Chestertown Houseboats

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Houseboats in Chestertown

Cass-Away Luxury Houseboat

Located in Grasonville, this houseboat is on the waterfront, a 2-minute drive from Chesapeake Exploration Center and 8 minutes from Queenstown Premium Outlets.

Chesapeake Houseboat Getaway on Kent Island, Maryland

With a stay at this houseboat in Stevensville, you'll be within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.

Luxe Houseboat with Epic 360 Views

$289

per night

Apr 28 - Apr 29

With a stay at this houseboat, you'll be centrally located in Baltimore, a 4-minute drive from Johns Hopkins Hospital and 6 minutes from National Aquarium in Baltimore.

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

$210

per night

Apr 22 - Apr 23

When you stay at this houseboat in Arnold, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay Bridge and U.S. Naval Academy.

Condo Houseboat

When you stay at this houseboat in Annapolis, you'll be on the waterfront, within a 15-minute walk of U.S. Naval Academy and Annapolis Maritime Museum.

Houseboat Scorpius by SleepAfloat

2001 Aliceanna St., Baltimore, MD

With a stay at this houseboat in Baltimore (Fells Point), you'll be within a 5-minute drive of National Aquarium in Baltimore and Baltimore Convention Center.

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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.