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Our top choices for Chester luxury hotels

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 ¥62,040
¥69,298 total
includes taxes & fees
Jan 18 - Jan 19, 2026
33 Main

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 ¥47,623
¥57,468 total
includes taxes & fees
Dec 28 - Dec 29
The Old Inn On The Green

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 ¥59,633
¥72,139 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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 ¥24,727
¥29,000 total
includes taxes & fees
Dec 28 - Dec 29
Lakehouse Inn

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

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 ¥39,160
¥45,931 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Inn at Stockbridge

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 ¥14,677
¥16,395 total
includes taxes & fees
Dec 28 - Dec 29
The Central Downtown Inn & Suites

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 ¥34,179
¥38,178 total
includes taxes & fees
Jan 11 - Jan 12, 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.

Find out more about Chester

Chesterand its attractions for luxury travelers

Chester, Massachusetts, a quaint gem nestled in the Berkshire Mountains, offers unique attractions that cater to the discerning luxury traveler. Begin your exploration at the picturesque Chester Blandford State Forest, where you can hike scenic trails lined with stunning foliage, perfect for a family adventure or a serene escape into nature. Just a short drive away, the iconic Berkshire Museum in Pittsfield showcases a remarkable collection of art, science, and history, making it an enriching experience for all ages. For a more leisurely outing, visit the historic Chester Town Hall, a charming venue that often hosts local arts and crafts fairs, allowing you to mingle with the community and discover unique handmade treasures. After a day of exploration, unwind at a luxurious hotel in the heart of the town, where you can expect attentive service and elegant rooms. Enjoy fine dining at nearby upscale restaurants that emphasize farm-to-table cuisine, ensuring a delightful culinary experience. Chester’s inviting atmosphere, coupled with its rich cultural offerings and natural beauty, makes it an appealing choice for families seeking both adventure and relaxation.

Top Chester Hotel Reviews

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Chester?
Use Expedia to help you arrange a flight to Westfield, MA (BAF-Barnes Municipal) airport or Pittsfield, MA (PSF-Pittsfield Municipal) airport, and then choose from a variety of places to stay that will deliver the luxury you want. 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 relaxing and comfortable. 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 Chester has to offer. Chester has some interesting things to see and do including Chester Town Hall, so you might want to take in the local sights during your visit.
When can I expect good weather in Chester?
Planning for the weather is a good way to make your trip to Chester 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 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What's there to see and do in Chester?
Experience Chester with a stop at Chester Town Hall, Pyramid Lake, and Blandford Ski Area. If you have spare time during your trip, you might want to make a stop at Jacob's Pillow and Otis Ridge.

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