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Luxury Hotels & Resorts in The Berkshires from NZ$187

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Check availability on The Berkshires Luxury Hotels

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 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
NZ$1,164
includes taxes & fees
7 Sept - 8 Sept
33 Main

2. Devonfield Inn B&B

Devonfield Inn B&B
Lee
NZ$731
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
NZ$740
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge

4. The Williams Inn

The Williams Inn
Williamstown
NZ$454
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.
NZ$668
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
NZ$647
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.
NZ$187
includes taxes & fees
9 Sept - 10 Sept
The Central Downtown Inn & Suites

8. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
NZ$481
includes taxes & fees
10 Sept - 11 Sept
Hampton Terrace Inn

9. Troutbeck

Troutbeck
Amenia
NZ$1,060
includes taxes & fees
30 Aug - 31 Aug
Troutbeck

10. 9 Academy

9 Academy
Salisbury
NZ$1,108
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

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 11 hours 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 14 hours ago
Howard Johnson by Wyndham Lenox
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Easy, relaxed stay at a great hotel with excellent staff!"
Paul 2-night trip
Posted 17 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Hotel On North

Hotel On North

10/10 Excellent
"Charming and lovely and very well located! Staff were wicked friendly and helpful."
Margaret 1-night trip
Posted 19 hours ago
Hotel On North
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything was clean and well maintained. Very good included breakfast, close to Tanglewood, the Manor, the Norman Rockwell Museum, Lenox and Stockbridge."
Andrew 2-night trip
Posted 20 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Only real challenge—getting on the hotel wifi was a frustrating challenge! And every time you left your room you had to get on again."
Judith 4-night trip
Posted 21 hours ago
Quality Inn Great Barrington
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 21 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 2 days ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 5 days ago
Jiminy Peak Mountain Resort

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