Photo by Ed Gaffny

Cheshire 4 Stars Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire 4 Star Hotels

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Cheshire 4-star hotels

Front of property - evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (554)
"staff was great"
United States
Tim
The price is NT$6,884
NT$7,689 total
includes taxes & fees
Jan 11 - 2026/1/12
The Williams Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$2,955
NT$3,301 total
includes taxes & fees
Dec 28 - Dec 29
The Central Downtown Inn & Suites
Porch
Lakehouse Inn

Lakehouse Inn

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 NT$5,281
NT$6,194 total
includes taxes & fees
Dec 28 - Dec 29
Lakehouse Inn
Front of property - evening/night
Devonfield Inn B&B

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

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 center
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

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 NT$12,005
NT$14,523 total
includes taxes & fees
Jan 11 - 2026/1/12
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

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 NT$12,581
NT$14,054 total
includes taxes & fees
Jan 18 - 2026/1/19
33 Main
Exterior
Hampton Terrace Inn

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 NT$6,881
NT$7,686 total
includes taxes & fees
Jan 15 - 2026/1/16
Hampton Terrace Inn
Exterior
The Inn at Stockbridge

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 NT$7,884
NT$9,247 total
includes taxes & fees
Jan 5 - 2026/1/6
The Inn at Stockbridge
Front of property - evening/night
Garden Gables Inn

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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

The Williams Inn

The Williams Inn

10/10 Excellent
"Staff was courteous. Room was clean and felt...warm and inviting. Decor is classy cozy and clean. Every floor has coffee station with tea and coffee instead of in the room making it convenient before venturing out. The Barn is nice. I visited in winter so the ground, firepit and pool, were closed at 10 degrees. Gym is nice and has enough to get a good workout in and is clean."
Justin 2-night trip
Posted 5 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 NT$3,301

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.

Explore a world of travel with Expedia