A lake surrounded by autumn-colored trees and hills.

Search Luxury Hotels in Cheshire

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Luxury Hotels

Tonight
6 Aug - 7 Aug
Tomorrow
7 Aug - 8 Aug
This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Cheshire luxury hotels

1. The Williams Inn

The Williams Inn
Williamstown
₹22,560
₹25,199 total
includes taxes & fees
16 Aug - 17 Aug
The Williams Inn

2. 33 Main

33 Main
Lenox
₹67,243
₹75,111 total
includes taxes & fees
2 Sept - 3 Sept
33 Main

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
₹38,698
₹45,388 total
includes taxes & fees
12 Aug - 13 Aug
The Inn at Stockbridge

4. Devonfield Inn B&B

Devonfield Inn B&B
Lee
₹37,005
₹41,334 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B

5. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
  • Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
₹8,670
₹9,684 total
includes taxes & fees
3 Sept - 4 Sept
The Central Downtown Inn & Suites

6. 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
Stockbridge
  • Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
₹31,409
₹37,995 total
includes taxes & fees
24 Aug - 25 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
₹25,428
₹28,404 total
includes taxes & fees
3 Sept - 4 Sept
Hampton Terrace Inn
View all properties

Top Cheshire Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
Fausto 2-night trip
Posted 3 hours ago
Jiminy Peak Mountain Resort
The Yankee Inn

The Yankee Inn

8/10 Good
"Great standard hotel room. Clean and responsive housekeeping."
Monique 2-night trip
Posted 6 hours ago
The Yankee Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Need an extra chair in handicap rooms"
Thomas 3-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"We had an easy time finding it,close to shopping. Would stay again"
LYNN 1-night trip
Posted 3 days ago
Quality Inn Lee - Lenox South
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"My first time and I will go back."
Maribel 2-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Parking"
Wilson 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Lenox
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Room was clean and staff was nice. Air conditioner was a little noisy"
Susan 1-night trip
Posted 5 days ago
Hotel Downstreet, an Ascend Collection Hotel
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."
Michelle 2-night trip
Posted 10 days ago
FairBridge Inn Express

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 and Cheshire Reservoir, 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.

Explore a world of travel with Expedia