Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from AED 340

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Check availability on Chester 4 Star Hotels

Tonight
3 Apr - 4 Apr
Tomorrow
4 Apr - 5 Apr
This weekend
4 Apr - 6 Apr
Next weekend
11 Apr - 13 Apr

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

The Westin Annapolis
City view from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Always love our Westin Annapolis stay - can’t wait to see it post construction "
The price is AED 547
AED 624 total
includes taxes & fees
6 Apr - 7 Apr
The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, 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, (808)
"Good "
The price is AED 702
AED 801 total
includes taxes & fees
20 Apr - 21 Apr
Annapolis Waterfront Hotel, Autograph Collection
DoubleTree by Hilton Hotel Annapolis
Lobby

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1004)
"Hotel is close to everything, mall, food, shopping"
The price is AED 340
AED 388 total
includes taxes & fees
20 Apr - 21 Apr
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1003)
"I loved my stay here!"
The price is AED 559
AED 637 total
includes taxes & fees
14 Apr - 15 Apr
Graduate by Hilton 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, (376)
"Great spot!"
The price is AED 643
AED 807 total
includes taxes & fees
8 Apr - 9 Apr
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, (30)
"Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!"
The price is AED 1,418
AED 1,560 total
includes taxes & fees
17 Apr - 18 Apr
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 1,769 per night from Apr 7 to Apr 8
AED 1,769
AED 2,140 total
includes taxes & fees
7 Apr - 8 Apr
9.4/10 Exceptional! (337 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

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 937

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.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream hotel in Chester is as simple as entering your travel dates and destination, and selecting our “All inclusive” filter. Stay and play where just about everything is already taken care of like your room, meals and activities, or opt for a standard 4-star resort in or around this sought-after destination.
What are the top 4-star hotels in downtown Chester?
Enjoy the sights with ease when you check in to The Inn at Chesapeake Bay Beach Club. About 5 kilometers west from downtown Chester, this 4-star hotel offers the perfect spot to make the most of this buzzing city with the added convenience of Frette Italian sheets and a cafe.