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

Finding your dream vacation in Chester is as easy as entering your dates and destination, and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, food, activities and entertainment, or opt for a standard 4-star resort in or around this popular destination.

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

Enjoy the sights with ease when you check in to The Inn at Chesapeake Bay Beach Club . About 5 kilometers west from downtown Chester, this 4-star hotel offers the perfect spot to make the most of this buzzing city with the added convenience of Frette Italian sheets and a cafe.

The Best 4 Star Hotels in Chester, MD from SAR 327

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

Jose Miguel

SAR 327 total

includes taxes & fees

8 Feb - 9 Feb

Graduate by Hilton Annapolis

Annapolis

Brian

SAR 628 total

includes taxes & fees

15 Feb - 16 Feb

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

Annapolis Waterfront Hotel, Autograph Collection

Historic District

Micah

SAR 941 total

includes taxes & fees

8 Feb - 9 Feb

The Westin Annapolis

Annapolis

Robert

SAR 637 total

includes taxes & fees

30 Jan - 31 Jan

The Inn at Chesapeake Bay Beach Club

Stevensville

Alicia

SAR 745 total

includes taxes & fees

8 Feb - 9 Feb

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

The Oaks Waterfront

Easton

Seth

SAR 1,704 total

includes taxes & fees

28 Feb - 1 Mar

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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

SAR 1,789

SAR 1,968 total

27 Feb - 28 Feb

includes taxes & 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.

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

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