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Check availability on Cheshire Luxury Hotels

Our top choices for Cheshire luxury hotels

Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (295 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is NT$4,596
NT$5,391 total
includes taxes & fees
Mar 20 - Mar 21
Lakehouse Inn
Front of property

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 NT$7,623
NT$8,940 total
includes taxes & fees
Mar 27 - Mar 28
The Inn at Stockbridge
Front of property - evening/night

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (592 reviews)
"Beautiful inn, wonderful staff."
United States
Susan
The price is NT$6,315
NT$7,054 total
includes taxes & fees
Mar 19 - Mar 20
The Williams Inn
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
50-inch flat-screen TV with cable channels, TV, streaming services

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (359 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$3,256
NT$3,637 total
includes taxes & fees
Mar 22 - Mar 23
The Central Downtown Inn & Suites
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is NT$7,014
NT$7,834 total
includes taxes & fees
Mar 22 - Mar 23
Hampton Terrace Inn
Suite, Private Bathroom (RedBird Suite) | View from room

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 NT$9,878
NT$11,950 total
includes taxes & fees
Apr 1 - Apr 2
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

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 NT$15,768
NT$17,613 total
includes taxes & fees
Mar 26 - Mar 27
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.
View all properties

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

6/10 Okay
"rooms have a weird smell, if the hotel is empty"
Clark 1-night trip
Posted 15 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 want 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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire 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 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 Brodie Mountain.

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