Find 4 Star Hotels in Chester, MA from SAR 427

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Check availability on Chester 4 Star Hotels

Tonight
22 Feb - 23 Feb
Tomorrow
23 Feb - 24 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

Our top choices for Chester 4-star hotels

Terrace/patio

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (358 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is SAR 383
SAR 427 total
includes taxes & fees
24 Feb - 25 Feb
The Central Downtown Inn & Suites
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (293 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 535
SAR 627 total
includes taxes & fees
27 Feb - 28 Feb
Lakehouse Inn
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
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
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 SAR 1,161
SAR 1,404 total
includes taxes & fees
7 Mar - 8 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

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 SAR 1,705
SAR 1,904 total
includes taxes & fees
2 Mar - 3 Mar
33 Main
TV, fireplace, DVD player, video library

General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge
Stockbridge
9.8 out of 10, Exceptional, (115 reviews)
"Great place! I highly recommend!"
United States
jason w.
General Williams Estate House Lenox/Stockbridge
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is SAR 821
SAR 917 total
includes taxes & fees
23 Feb - 24 Feb
Hampton Terrace 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)
"Well-run and elegant property. "
United States
Steven
The price is SAR 896
SAR 1,051 total
includes taxes & fees
23 Feb - 24 Feb
The Inn at Stockbridge
Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is SAR 1,144
SAR 1,381 total
includes taxes & fees
23 Feb - 24 Feb
The Old Inn On The Green
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
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Learn more about Chester

Experience the hiking, camping, and waterfalls in Chester!

See all hotels in Chester
An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

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.

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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 accommodations. 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 vacation 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 accommodations, meals and activities, or go for a standard 4-star resort in or around this much-loved destination.