Compare and book 4 Star hotels in Cheshire, Massachusetts

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Check availability on Cheshire 4 Star Hotels

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top 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, (546)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is 5.197.330 ₫
5.805.418 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Williams Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

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 2.354.395 ₫
2.629.909 ₫ total
includes taxes & fees
3 Dec - 4 Dec
The Central Downtown Inn & Suites
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is 4.851.896 ₫
5.690.547 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Lakehouse Inn
Front of property – evening/night
Devonfield Inn B&B

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
Front of property
Seven Hills Inn

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
Business centre
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, (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 10.069.321 ₫
12.181.017 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is 12.628.835 ₫
14.106.409 ₫ total
includes taxes & fees
14 Dec - 15 Dec
33 Main
Exterior
Hampton Terrace Inn

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 6.931.359 ₫
7.742.346 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Terrace Inn
Exterior
The Inn at Stockbridge

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 7.246.201 ₫
8.498.728 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Inn at Stockbridge
Front of property – evening/night
Garden Gables Inn

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.

See all hotels in Cheshire
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 2.629.909 ₫

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.

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