Cheshire Hotel Guide - 4 Stars Hotels in Cheshire, Massachusetts

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Check availability on Cheshire 4 Star Hotels

Tonight
31 Mar - 1 Apr
Tomorrow
1 Apr - 2 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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, (601 reviews)
"Amazing place to stay."
United States
Augusta
The price is Rp4.728.256
Rp5.281.462 total
includes taxes & fees
7 Apr - 8 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, (359 reviews)
"Clean room, easy checkin, loved the tea kettle. Clean, comfortable, would definitely return. "
United States
TIFFANY
The price is Rp1.853.218
Rp2.069.994 total
includes taxes & fees
2 Apr - 3 Apr
The Central Downtown Inn & Suites
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (297 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is Rp2.448.288
Rp2.871.474 total
includes taxes & fees
3 Apr - 4 Apr
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is Rp5.261.609
Rp6.365.174 total
includes taxes & fees
15 Apr - 16 Apr
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 Rp5.593.658
Rp6.248.065 total
includes taxes & fees
2 Apr - 3 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 Rp3.856.054
Rp4.522.702 total
includes taxes & fees
2 Apr - 3 Apr
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 Rp8.398.988
Rp9.381.669 total
includes taxes & fees
2 Apr - 3 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 Rp3.721.738
Rp4.157.159 total
includes taxes & fees
8 Apr - 9 Apr
Hampton Terrace Inn
Front of property – evening/night

Garden Gables Inn

Garden Gables Inn
4.0 star property
Lenox
9.2 out of 10, Wonderful, (57 reviews)
"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
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 lake views.

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
"The hotel is a great, upscale business hotel with friendly staff and a great restaurant."
Julie 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?
With Expedia's search and sort filters, locking in a superb deal on a 4-star hotel in Cheshire just got easier. Start by entering your chosen arrival date and length of your stay. Then sort the results by price and pick a property that best matches your style and budget.

  • Search for the lowest price from Rp2.069.994

What's the difference between 5-star and 4-star hotels in Cheshire?
Offering a welcoming traveller experience and upscale décor, 4-star hotels are a fantastic option for your Cheshire break. These kinds of accommodation generally feature lots of useful amenities that make it a breeze to unpack and unwind — think large beds, bathrobes, gyms and pools. Or get a taste of the high life at a 5-star hotel designed to spoil you with luxury perks and amenities. Full-service health clubs, premium toiletries and fine dining are typically included at these deluxe properties.
Does Cheshire have any 4-star all-inclusive resorts?
Enjoy a relaxing holiday experience where just about everything is included in the upfront price by using our "All inclusive" filter. Keeping to your budget is easy when your room, food and many activities are already taken care of. Eager for more ideas? Check out the terrific offers on our standard 4-star hotels in and around Cheshire.