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Our top choices for Cheshire luxury hotels
1. The Williams Inn
The Williams Inn4.0 star property
Williamstown
9.6 out of 10, Exceptional, (711 reviews)
9.6/10
Exceptional
(711 reviews)
The price is ₹18,953
₹18,953
₹21,171 total
includes taxes & fees
8 Nov - 9 Nov
2. Devonfield Inn B&B
Devonfield Inn B&B4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
10/10
Exceptional
(141 reviews)
The price is ₹34,925
₹34,925
₹39,011 total
includes taxes & fees
19 Nov - 20 Nov
3. 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 Chesterwood4.5 star property
Stockbridge
9.4 out of 10, Exceptional, (120 reviews)
9.4/10
Exceptional
(120 reviews)
- Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is ₹33,979
₹33,979
₹41,105 total
includes taxes & fees
6 Dec - 7 Dec
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.
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
Maple Terrace Motel
Maple Terrace MotelWilliamstown
10/10 Excellent
This was the BEST place we stayed in New England over a three week drive about.
This was the BEST place we stayed in New England over a three week drive about.
Norman
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCANorth Adams
10/10 Excellent
Nice stay with friendly welcoming staff
Nice stay with friendly welcoming staff
Martin
Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
10/10 Excellent
Perfect location and views. Comfortable and clean.
Perfect location and views. Comfortable and clean.
David
Williamstown Motel
Williamstown MotelWilliamstown
8/10 Good
Great location with easy parking
Great location with easy parking
David
Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
10/10 Excellent
On Mohawk Trail.
Limited space to eat if raining, but excellent choice for breakfast
On Mohawk Trail.
Limited space to eat if raining, but excellent choice for breakfast
Russell
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
Excellent room. All very clean.
Excellent room. All very clean.
Martin
Cozy Corner Motel
Cozy Corner MotelWilliamstown
10/10 Excellent
I have given it excellent under every heading simply because this was one of the nicest motels I've ever stayed in - lovely people, a good rate, and very well equipped, comfortable rooms. What more could one want?
I have given it excellent under every heading simply because this was one of the nicest motels I've ever stayed in - lovely people, a good rate, and very well equipped, comfortable rooms. What more could one want?
Peter
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
8/10 Good
The most unfriendly front desk staff on arrival out of the 6 hotels we've stayed in this vacation. Hotel is very modern but with questionable decorative style (i.e. Gaudy colour scheme and patterned carpets). Rooms are spacious and well equipped. Restaurant is a bit soulless but colleague working the bar, taking food orders, doing room service (ie. Everything!) is a bit of a star.
The most unfriendly front desk staff on arrival out of the 6 hotels we've stayed in this vacation. Hotel is very modern but with questionable decorative style (i.e. Gaudy colour scheme and patterned carpets). Rooms are spacious and well equipped. Restaurant is a bit soulless but colleague working the bar, taking food orders, doing room service (ie. Everything!) is a bit of a star.
Anonymous traveller
Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
10/10 Excellent
Excellent rooms in a great location
Excellent rooms in a great location
Alan
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
10/10 Excellent
Helpful staff, clean room and great facilities.
Helpful staff, clean room and great facilities.
Laura
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
10/10 Excellent
The hotel’s reception staff were exceptionally welcoming and helpful.
The hotel’s reception staff were exceptionally welcoming and helpful.
Emma
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.