West Stockbridge Luxury Hotel

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Our top choices for West Stockbridge luxury hotels

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 HK$1,449
HK$1,699 total
includes taxes & fees
12 Dec - 13 Dec
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
The price is HK$695
HK$776 total
includes taxes & fees
11 Dec - 12 Dec
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
The price is HK$1,951
HK$2,289 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Inn at Stockbridge

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 HK$3,355
HK$3,747 total
includes taxes & fees
11 Dec - 12 Dec
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
The price is HK$2,045
HK$2,285 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hampton Terrace Inn

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 HK$1,978
HK$2,274 total
includes taxes & fees
10 Dec - 11 Dec
The White Hart

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 HK$2,971
HK$3,595 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

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 HK$2,373
HK$2,864 total
includes taxes & fees
10 Dec - 11 Dec
The Old Inn On The Green

9 Academy

4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
The price is HK$3,842
HK$4,418 total
includes taxes & fees
16 Dec - 17 Dec
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.

Top West Stockbridge Hotel Reviews

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Frequently asked questions

Are you searching for a great accommodation for your luxury trip to West Stockbridge?
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 holiday, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want a posh hotel that has a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that West Stockbridge has to offer. During your visit, you might want to enjoy the gardens which West Stockbridge is known for.
When can I expect good weather in West Stockbridge?
Planning for the weather is a good way to make your trip to West Stockbridge relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do in West Stockbridge?
Enjoy West Stockbridge and visit Stockbridge Bowl, Charles H. Baldwin & Sons and Hotchkiss Mobile Studio. If you have a little extra time during your trip, you might want to check out Ebenezer II Gifts and Antiques and Hoffman's Pottery.