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Find 4 Star Hotels in Chester, MD from AED 399

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Check availability on Chester 4 Star Hotels

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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, (1,020 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is AED 350
AED 399 total
includes taxes & fees
5 Jul - 6 Jul
DoubleTree by Hilton Hotel Annapolis
Premium bedding, down comforters, pillowtop 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, (939 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 AED 809
AED 922 total
includes taxes & fees
6 Jul - 7 Jul
Annapolis Waterfront Hotel, Autograph Collection
Lobby lounge

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,003 reviews)
"Good location, nice hotel"
United States
Jiyoung
The price is AED 621
AED 708 total
includes taxes & fees
5 Jul - 6 Jul
The Westin Annapolis
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,003 reviews)
"Very fine place"
United States
David
The price is AED 590
AED 673 total
includes taxes & fees
6 Jul - 7 Jul
Graduate by Hilton 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, (467 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 AED 829
AED 1,013 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 AED 1,616
AED 1,778 total
includes taxes & fees
1 Jul - 2 Jul
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 AED 2,446 per night from Jul 23 to Jul 24
AED 2,446
AED 2,691 total
23 Jul - 24 Jul
includes taxes & fees
9.6/10 Exceptional! (391 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
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Nice hotel with proximity to many restaurants and shopping. We were there for a quick stay and did not utilize the hotel’s amenities. We did not encounter any issues during our stay. Of note: the front desk staff made sure we got our famous DoubleTree Cookies (yummy) and the A/C in the room worked great!"
Christine 1-night trip
Posted 1 day 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?
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 AED 1,379

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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