Find Luxury Hotels in Chester, MA

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Our top choices for Chester luxury hotels

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
The price is ¥48,522
¥58,553 total
includes taxes & fees
Apr 12 - Apr 13
The Old Inn On The Green

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
The price is ¥47,568
¥53,133 total
includes taxes & fees
May 11 - May 12
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
The price is ¥39,900
¥46,798 total
includes taxes & fees
Apr 24 - Apr 25
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, (359 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is ¥16,227
¥18,125 total
includes taxes & fees
Apr 16 - Apr 17
The Central Downtown Inn & Suites

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is ¥34,825
¥38,899 total
includes taxes & fees
Apr 15 - Apr 16
Hampton Terrace Inn

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is ¥69,945
¥78,128 total
includes taxes & fees
Apr 23 - Apr 24
33 Main

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 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is ¥49,234
¥59,560 total
includes taxes & fees
Apr 24 - Apr 25
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 Pyramid Lake, Skyline Trail, and Jacob's Pillow. If you have spare time during your trip, you might want to make a stop at Otis Ridge and Chesterfield Gorge.

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