Find luxury hotels in Great Barrington, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Great Barrington Luxury Hotels

Our top choices for Great Barrington luxury hotels

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
$336 nightly
The price is $368
Dec 11 - Dec 12
Total with taxes and fees
The Old Inn On The Green

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
$195 nightly
The price is $218
Dec 12 - Dec 13
Total with taxes and fees
Lakehouse Inn

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
$85 nightly
The price is $95
Dec 11 - Dec 12
Total with taxes and fees
The Central Downtown Inn & Suites

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Inn at Stockbridge

The White Hart

4.0 star property
Salisbury
9.6 out of 10, Exceptional, (143)
"Great charming place, friendly, helpful staff"
United States
David
$254 nightly
The price is $292
Dec 11 - Dec 12
Total with taxes and fees
The White Hart

9 Academy

4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
$494 nightly
The price is $568
Dec 15 - Dec 16
Total with taxes and fees
9 Academy

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
$349 nightly
The price is $390
Dec 11 - Dec 12
Total with taxes and fees
Devonfield Inn B&B

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
$414 nightly
The price is $462
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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
$441 nightly
The price is $493
Dec 23 - Dec 24
Total with taxes and fees
33 Main

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
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Terrace Inn
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 Great Barrington

Great Barringtonand its attractions for luxury travelers

Great Barrington, Massachusetts, is a hidden gem for luxury travelers seeking a blend of relaxation and adventure. Start your day with a visit to the renowned Norman Rockwell Museum, where you can admire the iconic American artist's works in a stunning, serene setting. Afterward, savor a gourmet brunch at The Prairie Whale, known for its farm-to-table ethos and cozy atmosphere. For outdoor enthusiasts, the nearby Butternut Ski Area offers excellent skiing during the winter months, while hiking trails like Monument Mountain provide breathtaking views and a sense of accomplishment during warmer seasons. Don’t miss the vibrant local art scene showcased at the Mahaiwe Performing Arts Center, which often hosts high-caliber performances. When it comes to accommodations, the charming downtown area boasts luxurious hotels like the Hotel on North, where you’ll find beautifully appointed rooms and personalized service. This area not only puts you in nearby these attractions but also allows for leisurely strolls through quaint shops and galleries, enhancing your overall experience.

Find the best luxury hotels and resorts in Great Barrington

For travelers seeking a luxurious escape in Great Barrington, Massachusetts, these top hotels offer exquisite amenities and unparalleled comfort. Each hotel promises an indulgent experience perfect for a lavish getaway.

The Old Inn On The Green

  • Why it's great for a luxury retreat: The Old Inn On The Green is a sophisticated retreat that perfectly caters to luxury travelers, an impressive guest review rating of 9.6. Guests can indulge in the elegant ambiance enhanced by amenities such as deep soaking bathtubs, premium bedding, and cozy fireplaces, ensuring a relaxing and opulent stay.
  • Other amenities: This charming inn also features a beautiful terrace where guests can unwind while enjoying the scenic surroundings. A complimentary breakfast is offered daily, providing a delightful start to the day. The hotel includes self-parking options, daily housekeeping for convenience, and complimentary toiletries. Guests can also enjoy the serene garden area, perfect for leisurely strolls. For those interested in outdoor activities, ski locations are nearby, providing additional options for adventure.
  • Nearby attractions: Questing - 2.54 miles, Dry Hill - 2.77 miles, New Marlborough Town Hall - 3.34 miles

Top Great Barrington Hotel Reviews

Frequently asked questions

Are you looking for a luxury hotel for your Great Barrington vacation?
Expedia can help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are an important consideration when you plan a trip, so we make it easy to get what you'd like to make your stay special. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Great Barrington offers. During your visit, you might want to enjoy the live music which Great Barrington is known for.
When can I expect good weather in Great Barrington?
Planning for the weather is an important factor for making your trip to Great Barrington a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Great Barrington are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Great Barrington?
Enjoy all that Great Barrington has to offer when you visit Housatonic River Walk, Housatonic River, and Mahaiwe Performing Arts Center. If you have extra time while you're in the area, you might want to see Lake Mansfield Park and Ski Butternut.

Explore a world of travel with Expedia