A lake surrounded by autumn-colored trees and hills.

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Check availability on Cheshire Luxury Hotels

Tonight
20 Sept - 21 Sept
Tomorrow
21 Sept - 22 Sept
Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct

Our top choices for Cheshire luxury hotels

1. The Williams Inn

The Williams Inn
Williamstown
₹17,693
₹19,763 total
includes taxes & fees
21 Oct - 22 Oct
The Williams Inn

2. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
₹20,987
₹23,443 total
includes taxes & fees
21 Sept - 22 Sept
Hampton Terrace Inn

3. 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.
₹9,399
₹10,498 total
includes taxes & fees
8 Oct - 9 Oct
The Central Downtown Inn & Suites

4. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
₹40,822
₹47,879 total
includes taxes & fees
22 Sept - 23 Sept
The Inn at Stockbridge

5. Devonfield Inn B&B

Devonfield Inn B&B
Lee
₹42,090
₹47,014 total
includes taxes & fees
21 Sept - 22 Sept
Devonfield Inn B&B

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.
₹49,517
₹59,902 total
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View all properties

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excelente A+, lo recomiendo"
Erick 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Hotel On North

Hotel On North

8/10 Good
"We loved staying there BUT we had two major hiccups: 1) the duvet covers are exceptionally heavy so we asked at the front desk for a blanket so we could use that instead. The answer we got back was that there had been some “event or something’ the day before and there were no blankets available. In that case, they brought us a second sheet and we used that instead of the duvet which worked out OK; 2) we stayed for two nights and they forgot to make up our room…which meant we came back to an unmade bed which was disappointing. We notified the front desk and while they were very apologetic they said the cleaning crew had left for the day so they couldn’t fix it. In general, it was clear they were short on staff. The youngish man on call to greet us could not have been less helpful and continued to be on other occasions. However, we encountered two other staff members and they were fine. Apart from that, we loved our room—very spacious with lots of character and the bathroom was also unusually large and well designed. Plugs are often a problem when we travel but our room had two perfectly placed plugs beside (not underneath!) each bed table (a big plus!). Parking behind the hotel is another huge plus—couldn’t be more convenient. We didn’t use the bar but did eat at the restaurant there one night (and their sister breakfast place down the street) and enjoyed both."
Linda 2-night trip
Posted 5 hours ago
Hotel On North
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
Dolores 3-night trip
Posted 5 days ago
Hotel Downstreet, 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'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, Cheshire Reservoir and Mount Greylock State Reservation Visitor Center. 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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