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Find Luxury Hotels in The Berkshires, MA

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Our top choices for The Berkshires luxury hotels

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ¥59,809
¥72,351 total
includes taxes & fees
Jan 20 - Jan 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (558)
"Great staff, great rooms, we had a little issue with the door not opening, but they were quick to fix it. Bar staff, fantastic! Restaurant (we had brunch) delicious. This is our go to hotel when we stay in the Berkshires "
United States
James
The price is ¥29,151
¥32,562 total
includes taxes & fees
Jan 12 - Jan 13
The Williams Inn

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ¥60,799
¥67,913 total
includes taxes & fees
Jan 18 - Jan 19
33 Main

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ¥28,814
¥33,794 total
includes taxes & fees
Jan 24 - Jan 25
Lakehouse Inn

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ¥47,763
¥57,637 total
includes taxes & fees
Jan 7 - Jan 8
The Old Inn On The Green

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is ¥37,396
¥43,860 total
includes taxes & fees
Jan 8 - Jan 9
The Inn at Stockbridge

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (351)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ¥14,720
¥16,443 total
includes taxes & fees
Jan 13 - Jan 14
The Central Downtown Inn & Suites

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is ¥34,280
¥38,291 total
includes taxes & fees
Jan 20 - Jan 21
Hampton Terrace Inn

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
The price is ¥77,321
¥88,920 total
includes taxes & fees
Jan 7 - Jan 8
9 Academy
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about The Berkshires

The Berkshiresand its attractions for luxury travelers

The Berkshires, a picturesque region in Massachusetts, offers luxury travelers an exquisite blend of culture, nature, and relaxation. Begin your journey at the renowned Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class performances in a stunning outdoor setting. For art enthusiasts, the Massachusetts Museum of Contemporary Art (MASS MoCA) is a must-visit, showcasing innovative installations and a vibrant arts scene. Nature lovers will revel in the serene beauty of the Bershires' rolling hills, perfect for hiking and exploring the Appalachian Trail, while the enchanting gardens at Naumkeag provide a peaceful retreat. After a day of adventure, unwind at the historic Wheatleigh Hotel, where luxurious accommodations and fine dining await, providing an ideal base to explore the region's charm. With attentive service and upscale amenities, your experience in The Berkshires is sure to be both memorable and rejuvenating.

Top The Berkshires Hotel Reviews

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