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

Find 4 Star Hotels in Chester, MD from AED 409

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Check availability on Chester 4 Star Hotels

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

Our top choices for Chester 4-star hotels

Reception
Lobby
Lobby
Bar (on property)

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
eliana
AED 358
AED 409 total
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hotel Annapolis
View from property
Lobby
Bar (on property)
Lobby

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Patricia
AED 514
AED 586 total
includes taxes & fees
23 Aug - 24 Aug
Graduate by Hilton Annapolis
Premium bedding, down comforters, pillowtop beds, in-room safe
Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe
Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe
View from property

3. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
Stacey
AED 761
AED 868 total
includes taxes & fees
23 Aug - 24 Aug
Annapolis Waterfront Hotel, Autograph Collection
Lobby
Bar (on property)
Lobby
View from property

4. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Jessica
AED 621
AED 708 total
includes taxes & fees
16 Aug - 17 Aug
The Westin Annapolis
Front of property - evening/night
Garden
Ballroom
Lobby sitting area

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United Kingdom
Jamie
AED 792
AED 973 total
includes taxes & fees
31 Aug - 1 Sep
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
Indoor wedding
Smart TV
Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, WiFi (free), bed sheets

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
AED 1,616
AED 1,778 total
includes taxes & fees
16 Aug - 17 Aug
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
AED 1,821
AED 2,003 total
7 Sep - 8 Sep
includes taxes & fees
Inn at Perry Cabin
The Inn at Tacaro Estate

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD
AED 1,345
AED 1,533 total
23 Aug - 24 Aug
includes taxes & fees
The Inn at Tacaro Estate
Inn at 202 Dover

Inn at 202 Dover

202 East Dover Street Easton MD
Get ratesInn at 202 Dover
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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
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"The Graduate was extremely convenient to stay. Our son just completed Plebe summer and it was close to the Academy. Parking was included and easy to get in and out of. We had the Presidential Suite, with living room and a deck. We were able to let him relax.. The room was very clean, quiet and the staff was very helpful. It is a short walk or take the shuttle to the City Dock. I would stay there again in a second"
David 3-night trip
Posted 1 day 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 1,533
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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