Photo by Elizabeth Massa Peroulakis

4 Star Hotels in Chester, Massachusetts

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Top Chester 4 Star Hotels

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

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (321)
"Nice place "
The price is €99
includes taxes & fees
1 Oct - 2 Oct
The Central Downtown Inn & Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (283)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
The price is €173
includes taxes & fees
29 Sept - 30 Sept
Lakehouse 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 €320
includes taxes & fees
14 Oct - 15 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (89)
"Beautiful place to stay "
The price is €340
includes taxes & fees
29 Sept - 30 Sept
The Old Inn On The Green
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
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
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"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! "
The price is €591
includes taxes & fees
5 Oct - 6 Oct
33 Main
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 €293
includes taxes & fees
29 Sept - 30 Sept
Hampton Terrace Inn
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 price is €396
includes taxes & fees
29 Sept - 30 Sept
The Inn at 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
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 waterfalls in Chester!

See all hotels 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 €99

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

Explore a world of travel with Expedia