Photo by Elizabeth Massa Peroulakis

4 Star Hotels in Chester, Massachusetts

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Top Chester 4 Star Hotels

Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"We really enjoyed our stay. The breakfast was really good and the added touch of a welcome drink was really fun and made our stay feel special. We would like to come back again. "
The price is €142
includes taxes & fees
29 Dec - 30 Dec
Lakehouse Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (119)
"It was a great last minute trip. The property is very well maintained and decorated for the holidays. I wish Doug and Tim a great holiday season and Happy New Year. We will be back!!"
The price is €342
includes taxes & fees
5 Jan - 6 Jan 2025
Devonfield Inn B&B
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"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 €390
includes taxes & fees
20 Jan - 21 Jan 2025
33 Main
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (269)
"The suite we stayed in was spacious. Maid service is only once weekly, but when we contacted them about getting additional toilet paper, they were very responsive. The queen bed in the bedroom was very comfortable. We were not able to get the TV in the bedroom to work. The sofa queen bed in the living room was all broken down. My husband had to put boards under the mattress to support it enough so he could use the bed. The kitchen was clean and well-stocked."
The Central Downtown Inn & Suites
Seven Hills Inn
Terrace/patio

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
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, (80)
"2nd stay here, even nicer than the first (and the first was amazing!). Can’t wait to return to this enchanting inn! "
The price is €295
includes taxes & fees
24 Dec - 25 Dec
The Old Inn On The Green
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
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)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is €492
includes taxes & fees
5 Jan - 6 Jan 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hampton Terrace Inn
Seasonal outdoor pool

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!"
Hampton Terrace Inn
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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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 €142

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.
Are there any 4-star casino hotels in Chester?
Shuffle between your room and the poker table with ease by using our handy filter tool to find 4-star casino hotels in and around Chester. Getting away with someone special? Refine your search further by choosing amenities with that wow-factor, like a hot tub or view.