A coastal town with a marina, a bridge, and a highway.

Chester 4 Stars Hotels

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Check availability on Chester 4 Star Hotels

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 modern living room with a sofa, armchairs, a coffee table, and a fireplace.

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
NT$3,402
NT$3,878 total
includes taxes & fees
Oct 18 - Oct 19
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 modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.
A spacious atrium with a high ceiling, skylights, and a patterned floor.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Mark
NT$4,686
NT$5,342 total
includes taxes & fees
Oct 26 - Oct 27
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.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
View from property

3. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
NT$6,353
NT$7,242 total
includes taxes & fees
Oct 26 - Oct 27
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.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

4. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
NT$7,178
NT$8,183 total
includes taxes & fees
Nov 2 - Nov 3
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 residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
NT$6,561
NT$8,101 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
NT$14,050
NT$15,455 total
includes taxes & fees
Oct 20 - Oct 21
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
NT$16,499
NT$18,148 total
Nov 9 - Nov 10
includes taxes & fees
Inn at Perry Cabin
The Inn at Tacaro Estate

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD
NT$11,251
NT$12,826 total
Nov 1 - Nov 2
includes taxes & fees
9.6/10 Exceptional! (20 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 coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"all good. Very good when it comes to parking during a boat show."
George 3-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."
Craig 1-night trip
Posted 1 day ago
The Inn at Chesapeake Bay Beach Club
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Easy parking. Super comfy bed."
Kristen 1-night trip
Posted 5 days ago
The Westin Annapolis

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 NT$12,826
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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