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Check availability on Great Barrington Luxury Hotels

Our top choices for Great Barrington luxury hotels

Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
The price is ₩449,036
₩541,861 total
includes taxes & fees
Apr 19 - Apr 20
The Old Inn On The Green
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (11 reviews)
The price is ₩782,133
₩899,453 total
includes taxes & fees
Apr 20 - Apr 21
9 Academy
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (149 reviews)
The price is ₩367,915
₩423,110 total
includes taxes & fees
Apr 19 - Apr 20
The White Hart
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is ₩322,276
₩359,980 total
includes taxes & fees
Apr 21 - Apr 22
Hampton Terrace Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
The price is ₩333,906
₩391,633 total
includes taxes & fees
Apr 17 - Apr 18
The Inn at Stockbridge
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (360 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is ₩150,170
₩167,734 total
includes taxes & fees
Apr 19 - Apr 20
The Central Downtown Inn & Suites
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
The price is ₩440,203
₩491,702 total
includes taxes & fees
Apr 22 - Apr 23
Devonfield Inn B&B
Suite, Private Bathroom (RedBird Suite) | View from room

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 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is ₩455,617
₩551,179 total
includes taxes & fees
Apr 29 - Apr 30
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is ₩727,292
₩812,386 total
includes taxes & fees
Apr 19 - Apr 20
33 Main
Hiking

The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel
4.0 star property
Hudson
8.8 out of 10, Excellent, (554 reviews)
The price is ₩307,700
₩347,701 total
includes taxes & fees
Apr 26 - Apr 27
The Wick, Hudson, A Tribute Portfolio Hotel
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.
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Top Great Barrington Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The room was comfortable, and clean. The staff was very courteous and helpful. Breakfast was adequate. Check in and check out went smoothly."
Sharon 2-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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.