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Our top choices for Cheshire luxury hotels

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (291 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ₹13,242
₹15,531 total
includes taxes & fees
6 Feb - 7 Feb
Lakehouse Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (354 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ₹8,644
₹9,655 total
includes taxes & fees
15 Feb - 16 Feb
The Central Downtown Inn & Suites

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (571 reviews)
"Great stay. Comfortable hotel and very friendly staff. Restaurant is very good. "
United States
Veronica
The price is ₹16,954
₹18,937 total
includes taxes & fees
1 Mar - 2 Mar
The Williams Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134 reviews)
"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 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ₹21,959
₹25,755 total
includes taxes & fees
1 Feb - 2 Feb
The Inn at Stockbridge

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)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ₹28,458
₹34,426 total
includes taxes & fees
16 Feb - 17 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ₹35,817
₹40,008 total
includes taxes & fees
23 Feb - 24 Feb
33 Main

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is ₹20,129
₹22,484 total
includes taxes & fees
5 Feb - 6 Feb
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.

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 Mount Greylock. If you have a little extra time during your trip, you might want to make a stop at Wahconah Falls State Park and Brodie Mountain.

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