An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

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Check availability on Cheshire 4 Star Hotels

Our top choices for Cheshire 4-star hotels

Front of property – evening/night

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (631 reviews)
"Great property and restaurant. Perfect location and very helpful, friendly staff."
United States
Sam
The price is 8.660.596 ₫
9.673.885 ₫ total
includes taxes & fees
18 Jun - 19 Jun
The Williams Inn
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (370 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is 3.000.936 ₫
3.352.098 ₫ total
includes taxes & fees
14 Jun - 15 Jun
The Central Downtown Inn & Suites
Suite, Private Bathroom (RedBird Suite) | View from room

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is 8.691.395 ₫
10.514.065 ₫ total
includes taxes & fees
29 Jun - 30 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is 8.660.596 ₫
9.673.807 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Devonfield Inn B&B
Front of property

Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is 9.838.595 ₫
11.539.389 ₫ total
includes taxes & fees
23 Jun - 24 Jun
The Inn at Stockbridge
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (301 reviews)
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
United States
Angela
Lakehouse Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is 18.295.706 ₫
20.436.304 ₫ total
includes taxes & fees
14 Jun - 15 Jun
33 Main
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is 5.762.324 ₫
6.436.482 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Hampton Terrace Inn
Apartment (4 Bedrooms) | Interior

Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!
4.0 star property
Hancock
Family-friendly Hancock Home: Walk to Slopes!
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Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and wildlife.

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An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."
shawn 3-night trip
Posted 13 days ago
The Williams Inn

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 3.352.098 ₫

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.