Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from AED 244

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Check availability on Chester 4 Star Hotels

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Compare Chester 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1040)
"Room was comfortable and the staff were courtesy!"
United States
Danny
The price is AED 214
AED 244 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Hotel Annapolis
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1010)
"Nice big rooms, comfortable beds. Well maintained. "
United States
Margaret
The price is AED 449
AED 512 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (878)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is AED 537
AED 613 total
includes taxes & fees
18 Dec - 19 Dec
Annapolis Waterfront Hotel, Autograph Collection
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1006)
"Great environment"
United States
Salvador E
The price is AED 559
AED 637 total
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is AED 675
AED 843 total
includes taxes & fees
3 Dec - 4 Dec
The Inn at Chesapeake Bay Beach Club
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is AED 1,517
AED 1,669 total
includes taxes & fees
2 Dec - 3 Dec
The Oaks Waterfront
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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

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
The price is AED 1,325 per night from Dec 4 to Dec 5
AED 1,325
AED 1,603 total
4 Dec - 5 Dec
includes taxes & fees
9.4/10 Exceptional! (370 reviews)
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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.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean rooms, comfortable beds, friendly staff."
Nancy 2-night trip
Posted 3 days ago
Graduate by Hilton Annapolis

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 1,603

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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