Photo by Elizabeth Massa Peroulakis

4 Star Hotels in Chester, Massachusetts

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Top Chester 4 Star Hotels

Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (343)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
The price is €86
includes taxes & fees
23 Nov - 24 Nov
The Central Downtown Inn & Suites
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (288)
"Great Views & Hospitality"
United States
Gerald
The price is €174
includes taxes & fees
16 Nov - 17 Nov
Lakehouse Inn
Business centre
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)
"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"
United States
Carol Anne
The price is €399
includes taxes & fees
27 Nov - 28 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Seven Hills Inn

Seven Hills Inn

4.0 star property
Lenox
7.8 out of 10, Good, (467)
"Great location and grounds are really nice. "
United States
Angela
Seven Hills Inn
Exterior
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (110)
"This was a great place to house our family of 12 during the weekend of our daughter’s wedding. There was plenty of space for everyone to gather. The beds were comfortable and all the bedrooms upstairs had their own bathroom - so nice! The house made our weekend extra special. Definitely recommend!"
United States
Fern L.
General Williams Estate House Lenox/Stockbridge
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed
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)
"2nd stay here, even nicer than the first (and the first was amazing!). Can’t wait to return to this enchanting inn! "
United States
Walter
The price is €318
includes taxes & fees
16 Nov - 17 Nov
The Old Inn On The Green
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
The price is €254
includes taxes & fees
18 Nov - 19 Nov
The Inn at Stockbridge
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is €253
includes taxes & fees
17 Nov - 18 Nov
Hampton Terrace Inn
Luxury Room, 1 King Bed, Bathtub
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is €462
includes taxes & fees
23 Nov - 24 Nov
33 Main
Front of property – evening/night
Garden Gables Inn

Garden Gables Inn

4.0 star property
Lenox
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. "
United States
john
Garden Gables Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Chester

Experience the hiking, camping and forests in Chester!

See all hotels in Chester
Frozen Sanderson Brook Falls in Chester
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 €86

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.

Explore a world of travel with Expedia