Chester Hotel Guide - 4 Stars Hotels in Chester, Maryland

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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 Rp1.979.805
Rp2.257.013 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 Rp3.259.556
Rp3.715.895 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 Rp3.542.996
Rp4.039.015 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 Rp5.142.466
Rp5.862.411 total
includes taxes & fees
5 Jul - 6 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 Rp4.016.750
Rp4.911.526 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 Rp7.831.139
Rp8.614.253 total
includes taxes & fees
21 Jun - 22 Jun
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
The price is Rp12.722.738 per night from 9 Jul to 10 Jul
Rp12.722.738
Rp13.995.012 total
9 Jul - 10 Jul
includes taxes & fees
9.6/10 Exceptional! (390 reviews)
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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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Chester awaits: its island views, sunny weather, golf and more!

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Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We had a girls trip for two nights and it was perfect. Quiet but beautiful, the pool was so nice and relaxing. Great food. Good spot. Would come back again!"
Michelle 2-night trip
Posted 7 hours ago
The Inn at Chesapeake Bay Beach Club

Frequently asked questions

What are the best 4-star hotels in Chester?
Expedia customers give top marks to The Inn at Chesapeake Bay Beach Club. From its handy amenities to its attentive staff, every aspect of this 4-star hotel in Chester is designed to deliver an incredible holiday experience.
How much does it cost to stay in a 4-star hotel in Chester?
To find a 4-star hotel in Chester that fits your budget, use Expedia's handy search filters. Take a look at the available options during your holiday dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly escape first.

  • Search for the lowest price from Rp6.907.275

What's the difference between 5-star and 4-star hotels in Chester?
If you choose to holiday at a 4-star hotel in Chester, you'll usually find plenty of amenities to keep you relaxed, such as a gym, restaurant and pool. You can enjoy top-quality service and upmarket accommodation. Opt for a 5-star hotel and you'll have access to a few extra perks — think on-site spas, 24-hour front desk and nightly turndown services. You're likely to get more amenities and first-class services at a 5-star retreat, though both are fabulous options for luxury guests.