Find 4 Star Hotels in Cheshire, MA from SAR 374

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Compare Cheshire 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is SAR 710
SAR 793 total
includes taxes & fees
10 Dec - 11 Dec
The Williams Inn

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is SAR 335
SAR 374 total
includes taxes & fees
9 Dec - 10 Dec
The Central Downtown Inn & Suites

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 699
SAR 819 total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse Inn

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

Seven Hills Inn

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

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

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is SAR 1,433
SAR 1,734 total
includes taxes & fees
5 Jan - 6 January 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is SAR 1,636
SAR 1,827 total
includes taxes & fees
14 Dec - 15 Dec
33 Main

General Williams Estate House Lenox/Stockbridge

4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (111)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
United States
Joanna T.
General Williams Estate House Lenox/Stockbridge

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is SAR 987
SAR 1,102 total
includes taxes & fees
1 Jan - 2 January 2026
Hampton Terrace Inn

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is SAR 941
SAR 1,104 total
includes taxes & fees
1 Jan - 2 January 2026
The Inn at Stockbridge

Garden Gables Inn

4.0 star property
Lenox
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. "
United States
john
Garden Gables Inn
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Learn more about Cheshire

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

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

Top Cheshire Hotel Reviews

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 SAR 374

What's the difference between 5-star and 4-star hotels in Cheshire?
Treat yourself to refined living during your Cheshire vacation by choosing a 4-star hotel. As well as featuring upmarket accommodations, 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 accommodations to your food, entertainment and activities. We can also help you find standard 4-star stays in and around this destination.

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