Chestertown Houseboats

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Houseboats in Chestertown

Cass-N-Reel Luxury Houseboat

Grasonville MD

Located in Grasonville, this houseboat is a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island Dog Park.

Floating 2 bed 2 bath condo stunning views of the bay

Stevensville MD

When you a stay at this houseboat in Stevensville, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Baltimore MD

$460 nightly

$537 total

Jan 27 - Jan 28

Total with taxes and fees

With a stay at this houseboat, you'll be centrally located in Baltimore, a 5-minute drive from Johns Hopkins Hospital and 6 minutes from National Aquarium in Baltimore.

Cass-Away Luxury Houseboat

Grasonville MD

Located in Grasonville, this houseboat is on the waterfront, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island Dog Park.

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville MD

When you a stay at this houseboat in Stevensville, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Havre de Grace MD

With a stay at this houseboat in Havre De Grace, you'll be a 3-minute walk from Harford Memorial Hospital and 7 minutes by foot from Millard Tydings Memorial Park.

Kitchen

Washer

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

Arnold MD

$320 nightly

$365 total

Jan 27 - Jan 28

Total with taxes and fees

With a stay at this houseboat in Arnold, you'll be on the waterfront, within a 15-minute drive of U.S. Naval Academy and Severna Park Golf Center.

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena MD

$374 nightly

$426 total

Jan 28 - Jan 29

Total with taxes and fees

When you a stay at this houseboat in Pasadena, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Lovin’ Life !

Essex MD

$214 nightly

$247 total

Jan 25 - Jan 26

Total with taxes and fees

With a stay at this houseboat in Essex, you'll be within a 10-minute drive of Essex Marina and Wildwood Beach Land Trust.

40' Bristol sailboat with spectacular views

Stevensville MD

With a stay at this houseboat in Stevensville, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.

3-bedroom boat in amazing Annapolis with AC

Annapolis MD

With a stay at this houseboat in Annapolis (Historic District), you'll be within a 10-minute walk of U.S. Naval Academy and Annapolis Harbor.

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.