The Best 4 Star Hotels in Chester, MD from $94 | Expedia

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.

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Tonight

Tomorrow

Feb 10 - Feb 11

This weekend

Feb 13 - Feb 15

Next weekend

Feb 20 - Feb 22

Our top choices for Chester 4-star hotels

Reception

DoubleTree by Hilton Hotel Annapolis

Annapolis

United States

Jose Miguel

$83 nightly

Feb 22 - Feb 23

Total with taxes and fees

Lobby

Graduate by Hilton Annapolis

Annapolis

United States

Brian

$165 nightly

Feb 22 - Feb 23

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Historic District

United States

Micah

$203 nightly

Feb 22 - Feb 23

Total with taxes and fees

Property amenity

The Westin Annapolis

Annapolis

United States

Robert

$169 nightly

Feb 15 - Feb 16

Total with taxes and fees

Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

Stevensville

United States

Alicia

$179 nightly

Feb 10 - Feb 11

Total with taxes and fees

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

Easton

United States

Seth

$459 nightly

Feb 13 - Feb 14

Total with taxes and fees

Save an average of 15% on thousands of hotels when you're signed in

Sign up, it's free

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

$513 nightly

$564 total

Feb 11 - Feb 12

Total with taxes and fees

9.4/10 Exceptional! (374 reviews)

Still don't see what you're looking for?

See all properties in Chester.

You can also use these popular filters to refine your search.

Pool Spa Hot tub Breakfast included Waterpark

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.

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Room was spotless. Staff was very courteous. Would highly recommended."

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 $330

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.

Explore a world of travel with Expedia

Things to do in Northern Chesapeake Bay

3b2d4d4b-5a0b-49ff-94f2-313b4186aebbcea7d800-cb22-47ff-b108-5c13cc9cfc67