Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from $68

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Check availability on Chester 4 Star Hotels

Tonight
Dec 2 - Dec 3
Tomorrow
Dec 3 - Dec 4
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

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

Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1042)
"room was clean and quiet; parking was easy and safe. Very good welcome cookies too."
United States
Francisco
$60 nightly
The price is $68
Dec 21 - Dec 22
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1011)
"Nice big rooms, comfortable beds. Well maintained. "
United States
Margaret
$122 nightly
The price is $139
Dec 21 - Dec 22
Total with taxes and fees
Graduate by Hilton Annapolis
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (878)
"Clean room. Friendly staff awesome location. "
United States
Brent
$146 nightly
The price is $167
Dec 18 - Dec 19
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Great environment"
United States
Salvador E
$152 nightly
The price is $173
Dec 14 - Dec 15
Total with taxes and fees
The Westin Annapolis
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
$207 nightly
The price is $230
Dec 7 - Dec 8
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
$459 nightly
The price is $505
Dec 3 - Dec 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
$397 nightly
The price is $437 total per night from Dec 3 to Dec 4
$437 total
Dec 3 - Dec 4
Total with taxes and fees
9.4/10 Exceptional! (370 reviews)
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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
"Clean rooms, comfortable beds, friendly staff."
Nancy 2-night trip
Posted 4 days ago
Graduate by Hilton Annapolis

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.

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 $320

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.

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