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

Find 4 Star Hotels in Chester, MD from AED 406

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Check availability on Chester 4 Star Hotels

Tonight
29 Sep - 30 Sep
Tomorrow
30 Sep - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chester 4-star hotels

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A restaurant with wooden tables and chairs, a bar area, and a tiled floor.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
AED 356
AED 406 total
includes taxes & fees
1 Oct - 2 Oct
DoubleTree by Hilton Hotel Annapolis
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.
A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.
A spacious atrium with a high ceiling, skylights, and a patterned floor.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
princess
AED 539
AED 615 total
includes taxes & fees
26 Oct - 27 Oct
Graduate by Hilton Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
View from property
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

3. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
AED 731
AED 833 total
includes taxes & fees
25 Oct - 26 Oct
The Westin Annapolis
A balcony with a table set for two, overlooking a marina with boats.
A waterfront area with boats docked, a clear sky, and buildings in the background.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

4. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
AED 996
AED 1,135 total
includes taxes & fees
25 Oct - 26 Oct
Annapolis Waterfront Hotel, Autograph Collection
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
AED 702
AED 873 total
includes taxes & fees
19 Oct - 20 Oct
The Inn at Chesapeake Bay Beach Club
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
AED 1,616
AED 1,778 total
includes taxes & fees
30 Sep - 1 Oct
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 1,884
AED 2,073 total
26 Oct - 27 Oct
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 1,457
AED 1,661 total
4 Oct - 5 Oct
includes taxes & fees
9.6/10 Exceptional! (19 reviews)
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Staff friendly, clean room. The Bar and Restaurant was enjoyable."
michael 1-night trip
Posted 16 hours ago
DoubleTree by Hilton Hotel Annapolis
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Good stay. I wish I could have used the spa. It was closed on tuesdays. I also wish they could have provided free breakfast for the price that they charge per room"
Rathna 1-night trip
Posted 4 days ago
The Inn at Chesapeake Bay Beach Club
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 8 days ago
The Westin 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 1,661
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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