Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from $131

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

Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1008)
"Great area and it was a perfect hotel for our trip. "
$178 nightly
The price is $203
Sep 9 - Sep 10
Total with taxes and fees
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1009)
"Nice hotel, convenient location with easy parking. "
$115 nightly
The price is $131
Sep 28 - Sep 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1008)
"Would stay there again very soon "
$199 nightly
The price is $227
Sep 4 - Sep 5
Total with taxes and fees
The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (859)
"Easy check in, clean and close to everything "
$237 nightly
The price is $270
Sep 28 - Sep 29
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (416)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
$248 nightly
The price is $275
Oct 1 - Oct 2
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"The facility designed was out standing and the staff was very good. "
$459 nightly
The price is $505
Sep 3 - Sep 4
Total with taxes and fees
The Oaks Waterfront
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD
$629 nightly
The price is $692 total per night from Sep 7 to Sep 8
$692 total
Sep 7 - Sep 8
Total with taxes and fees
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Chester

Chester awaits: its island views, sunny weather, golf, and more!

See all hotels in Chester
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"There were two great guys at the bar; they were fun, friendly, and good company. The staff at the front desk was very knowledgeable and friendly."
Michele 3-night trip
Posted 3 days ago
Graduate by Hilton Annapolis

Find out more about Chester

Find out more about Chester

Chester Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chester, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chester, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chester hotels offer everything your heart desires.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What are the best 4-star hotels in Chester?
Expedia customers highly rate The Inn at Chesapeake Bay Beach Club. From its handy amenities to its welcoming staff, everything about this 4-star hotel in Chester is designed to provide an exceptional vacation experience.
How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's filter tool, scoring an awesome deal on a 4-star hotel in Chester just got simpler. Start by entering your chosen arrival date and length of your escape. Then list the results by price and pick a property that best matches your budget and style.

  • Search for the lowest price from $465

What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveler experience and upmarket décor, 4-star hotels are a fabulous option for your Chester getaway. These kinds of stays generally feature lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to pamper with luxury perks and amenities. Round-the-clock concierge service, premium toiletries and world-class dining are typically included at these deluxe retreats.