Compare and book 4 Star hotels in Cheshire, Massachusetts

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Check availability on Cheshire 4 Star Hotels

Tonight
21 Apr - 22 Apr
Tomorrow
22 Apr - 23 Apr
This weekend
24 Apr - 26 Apr
Next weekend
1 May - 3 May

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, (617 reviews)
"Amazing place to stay."
United States
Augusta
The price is 8.398.951 ₫
9.381.628 ₫ total
includes taxes & fees
29 Apr - 30 Apr
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, (360 reviews)
"Clean room, easy checkin, loved the tea kettle. Clean, comfortable, would definitely return. "
United States
TIFFANY
The price is 2.553.913 ₫
2.852.747 ₫ total
includes taxes & fees
30 Apr - 1 May
The Central Downtown Inn & Suites
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (298 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
Lakehouse Inn
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 8.149.274 ₫
9.858.496 ₫ total
includes taxes & fees
5 May - 6 May
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, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is 7.873.567 ₫
8.794.695 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is 6.920.312 ₫
8.116.620 ₫ total
includes taxes & fees
5 May - 6 May
The Inn at Stockbridge
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
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 15.347.701 ₫
17.143.382 ₫ total
includes taxes & fees
23 Apr - 24 Apr
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 5.763.418 ₫
6.437.704 ₫ total
includes taxes & fees
29 Apr - 30 Apr
Hampton Terrace Inn
Classic Queen - Room 8 | Premium bedding, down duvets, pillow-top beds, individually decorated

Garden Gables

Garden Gables
4.0 star property
Lenox
The price is 3.327.438 ₫
7.540.431 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Garden Gables
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 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

8/10 Good
"Clean room"
Amit 1-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 2.852.747 ₫

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.