An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

4 Stars Hotels in Cheshire, Massachusetts from CA $180

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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, (631 reviews)
"Great property and restaurant. Perfect location and very helpful, friendly staff."
United States
Sam
The price is CA $408
CA $456 total
includes taxes & fees
Jul 19 - Jul 20
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, (370 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 CA $161
CA $180 total
includes taxes & fees
Jun 21 - Jun 22
The Central Downtown Inn & Suites
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 CA $462
CA $559 total
includes taxes & fees
Jul 6 - Jul 7
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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $548
CA $613 total
includes taxes & fees
Jun 19 - Jun 20
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 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is CA $509
CA $597 total
includes taxes & fees
Jun 23 - Jun 24
The Inn at Stockbridge
Luxury Room, 1 King Bed, Bathtub

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 CA $892
CA $996 total
includes taxes & fees
Jul 1 - Jul 2
33 Main
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (302 reviews)
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
United States
Angela
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 CA $343
CA $383 total
includes taxes & fees
Jun 24 - Jun 25
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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Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and wildlife.

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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
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."
shawn 3-night trip
Posted 3 weeks ago
The Williams Inn

Find out more about Cheshire

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Cheshire are calling your name. Known for providing first-rate service in amazing locations, each of the Cheshire 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Cheshire. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Cheshire, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Cheshire hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Cheshire?
With Expedia's handy filter tool, bagging a great deal on a 4-star hotel in Cheshire just got simpler. Start by entering your chosen arrival date and length of your getaway. Then sort the results by price and choose a property that best suits your style and budget.

  • Search for the lowest price from CA $180

What's the difference between 5-star and 4-star hotels in Cheshire?
If you decide to vacation at a 4-star hotel in Cheshire, you'll typically find loads of conveniences to ensure you're relaxed, such as a restaurant, pool and gym. You can enjoy top-quality service and upscale surroundings. Opt for a 5-star hotel and you'll get a few extra perks — think on-site spas, around-the-clock concierge and opulent turndown services. You'll most likely get extra amenities and first-class services at a 5-star stay, but both are fabulous options for luxury guests.
Does Cheshire have any 4-star all-inclusive resorts?
Enjoy a carefree vacation experience where just about everything is included in the upfront price by using our "All inclusive" filter. Budgeting is simple when your accommodations, food and many activities are already taken care of. Want more options? Browse the amazing deals on our standard 4-star options in and around Cheshire too.

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