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Find Luxury Hotels in Cheshire, MA

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Check availability on Cheshire Luxury Hotels

Tonight
Jul 8 - Jul 9
Tomorrow
Jul 9 - Jul 10
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Top Cheshire Luxury Hotels

We don't have any properties that match your exact search

Recommended hotels in Cheshire

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"We enjoyed our stay here very much. Nicely located between sites in the area we wanted to see (35 min from Lenox/Tanglewood and about the same to Mass MOCA to the north). Brandi was a wonderful host and I felt like I was staying with family (in the best possible way). Breakfast was filling and we enjoyed meeting other guests during that time. We stayed in the Garden Gate room and the bed was very comfortable. We would return here and recommend to our friends and family. "
Jessica
The price is NT$7,619
NT$8,053 total
includes taxes & fees
Jul 9 - Jul 10
Harbour House Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (101)
"Comfy bed in the Balcony room. Convenient parking and everything I needed for my stay. Such a beautiful old home with gorgeous stained glass windows. "
Deb
The price is NT$2,818
NT$4,281 total
includes taxes & fees
Jul 17 - Jul 18
Blooming Inn
UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
The price is NT$4,328
NT$4,575 total
includes taxes & fees
Jul 9 - Jul 10
UU Rowe Camp and Conference Center
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (57)
"Comfortable stay "
Paul
The price is NT$2,905
NT$4,218 total
includes taxes & fees
Jul 9 - Jul 10
Becket Motel
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (174)
"Beautiful views with nature activities. "
Joanne
The price is NT$6,108
NT$6,456 total
includes taxes & fees
Jul 9 - Jul 10
Blue Vista Motor Lodge
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.

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 and St Mary's of the Assumption Church, 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, St Mary's of the Assumption Church, 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.