stay here again!"
Amy 1-night trip
Posted 3 days ago
Hotel On North

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