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Find 4 Star Hotels in Chestertown, MD from AED 790

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Check availability on Chestertown 4 Star Hotels

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

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

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, (841)
"Front desk staff was very friendly and helpful."
The price is AED 809
AED 922 total
includes taxes & fees
17 Aug - 18 Aug
Annapolis Waterfront Hotel, Autograph Collection
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, (402)
"Staff was very polite and friendly. "
The price is AED 790
AED 970 total
includes taxes & fees
20 Aug - 21 Aug
The Inn at Chesapeake Bay Beach Club
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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 Chestertown.
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

1715 Thames St., Baltimore, MD
The price is AED 1,161 per night from Aug 6 to Aug 7
AED 1,161
AED 1,515 total
6 Aug - 7 Aug
includes taxes & fees
9.4/10 Exceptional! (1,005 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 Chestertown

Quaint Chestertown awaits: its sports, university life, art, and more!

See all hotels in Chestertown
Somewhere over the rainbow... Terrific view on the plane back to the North.
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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"The hotel offers a breathtaking view of the water. The room was clean, spacious, and comfortable. I found the staff to be attentive, friendly, and knowledgeable. They provided information regarding great places to eat and things to do. There is a wonderful yacht cruise that departs directly behind the hotel. Annapolis Waterfront Hotel, Autograph Collection is a walkable distance from the downtown attractions, including the Annapolis Naval Academy. Enjoy!"
Rebecca 2-night trip
Posted 2 weeks ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chestertown?
To book a 4-star hotel in Chestertown that's within your budget, take advantage of Expedia's filters. Take a look at the availability during your getaway dates and use our pricing filter to set your limit. You can also list your results by the most wallet-friendly option first.

  • Search for the lowest price from AED 1,161

What's the difference between 5-star and 4-star hotels in Chestertown?
Offering a friendly traveler experience and upmarket décor, 4-star hotels are a terrific option for your Chestertown trip. These types of stays generally feature lots of handy amenities that make it easy to unpack and recharge — think complimentary bathrobes, pools and gyms. Or enjoy even more lavishness at a 5-star hotel designed to spoil you with high-end perks and amenities. Concierge assistance, complimentary toiletries and world-class dining are typically included at these plush retreats.
Does Chestertown have any 4-star all-inclusive resorts?
Finding your dream hotel in Chestertown is as easy as typing in your travel details and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, meals and activities, or go for a standard 4-star resort in or around this top destination.