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.

Kitchen

Free WiFi

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.

Kitchen

Pet friendly

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Baltimore MD

$481 nightly

$559 total

Dec 15 - Dec 16

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 8 minutes from Baltimore Inner Harbor Marina.

Pool

Kitchen

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.

Kitchen

Free WiFi

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.

Kitchen

Pet friendly

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

Dec 15 - Dec 16

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.

Kitchen

Free WiFi

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena MD

$370 nightly

$422 total

Dec 18 - Dec 19

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.

Kitchen

Free WiFi

Lovin’ Life !

Essex MD

$216 nightly

$250 total

Dec 11 - Dec 12

Total with taxes and fees

With a stay at this houseboat in Essex, you'll be within a 15-minute drive of Essex Marina and Chesapeake Bay.

Kitchen

Washer

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.

Kitchen

Water view

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.

Pet friendly

Air conditioning

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 Johns Hopkins Hospital and National Aquarium in Baltimore.

Kitchen

Pet friendly

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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.