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

Chester 4 Stars Hotels

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Check availability on Chester 4 Star Hotels

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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 DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
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.

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Fabiana
NT$3,085
NT$3,517 total
includes taxes & fees
Sep 27 - Sep 28
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 bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.
A spacious atrium with a high ceiling, skylights, and a patterned floor.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Patricia
NT$4,842
NT$5,519 total
includes taxes & fees
Sep 13 - Sep 14
Graduate by Hilton Annapolis
A balcony with a table set for two, overlooking a marina with boats.
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.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.

3. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
Deanna
NT$6,804
NT$7,757 total
includes taxes & fees
Sep 7 - Sep 8
Annapolis Waterfront Hotel, Autograph Collection
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A store with shelves of beverages, a counter with a cash register, and baskets with items.

4. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
susan greco
NT$5,617
NT$6,404 total
includes taxes & fees
Sep 13 - Sep 14
The Westin Annapolis
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
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
NT$6,870
NT$8,430 total
includes taxes & fees
Sep 28 - Sep 29
The Inn at Chesapeake Bay Beach Club
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A wooden console table with framed floral artwork, two lamps, and two ottomans.
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.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
NT$13,916
NT$15,307 total
includes taxes & fees
Sep 1 - Sep 2
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$19,074
NT$20,982 total
Sep 7 - Sep 8
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$12,541
NT$14,297 total
Aug 31 - Sep 1
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.

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A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"Lovely room, clean, comfortable, well appointed & quiet. We’d be happy to stay longer in such a nice room! We asked for early check-in, & were told we’d be contacted when the room was ready, but there was no follow-up contact. Our morning shower had no hot water so we washed quickly! We knew there was ongoing work with the water supply but didn’t expect cold showers. When we reported the issue at the front desk, we were graciously offered breakfast at the on-site restaurant. So glad we accepted! Food (& service & view) were excellent. We didn’t consider the restaurant previously because there was no evidence of it aside from a sign on the door. A posted menu could help. It’s a long walk down a cold hallway and we totally would have not considered it as a breakfast option. Definitely recommend eating at the restaurant!"
Anita 1-night trip
Posted 8 hours ago
Annapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Walking distance from the historic main street."
Daniel 1-night trip
Posted 4 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$14,297
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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