Compare and book 4 Star hotels in Chester, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Our top choices for Chester 4-star hotels

Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is 2.926.562 ₫
3.336.281 ₫ total
includes taxes & fees
5 Jul - 6 Jul
DoubleTree by Hilton Hotel Annapolis
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,000 reviews)
"Very fine place"
United States
David
The price is 4.818.299 ₫
5.492.861 ₫ total
includes taxes & fees
12 Jul - 13 Jul
Graduate by Hilton Annapolis
Lobby lounge

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Good location, nice hotel"
United States
Jiyoung
The price is 5.238.874 ₫
5.972.316 ₫ total
includes taxes & fees
5 Jul - 6 Jul
The Westin Annapolis
Premium bedding, down duvets, pillow-top 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, (938 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is 7.138.295 ₫
8.137.657 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Annapolis Waterfront Hotel, Autograph Collection
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, (463 reviews)
"Wonderful stay! Everything was amazing..,the staff, rooms, Knoxie’s Table, the spa! Couldn’t have asked for a better stay. I’ll definitely return."
United States
Damika
The price is 5.939.393 ₫
7.262.460 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is 11.582.552 ₫
12.740.807 ₫ total
includes taxes & fees
28 Jun - 29 Jun
The Oaks Waterfront
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 18.812.560 ₫ per night from 9 Jul to 10 Jul
18.812.560 ₫
20.693.815 ₫ total
9 Jul - 10 Jul
includes taxes & fees
9.6/10 Exceptional! (390 reviews)
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."
William 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection

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 favourite 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 10.216.121 ₫

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 accommodation. 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 travellers.