Chestertown Houseboats

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Houseboats in Chestertown

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

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

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

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Baltimore MD

$493 nightly

$573 total

Mar 15 - Mar 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 Oriole Park at Camden Yards.

Pool

Kitchen

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

Arnold MD

$320 nightly

$365 total

Mar 12 - Mar 13

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

$429 nightly

$489 total

Mar 19 - Mar 20

Total with taxes and fees

When you 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

$221 nightly

$255 total

Mar 12 - Mar 13

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.

Kitchen

Washer

40' Bristol sailboat with spectacular views

Stevensville MD

$409 nightly

$434 total

Mar 12 - Mar 13

Total with taxes and fees

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

Kitchen

Water view

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

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 Susan Campbell Park.

Don't see what you're looking for?

See all available properties in Chestertown

View all properties

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.