A lake surrounded by autumn-colored trees and hills.

Luxury Hotels & Resorts in Cheshire from AU$139

  • 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
7 Sept - 8 Sept
Tomorrow
8 Sept - 9 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Cheshire luxury hotels

Front of property – evening/night
BBQ/picnic Area
Hallway
Restaurant

1. The Williams Inn

The Williams Inn
Williamstown
AU$295
includes taxes & fees
15 Sept - 16 Sept
The Williams Inn
Front of property – evening/night
Room #10 Queen's Cottage | Living room
Front of property – evening/night
Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly

2. Devonfield Inn B&B

Devonfield Inn B&B
Lee
AU$619
includes taxes & fees
8 Sept - 9 Sept
Devonfield Inn B&B
Front of property
The Fox Den in the Mainhouse
Lobby
Exterior

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
AU$614
includes taxes & fees
14 Sept - 15 Sept
The Inn at Stockbridge
Exterior
Deluxe Double Suite- NO PETS ALLOWED
Living area
Exterior

4. 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.
AU$154
includes taxes & fees
9 Sept - 10 Sept
The Central Downtown Inn & Suites
Suite, Private Bathroom (RedBird Suite) | View from room
Lobby sitting area
Breakfast area
Outdoor pool

5. 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.
AU$554
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail
Lobby sitting area
Fireplace
Staircase

6. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
AU$348
includes taxes & fees
10 Sept - 11 Sept
Hampton Terrace Inn
View all properties

Top Cheshire Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"This is a hidden gem in the Berkshires. The hotel is clean, rooms are gorgeous and the staff was really helpful."
Brian 1-night trip
Posted 1 hour ago
Hotel On North
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"A clean, comfortable room close to Tanglewood. No complaints."
Joanne 1-night trip
Posted 4 hours ago
Quality Inn Lee - Lenox South
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"The room was spotless and very comfortable. The bed was super comfortable and the shower was nice. The whole property was well kept and the country store is worth a look. We would definitely stay there again!"
Desiree 1-night trip
Posted 6 hours ago
Jiminy Peak Mountain Resort
FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"great value"
Horace 1-night trip
Posted 16 hours ago
FairBridge Inn Express
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"X"
Jonah 1-night trip
Posted 20 hours ago
Vacation Village in the Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"
Susan 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Great little motel that was the perfect stay for a quick overnight trip"
Kate 1-night trip
Posted 1 day ago
Willows Motel Williamstown

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.

Explore a world of travel with Expedia