Photo by Elizabeth Massa Peroulakis

Find 4 Star Hotels in Chester, MA from SAR 473

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Compare Chester 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Lakehouse Inn
Lake

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 SAR 473
SAR 555 total
includes taxes & fees
1 Jan - 2 January 2025
Lakehouse Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (119)
"Great location "
The price is SAR 1,123
SAR 1,255 total
includes taxes & fees
6 Jan - 7 January 2025
Devonfield Inn B&B
33 Main
Room

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 SAR 1,367
SAR 1,527 total
includes taxes & fees
20 Jan - 21 January 2025
33 Main
The Central Downtown Inn & Suites
Exterior

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
Aerial view

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

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 SAR 995
SAR 1,157 total
includes taxes & fees
25 Dec - 26 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
View from room

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 SAR 1,594
SAR 1,928 total
includes taxes & fees
19 Jan - 20 January 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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!"
Hampton Terrace Inn
Garden Gables Inn
Front of property

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.

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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.