Find Luxury Hotels in Great Barrington, MA

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Check availability on Great Barrington Luxury Hotels

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Great Barrington Luxury Hotels

Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
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 SAR 1,145
SAR 1,381 total
includes taxes & fees
8 Dec - 9 Dec
The Old Inn On The Green
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 699
SAR 819 total
includes taxes & fees
19 Dec - 20 Dec
Lakehouse Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

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
The price is SAR 335
SAR 374 total
includes taxes & fees
8 Dec - 9 Dec
The Central Downtown Inn & Suites
Exterior
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 SAR 986
SAR 1,157 total
includes taxes & fees
21 Dec - 22 Dec
The Inn at Stockbridge
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi
The White Hart

The White Hart

4.0 star property
Salisbury
9.6 out of 10, Exceptional, (143)
"Great charming place, friendly, helpful staff"
United States
David
The price is SAR 1,060
SAR 1,219 total
includes taxes & fees
9 Dec - 10 Dec
The White Hart
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
9 Academy

9 Academy

4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
The price is SAR 1,853
SAR 2,131 total
includes taxes & fees
16 Dec - 17 Dec
9 Academy
Front of property - evening/night
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
Business center
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 SAR 1,433
SAR 1,734 total
includes taxes & fees
6 Jan - 7 January 2026
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)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is SAR 1,602
SAR 1,789 total
includes taxes & fees
6 Jan - 7 January 2026
33 Main
Exterior
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 SAR 987
SAR 1,102 total
includes taxes & fees
1 Jan - 2 January 2026
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.
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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
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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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.