Find Luxury Hotels in Williamstown, MA

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Check availability on Williamstown Luxury Hotels

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Williamstown luxury hotels

Front of property - evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (553)
"staff was great"
United States
Tim
The price is ￥32,828
￥36,668 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Williams Inn
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn
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 ￥26,544
￥31,133 total
includes taxes & fees
Dec 28 - Dec 29
Lakehouse Inn
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 ￥61,871
￥69,110 total
includes taxes & fees
Jan 18 - Jan 19, 2026
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 ￥59,557
￥72,048 total
includes taxes & fees
Jan 8 - Jan 9, 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

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
Reception
South Shire

South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (118)
"Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!"
United States
Roseann
The price is ￥26,166
￥30,223 total
includes taxes & fees
Dec 31 - Jan 1, 2026
South Shire
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 ￥39,110
￥45,872 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ￥14,658
￥16,373 total
includes taxes & fees
Dec 28 - Dec 29
The Central Downtown Inn & Suites
Exterior
Hampton Terrace Inn

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 ￥34,135
￥38,129 total
includes taxes & fees
Jan 3 - Jan 4, 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.
View all properties

Top Williamstown Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The bed was very comfortable. The staff was helpful and courteous"
Timothy 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

Are you searching for a great accommodation for your luxury getaway to Williamstown?
Use Expedia to arrange your flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Albany Intl. Airport (ALB) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Williamstown offers. During your visit, you might want to enjoy the museums and entertainment which Williamstown is known for.
When can I expect good weather in Williamstown?
Planning for the weather is an important factor for making your trip to Williamstown a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Williamstown 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 Williamstown?
Experience all that Williamstown has to offer when you visit Williams College Museum of Art, The Clark Art Institute, and Sterling and Francine Clark Art Institute. If you have a little extra time during your trip, you might want to make a stop at Williamstown Theatre Festival and Mount Greylock State Reservation.

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