Find Luxury Hotels in West Stockbridge, MA

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Check availability on West Stockbridge Luxury Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for West Stockbridge luxury hotels

Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

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 NT$12,581
NT$14,054 total
includes taxes & fees
Jan 18 - 2026/1/19
33 Main
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

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 NT$12,005
NT$14,523 total
includes taxes & fees
Jan 12 - 2026/1/13
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Porch
Lakehouse Inn

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 NT$5,375
NT$6,304 total
includes taxes & fees
Dec 30 - Dec 31
Lakehouse Inn
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

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 NT$9,587
NT$11,569 total
includes taxes & fees
Dec 30 - Dec 31
The Old Inn On The Green
Front of property - evening/night
Devonfield Inn B&B

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
Exterior
The Inn at Stockbridge

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 NT$7,884
NT$9,247 total
includes taxes & fees
Dec 30 - Dec 31
The Inn at Stockbridge
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (348)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$2,955
NT$3,301 total
includes taxes & fees
Dec 30 - Dec 31
The Central Downtown Inn & Suites
Hiking
The Wick, Hudson, A Tribute Portfolio Hotel

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, (547)
"Close to Warren street, friendly staff, pet friendly and clean. We will stay again! "
United States
Carell
The price is NT$6,601
NT$7,459 total
includes taxes & fees
Jan 8 - 2026/1/9
The Wick, Hudson, A Tribute Portfolio Hotel
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
9 Academy

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
The price is NT$15,521
NT$17,849 total
includes taxes & fees
Jan 5 - 2026/1/6
9 Academy
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi
The White Hart

The White Hart

The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (144)
"Great charming place, friendly, helpful staff"
United States
David
The price is NT$7,991
NT$9,189 total
includes taxes & fees
Jan 4 - 2026/1/5
The White Hart
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 & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too! "
Rakhee 2-night trip
Posted 22 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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.

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