Find Luxury Hotels in West Stockbridge, MA

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Check availability on West Stockbridge Luxury Hotels

Our top choices for West Stockbridge luxury hotels

Porch
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 SAR 699
SAR 819 total
includes taxes & fees
12 Dec - 13 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
11 Dec - 12 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 941
SAR 1,104 total
includes taxes & fees
1 Jan - 2 January 2026
The Inn at Stockbridge
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 1,619
SAR 1,809 total
includes taxes & fees
5 Jan - 6 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
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 954
SAR 1,097 total
includes taxes & fees
10 Dec - 11 Dec
The White Hart
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
5 Jan - 6 January 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
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
10 Dec - 11 Dec
The Old Inn On The Green
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
15 Dec - 16 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.
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Top West Stockbridge Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway 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 vacation, so we make it easy to find what you want to make your stay special. 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 temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge 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 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.