Cheshire Hotel Guide - 4 Stars Hotels in Cheshire, Massachusetts

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Check availability on Cheshire 4 Star Hotels

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, (627 reviews)
"Amazing place to stay."
United States
Augusta
The price is Rp4.921.001
Rp5.496.758 total
includes taxes & fees
21 May - 22 May
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, (365 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is Rp2.006.058
Rp2.240.802 total
includes taxes & fees
1 Jun - 2 Jun
The Central Downtown Inn & Suites
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is Rp4.733.593
Rp5.287.371 total
includes taxes & fees
18 May - 19 May
Devonfield Inn B&B
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 Rp5.445.744
Rp6.587.930 total
includes taxes & fees
31 May - 1 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 Rp4.624.492
Rp5.423.923 total
includes taxes & fees
21 May - 22 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 Rp11.607.333
Rp12.965.391 total
includes taxes & fees
18 May - 19 May
33 Main
Double Room, 1 Queen Bed, Private Bathroom, Lake View | Iron/ironing board, free WiFi, bed sheets

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (299 reviews)
"Staff wonderful, homemade breakfasts, outstanding experience!"
United States
Kathleen
Lakehouse Inn
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 Rp4.819.818
Rp5.383.626 total
includes taxes & fees
25 May - 26 May
Hampton Terrace 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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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 very helpful. Rooms were great. Unbeatable location for Williamstown (especially if you’re in town for an athletic event at Williams). Really solid breakfast with friendly and attentive wait staff. Only minor complaint is that the WiFi is not great. Other than that it was a perfect stay."
Jason 3-night trip
Posted 7 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 Rp2.240.802

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.