Hillsmere Shores Houseboats

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Houseboats in Hillsmere Shores

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

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

Sailboat Experience in Annapolis

Parole MD

With a stay at this houseboat, you'll be centrally located in Annapolis, within a 10-minute drive of U.S. Naval Academy and Annapolis Bowl.

Kitchen

Pet friendly

Annapolis Boat Life - Overnight Stays

ANNAPOLIS MD

With a stay at this houseboat in Annapolis, you'll be on the beach, within a 10-minute drive of U.S. Naval Academy and Annapolis Bowl.

Kitchen

Air conditioning

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

Downtown Nights on the Water - Classic Cruiser Getaway

Annapolis MD

A stay at this houseboat places you in the heart of Annapolis, within a 10-minute walk of Annapolis Landing Marina and Annapolis Sailing School.

Kitchen

Pet friendly

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

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Edgewater MD

$2,753 nightly

$3,138 total

Dec 12 - Dec 13

Total with taxes and fees

With a stay at this houseboat in Edgewater, you'll be on the waterfront, within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.

Kitchen

Ocean 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

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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.