Chester Hotel Guide - 4 Stars Hotels in Chester, Maryland

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Check availability on Chester 4 Star Hotels

Tonight
7 Mar - 8 Mar
Tomorrow
8 Mar - 9 Mar
Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar

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, (1,014 reviews)
"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "
United States
Kathy
The price is Rp1.512.757
Rp1.724.543 total
includes taxes & fees
15 Mar - 16 Mar
DoubleTree by Hilton Hotel Annapolis
Lobby

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,002 reviews)
"Room was clean, great location"
United States
Brian
The price is Rp2.841.731
Rp3.239.573 total
includes taxes & fees
15 Mar - 16 Mar
Graduate by Hilton 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, (906 reviews)
"Great location, nice and clean "
United States
Micah
The price is Rp3.582.176
Rp4.083.682 total
includes taxes & fees
29 Mar - 30 Mar
Annapolis Waterfront Hotel, Autograph Collection
Property amenity

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is Rp3.029.575
Rp3.453.715 total
includes taxes & fees
8 Mar - 9 Mar
The Westin Annapolis
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, (439 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is Rp2.804.332
Rp3.542.871 total
includes taxes & fees
8 Mar - 9 Mar
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, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is Rp7.439.891
Rp8.183.880 total
includes taxes & fees
8 Mar - 9 Mar
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 Rp6.263.302 per night from 8 Mar to 9 Mar
Rp6.263.302
Rp6.889.632 total
8 Mar - 9 Mar
includes taxes & fees
9.6/10 Exceptional! (374 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.

Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I stayed here as I did a visit for my youngest son who is attending Bowie. While I stayed most of the time on campus, I found when I was at the hotel I found the staff and facility both inviting, warm and cordial. "
Kent Andrew 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

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 Rp6.889.632

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.