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

Kitchen

Pet friendly

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

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

Arnold MD

$348 nightly

$396 total

Oct 22 - Oct 23

Total with taxes and fees

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

Kitchen

Free WiFi

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena MD

$436 nightly

$497 total

Nov 9 - Nov 10

Total with taxes and fees

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

Kitchen

Free WiFi

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Baltimore MD

$506 nightly

$589 total

Nov 9 - Nov 10

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

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 within a 15-minute drive of Chesapeake Bay and Ripken Stadium.

Kitchen

Washer

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville MD

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

Kitchen

Pet friendly

Lovin’ Life !

Essex MD

$229 nightly

$265 total

Oct 21 - Oct 22

Total with taxes and fees

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

Kitchen

Washer

The Captain - Floating 2 bed 2 bath condo stunning views of the bay

Stevensville MD

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

Pool

Kitchen

3-bedroom boat in amazing Annapolis with AC

Annapolis MD

With a stay at this houseboat in Annapolis (Historic District), you'll be a 3-minute walk from Annapolis City Dock and 9 minutes by foot from U.S. Naval Academy.

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.