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Find 4 Star Hotels in Chestertown, MD from SAR 807

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Check availability on Chestertown 4 Star Hotels

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, (826)
"Front desk staff was very friendly and helpful."
The price is SAR 875
SAR 997 total
includes taxes & fees
21 Jul - 22 Jul
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, (391)
"Beautiful place, quiet and clean. "
The price is SAR 807
SAR 991 total
includes taxes & fees
13 Jul - 14 Jul
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 SAR 1,295 per night from Jul 21 to Jul 22
SAR 1,295
SAR 1,676 total
21 Jul - 22 Jul
includes taxes & fees
9.4/10 Exceptional! (1,001 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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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 SAR 1,295

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 vacation bliss in Chestertown is as easy as entering your travel details and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodations, meals and activities, or choose a standard 4-star resort in or around this top destination.