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 408

A boat docked at a pier during twilight with a city skyline in the background.

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Our top choices for Chester 4-star hotels

DoubleTree by Hilton Hotel Annapolis

Annapolis

Diane

SAR 408 total

includes taxes & fees

5 Jul - 6 Jul

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

Annapolis Waterfront Hotel, Autograph Collection

Historic District

Salvatore

SAR 1,015 total

includes taxes & fees

8 Jul - 9 Jul

The Westin Annapolis

Annapolis

Jiyoung

SAR 809 total

includes taxes & fees

1 Jul - 2 Jul

Graduate by Hilton Annapolis

Annapolis

David

SAR 733 total

includes taxes & fees

5 Jul - 6 Jul

The Inn at Chesapeake Bay Beach Club

Stevensville

Damika

SAR 1,036 total

includes taxes & fees

6 Jul - 7 Jul

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

The Oaks Waterfront

Easton

Jeffrey

SAR 1,818 total

includes taxes & fees

6 Jul - 7 Jul

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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 2,704

SAR 2,974 total

12 Jul - 13 Jul

includes taxes & fees

9.6/10 Exceptional! (391 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

Graduate by Hilton Annapolis

10/10 Excellent

"Convenient location. Beautiful property. Friendly staff!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."

Frequently asked questions

What are the best 4-star hotels in Chester?

Relax in upmarket comfort at The Inn at Chesapeake Bay Beach Club. According to reviews by our customers, this is one of Chester's favorite 4-star hotels.

How much does it cost to stay in a 4-star hotel in Chester?

Expedia can help you easily track down the ideal 4-star hotel for your getaway in Chester. Use our handy filter tool to fine-tune your search by things like budget, amenities and star rating and get access to fantastic deals in a few clicks.

Search for the lowest price from SAR 1,410

What's the difference between 5-star and 4-star hotels in Chester?

If you decide to stay at a 4-star hotel in Chester, you'll typically find plenty of amenities to keep you relaxed, such as a pool, restaurant and gym. You can enjoy high-quality service and upmarket accommodations. Opt for a 5-star hotel and you'll have access to a few more perks — think on-site spas, around-the-clock concierge and indulgent turndown services. You're likely to get extra amenities and first-class services at a 5-star retreat, though both are terrific options for luxury travelers.

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