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.

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 AED 494

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Our top choices for Chester 4-star hotels

DoubleTree by Hilton Hotel Annapolis

Annapolis

Jehane

AED 494 total

includes taxes & fees

26 May - 27 May

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

Annapolis Waterfront Hotel, Autograph Collection

Historic District

Marie

AED 886 total

includes taxes & fees

25 May - 26 May

The Westin Annapolis

Annapolis

Jamise

AED 791 total

includes taxes & fees

24 May - 25 May

Graduate by Hilton Annapolis

Annapolis

Robert

AED 718 total

includes taxes & fees

31 May - 1 Jun

The Inn at Chesapeake Bay Beach Club

Stevensville

Kimberly

AED 1,013 total

includes taxes & fees

25 May - 26 May

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

The Oaks Waterfront

Easton

Jeffrey

AED 1,778 total

includes taxes & fees

17 May - 18 May

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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

AED 2,215

AED 2,436 total

31 May - 1 Jun

includes taxes & fees

9.6/10 Exceptional! (384 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!

See all hotels in Chester

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"GREAT LOCATION VERY CLEAN FACILITY"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"After a long day of travel, we decided the same day to book a stay in Annapolis as a middle point in our road trip. The hotel was so beautiful from the outside and just as lovely inside. I complimented both of the main desk staff members at check in and check out, it was notable how friendly and accommodating they were! My 6 year old said to me “this place has really great vibes”. 😂 if you’re looking for a conveniently located hotel in Annapolis with a nice harbor view and warm coastal energy, this is your place! "

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?

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 AED 1,263

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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