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Find 4 Star Hotels in Chestertown, MD from AED 886

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Check availability on Chestertown 4 Star Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

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, (870)
"Beautiful location, big rooms "
The price is AED 777
AED 886 total
includes taxes & fees
2 Nov - 3 Nov
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, (421)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is AED 716
AED 888 total
includes taxes & fees
2 Nov - 3 Nov
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 1,366 per night from Oct 19 to Oct 20
AED 1,366
AED 1,757 total
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (1,000 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

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

See all hotels in Chestertown
Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

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 1,757

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.

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