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 7 minutes from Island Dog Park.

Kitchen

Free WiFi

Fully Equipped Docked Houseboat at Log Pond Marina in 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

Chesapeake Houseboat Getaway on Kent Island, Maryland

Located in Stevensville, this houseboat is on the waterfront, within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.

Kitchen

Pet friendly

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

$540

includes taxes & fees

$468 per night

Dec 19 - Dec 20

With a stay at this houseboat, you'll be centrally located in Baltimore, a 4-minute drive from Johns Hopkins Hospital and 8 minutes from Baltimore Inner Harbor Marina.

Pool

Kitchen

Cass-N-Reel Luxury Houseboat

$296

includes taxes & fees

$279 per night

Jan 2 - Jan 3, 2025

Located in Grasonville, this houseboat is 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

$410

includes taxes & fees

$368 per night

Jan 5 - Jan 6, 2025

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

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.

Air conditioning

Floating 2 bed 2 bath condo stunning views of the bay

Located in Stevensville, this houseboat is within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.

Kitchen

Pet friendly

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.