Photo by Elizabeth Massa Peroulakis

4 Star Hotels in Chester, Massachusetts

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Check availability on Chester 4 Star Hotels

Tonight
5 Aug - 6 Aug
Tomorrow
6 Aug - 7 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Chester 4 Star Hotels

The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (299)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is €111
includes taxes & fees
1 Sept - 2 Sept
The Central Downtown Inn & Suites
Lakehouse Inn
Relax on the deck with a glass of wine, taking in the serene views of the surrounding water and lush landscape.

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (276)
"Great Views & Hospitality"
Lakehouse Inn
33 Main
Features a sleek glass-enclosed shower, vanity with sink and mirror, toilet, and bidet.

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
The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (88)
"Beautiful room and property. Perfect weekend getaway!"
The price is €302
includes taxes & fees
14 Aug - 15 Aug
The Old Inn On The Green
Seven Hills Inn
Enjoy meals in this elegant dining area with a central round table and comfortable seating.

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 Inn at Stockbridge
Stroll through the serene park and enjoy the soothing sounds of the multi-tiered fountain surrounded by lush trees and a shaded walkway.

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
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Hampton Terrace Inn
Welcome to this charming two-story house with a cozy front porch and balcony, featuring a wreath above the door and green shutters.

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 €296
includes taxes & fees
3 Sept - 4 Sept
Hampton Terrace Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

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 €410
includes taxes & fees
18 Aug - 19 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
General Williams Estate House Lenox/Stockbridge
Two houses sit amidst a well-manicured lawn and lush trees.

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
Stunning mountain retreat with a spacious porch and multiple windows, surrounded by snow-covered trees and a well-lit pathway.

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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Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
Expedia can help you easily find the ideal 4-star hotel for your getaway in Chester. Use our filter tool to tailor your search by things like budget, conveniences and star rating and get access to unbeatable deals in a few clicks.

  • Search for the lowest price from €111

What's the difference between 5-star and 4-star hotels in Chester?
If you decide to book a stay at a 4-star hotel in Chester, you'll typically find loads of conveniences to ensure you're comfortable, such as a restaurant, gym and pool. You can enjoy top-quality service and upscale accommodation. Opt for a 5-star hotel and you'll have access to a few more perks — think on-site spas, concierge assistance and nightly turndown services. You're likely to get additional amenities and first-class services at a 5-star stay, though both are awesome options for luxury guests.
Does Chester have any 4-star all-inclusive resorts?
Finding holiday bliss in Chester is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodation, meals and activities, or go for a standard 4-star resort in or around this much-loved destination.