Chestertown Houseboats

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Houseboats in Chestertown

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

Cass-Away Luxury Houseboat

Grasonville MD

$285 nightly

$315 total

Sep 25 - Sep 26

Total with taxes and fees

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

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena MD

$375 nightly

$427 total

Sep 3 - Sep 4

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

$487 nightly

$566 total

Aug 27 - Aug 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 7 minutes from Baltimore Convention Center.

Pool

Kitchen

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

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 10-minute walk of Chesapeake Bay and Harford Memorial Hospital.

Kitchen

Washer

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

Arnold MD

$320 nightly

$365 total

Aug 26 - Aug 27

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 Sandy Point State Park and Chesapeake Bay.

Kitchen

Free WiFi

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

Lovin’ Life !

Essex MD

$232 nightly

$268 total

Sep 7 - Sep 8

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

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.

Pet friendly

Air conditioning

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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.