Photo by Ed Gaffny

4 Stars Hotels in Cheshire, Massachusetts from CA $158

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Check availability on Cheshire 4 Star Hotels

Top Cheshire 4 Star Hotels

The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (485)
"The property was spacious but still had a cozy feel. "
The price is CA $298
CA $333 total
includes taxes & fees
Sep 7 - Sep 8
The Williams Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (300)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2
The Central Downtown Inn & Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (277)
"Great Views & Hospitality"
Lakehouse Inn
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
33 Main
Seven Hills Inn
Front of property

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
Seven Hills Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is CA $540
CA $653 total
includes taxes & fees
Aug 27 - Aug 28
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is CA $383
CA $428 total
includes taxes & fees
Sep 1 - Sep 2
Devonfield Inn B&B
Hampton Terrace Inn
Exterior

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is CA $453
CA $506 total
includes taxes & fees
Aug 17 - Aug 18
Hampton Terrace Inn
General Williams Estate House Lenox/Stockbridge
Exterior

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge
Garden Gables Inn
Front of property - evening/night

Garden Gables Inn

4.0 star property
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. "
Garden Gables Inn
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Learn more about Cheshire

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

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Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
" Beautiful hotel! "
Heather 2-night trip
Posted 3 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 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 $158

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.