Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from SAR 364

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Check availability on Chester 4 Star Hotels

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

Our top choices for Chester 4-star hotels

Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1008)
"Great area and it was a perfect hotel for our trip. "
The price is SAR 603
SAR 687 total
includes taxes & fees
2 Sep - 3 Sep
Graduate by Hilton Annapolis
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1000)
"Great place! "
The price is SAR 709
SAR 808 total
includes taxes & fees
22 Aug - 23 Aug
The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (856)
" Very clean, spacious room, friendly staff"
The price is SAR 890
SAR 1,014 total
includes taxes & fees
1 Sep - 2 Sep
Annapolis Waterfront Hotel, Autograph Collection
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1009)
"Easy access, friendly staff, clean as well"
The price is SAR 364
SAR 415 total
includes taxes & fees
31 Aug - 1 Sep
DoubleTree by Hilton Hotel Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (411)
"Great location and amenities"
The price is SAR 844
SAR 1,033 total
includes taxes & fees
25 Aug - 26 Aug
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (34)
"The facility designed was out standing and the staff was very good. "
The price is SAR 1,550
SAR 1,705 total
includes taxes & fees
24 Aug - 25 Aug
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 SAR 2,081 per night from Aug 24 to Aug 25
SAR 2,081
SAR 2,518 total
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (359 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
"Nice hotel, convenient location with easy parking. "
Jessica 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

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 favorite 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 SAR 1,263

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.