Photo by Ed Gaffny

4 Star Hotels in Cheshire, Massachusetts

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Top Cheshire 4 Star Hotels

The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (371)
"A lovely hotel in close proximity to the Clark. Highly recommended!"
The price is €209
includes taxes & fees
1 Dec - 2 Dec
The Williams Inn
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is €177
includes taxes & fees
13 Dec - 14 Dec
Lakehouse Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (267)
"I loved all the amenities and space provided in the suite. And it was very affordable. It was like staying in an apartment. It was very clean. The bedroom wall was thin though because I could hear snoring on the other side. Pretty view of the trees in the backyard."
The Central Downtown Inn & Suites
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is €375
includes taxes & fees
25 Nov - 26 Nov
33 Main
Seven Hills Inn
Terrace/patio

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (117)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is €321
includes taxes & fees
5 Dec - 6 Dec
Devonfield Inn B&B
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is €533
includes taxes & fees
25 Nov - 26 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hampton Terrace Inn
Seasonal outdoor pool

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
Hampton Terrace Inn
Garden Gables Inn
Front of property – evening/night

Garden Gables Inn

4.0 star property
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
Garden Gables Inn
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Frequently asked questions

How much does it cost to stay in a 4-star hotel in Cheshire?
To lock in a 4-star hotel in Cheshire that matches your budget, make use of Expedia’s search and sort filters. Browse the availability during your travel dates and use our pricing filter to set your limit. You can also sort your results by the most affordable option first.

  • Search for the lowest price from €177

What's the difference between 5-star and 4-star hotels in Cheshire?
Treat yourself to refined living during your Cheshire holiday by choosing a 4-star hotel. As well as featuring upmarket accommodation, these properties are usually filled with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and special one. 24-hour concierge assistance, elegant décor and gourmet dining are just the start of the first-rate conveniences and services you’ll likely get access to.
Does Cheshire have any 4-star all-inclusive resorts?
Use our “All inclusive” filter to find your dream resort in Cheshire where just about everything is taken care of, from your accommodation to your food, entertainment and activities. We can also help you find standard 4-star stays in and around this destination.
Are there any 4-star casino hotels in Cheshire?
Shuffle between your room and the roulette wheel with ease by using our handy filter tool to find 4-star casino hotels in and around Cheshire. Getting away with someone special? Narrow your search further by choosing amenities with a wow-factor, like a pool or hot tub.