Photo by Patricia Knorr

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Check availability on Chester 4 Star Hotels

Tonight
Jul 24 - Jul 25
Tomorrow
Jul 25 - Jul 26
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Compare Chester 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

DoubleTree by Hilton Hotel Annapolis
Welcome to DoubleTree by Hilton, featuring a traditional brick facade and a distinctive peaked roof.

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1011)
"Excellent hospitable staff made the stay even better!"
$99 nightly
The price is $112
Aug 3 - Aug 4
Total includes taxes and fees
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
Enjoy serene sailing and stunning views of the marina, surrounded by historic landmarks.

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Loved the location and the nautical decor "
$155 nightly
The price is $177
Aug 3 - Aug 4
Total includes taxes and fees
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Relax in this serene room with a large bed, a comfortable armchair, and a floor lamp, offering a view of the nearby water.

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (843)
"Front desk staff was very friendly and helpful."
$220 nightly
The price is $251
Aug 17 - Aug 18
Total includes taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis
Experience the grandeur of this classic hotel, featuring a symmetrical facade with a central entrance and evenly spaced windows.

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Easy downtown location, walkable to waterfront and great restaurants "
$159 nightly
The price is $181
Aug 10 - Aug 11
Total includes taxes and fees
The Westin Annapolis
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (402)
"Staff was very polite and friendly. "
$228 nightly
The price is $253
Aug 24 - Aug 25
Total includes taxes and fees
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
Stately home with a central entrance and two wings, set amidst manicured lawns and shaded by trees.

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
$459 nightly
The price is $505
Jul 27 - Jul 28
Total includes taxes and fees
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
$698 nightly
The price is $768 total per night from Aug 6 to Aug 7
$768 total
Aug 6 - Aug 7
Total includes taxes and fees
9.4/10 Exceptional! (355 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
"The staff was very attentive and helpful. The restaurant and bar in the hotel was a delight."
Richard 3-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 highly rate The Inn at Chesapeake Bay Beach Club. From its handy amenities to its welcoming staff, everything about this 4-star hotel in Chester is designed to provide an exceptional vacation experience.
How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's filter tool, scoring an awesome deal on a 4-star hotel in Chester just got simpler. Start by entering your chosen arrival date and length of your escape. Then list the results by price and pick a property that best matches your budget and style.

  • Search for the lowest price from $457

What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveler experience and upmarket décor, 4-star hotels are a fabulous option for your Chester getaway. These kinds of stays generally feature lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to pamper with luxury perks and amenities. Round-the-clock concierge service, premium toiletries and world-class dining are typically included at these deluxe retreats.