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Compare 85 Apartments in Chestertown with updated reviews, rates, and availability.

Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (20)

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (29)

Bay View Studio Apartment
Bay View Studio Apartment
10.0 out of 10, Exceptional, (42)

Cozy 1st Floor King George one bedroom apartment right across from USNA
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (29)

Carriage House Hideaway in Middle of Chestertown
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, (86)

Historic Downtown Garden Oasis with Private Patio
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (25)

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (34)

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (45)
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.
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Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (22)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Holiday Inn Express White Marsh by IHG
5/5 Excellent
"Very clean and comfortable and breakfast and 24 hr coffee bar were excellent"
A verified traveler stayed at Holiday Inn Express White Marsh by IHG
Posted 3 days ago
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