Does Chester have any 4-star all-inclusive resorts?

Finding your dream hotel in Chester is as simple as entering your travel dates and destination, and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your room, meals and activities, or opt for a standard 4-star resort in or around this sought-after destination.

Are there any 4-star casino hotels in Chester?

Shuffle between your room and the slot machines with ease by using our handy filters to find 4-star casino hotels in and around Chester. Celebrating with someone special? Refine your search further by selecting amenities with a wow-factor, like a pool or view.

What are the top 4-star hotels in downtown Chester?

Situated around 3 mi west from the heart of Chester, The Inn at Chesapeake Bay Beach Club will put you close to the action. This 4-star hotel also has a cafe and a pillowtop mattress for your convenience.

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

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.

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Our top choices for Chester 4-star hotels

DoubleTree by Hilton Hotel Annapolis

Annapolis

Kathy

$83 nightly

Feb 22 - Feb 23

Total with taxes and fees

Graduate by Hilton Annapolis

Annapolis

Brian

$161 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

Micah

$203 nightly

Feb 22 - Feb 23

Total with taxes and fees

The Westin Annapolis

Annapolis

Robert

$179 nightly

Feb 22 - Feb 23

Total with taxes and fees

The Inn at Chesapeake Bay Beach Club

Stevensville

Alicia

$179 nightly

Feb 16 - Feb 17

Total with taxes and fees

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

The Oaks Waterfront

Easton

Seth

$459 nightly

Feb 16 - Feb 17

Total with taxes and fees

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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

308 Watkins Ln St. Michaels MD

$513 nightly

$564 total

Feb 18 - Feb 19

Total with taxes and fees

9.4/10 Exceptional! (374 reviews)

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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!

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Top Chester Hotel Reviews

The Westin Annapolis

10/10 Excellent

"The staff was wonderful, Room was spotless. Bar prices were insane for the area."

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 $369

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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Things to do in Northern Chesapeake Bay

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