A person snowboarding down a snowy slope.

Luxury Hotels & Resorts in The Berkshires from NZ$197

  • 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

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for The Berkshires luxury hotels

1. Devonfield Inn B&B

Devonfield Inn B&B
Lee
NZ$734
includes taxes & fees
4 Nov - 5 Nov
Devonfield Inn B&B

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
Stockbridge
  • Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
NZ$718
includes taxes & fees
6 Nov - 7 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. The Williams Inn

The Williams Inn
Williamstown
NZ$346
includes taxes & fees
1 Nov - 2 Nov
The Williams Inn

4. 9 Academy

9 Academy
Salisbury
NZ$1,216
includes taxes & fees
12 Oct - 13 Oct
9 Academy

5. Troutbeck

Troutbeck
Amenia
NZ$1,110
includes taxes & fees
3 Nov - 4 Nov
Troutbeck

6. The White Hart

The White Hart
Salisbury
NZ$925
includes taxes & fees
7 Oct - 8 Oct
The White Hart

7. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
NZ$715
includes taxes & fees
30 Oct - 31 Oct
The Hermitage Inn Vermont

8. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
NZ$391
includes taxes & fees
2 Nov - 3 Nov
Simsbury 1820 House

9. The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel
Hudson
NZ$416
includes taxes & fees
1 Nov - 2 Nov
The Wick, Hudson, A Tribute Portfolio Hotel

10. The Four Chimneys Inn

The Four Chimneys Inn
Bennington
NZ$460
includes taxes & fees
1 Nov - 2 Nov
The Four Chimneys Inn
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"
Jennifer 1-night trip
Posted 12 hours ago
Vacation Village in the Berkshires
Hotel On North

Hotel On North

10/10 Excellent
"Beautiful boutique hotel. We will be back!"
Rebecca 1-night trip
Posted 17 hours ago
Hotel On North
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Beautiful location plenty of activities and very convenient having the country store on site! Also the onsite restaurant was amazing!"
Jeffrey 1-night trip
Posted 18 hours ago
Jiminy Peak Mountain Resort
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 22 hours ago
Quality Inn Great Barrington
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 6 days ago
Best Western Plus Berkshire Hills Inn & Suites

Explore a world of travel with Expedia