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Our top choices for Cheshire luxury hotels

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
United States
Janis
The price is ₹25,042
₹29,371 total
includes taxes & fees
21 May - 22 May
The Inn at Stockbridge

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"Very enjoyable comfortable stay"
United States
Christopher
The price is ₹25,579
₹28,571 total
includes taxes & fees
7 May - 8 May
Devonfield Inn B&B

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (622 reviews)
"Completely comfortable. Excellent restaurant. "
United States
Lisa
The price is ₹25,958
₹28,995 total
includes taxes & fees
13 May - 14 May
The Williams Inn

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, (111 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
"The Stockbridge Country Inn is the quintessential New England B&B! The owner, Diane, is the perfect host - very friendly and knowledgeable about the area. We stayed in The Maid's Suite which was extremely comfortable and beautifully decorated. Breakfast was always a delicious treat! The convenient location made access to sightseeing so easy."
United States
Linda
The price is ₹29,489
₹35,674 total
includes taxes & fees
25 May - 26 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Hot tub in the cottage was wonderful."
United States
Dee
The price is ₹28,196
₹31,495 total
includes taxes & fees
21 May - 22 May
Hampton Terrace Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (363 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
"We very much enjoyed the comfortable, large king bed and the cushy living room sofa."
United States
Angela
The price is ₹10,101
₹11,282 total
includes taxes & fees
31 May - 1 Jun
The Central Downtown Inn & Suites

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"We appreciate the larger room and renovate bathroom."
United States
Sirimon
The price is ₹62,094
₹69,359 total
includes taxes & fees
13 May - 14 May
33 Main
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.

Top Cheshire Hotel Reviews

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Cheshire?
Use Expedia to help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) 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 Cheshire has to offer. Cheshire has some interesting things to see and do including Mount Greylock State Reservation, so you might want to take in the local sights during your visit.
When can I expect good weather in Cheshire?
Planning for the weather is a good way to make your trip to Cheshire relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
What's there to see and do in Cheshire?
Enjoy all that Cheshire has to offer and visit Mount Greylock State Reservation, Mount Greylock State Reservation Visitor Center and Susan B. Anthony Birthplace Museum. If you have a little extra time during your trip, you might want to make a stop at Mount Greylock and Wahconah Falls State Park.

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