Houseboats in Eastern Shore
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your current months are November, 2026 and December, 2026.

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Our top choices for Eastern Shore houseboats

A small, single-story structure with a sloped roof, a balcony, and a covered outdoor area.

A modern kitchen with a built-in microwave, a coffee maker, and a sink. There is a dining area with a table and chairs, and a large window offering a view of the water.

A neatly made bed with white linens, two bedside lamps, a bedside table with a lamp, and a folded towel on the bed.

A deck with a view of a marina, including boats and docks.

1. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Grasonville

10.0 out of 10, Exceptional, (54 reviews)

10/10

Exceptional

(54 reviews)

"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."

Yamilet

The price is AU$368

AU$368

includes taxes & fees

12 Nov - 13 Nov

Cass-N-Reel Luxury Houseboat

A waterfront house with a dock, a covered outdoor seating area, and a view of the water.

A beach with a wooden boardwalk, ocean view, and trees.

A marina with boats docked, a sunset over the water, and trees in the foreground.

A room with a TV, a plant, a wicker chair, a wooden table, and a view of boats through large windows.

2. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit

Pasadena

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"

Charles W.

The price is AU$669

AU$669

includes taxes & fees

15 Nov - 16 Nov

Bay Sunsets for Two • Rooftop Fire Pit

A wooden deck with outdoor seating and a view of the water.

A modern kitchen with stainless steel appliances, a flat-screen TV, and a view of a water body through a sliding glass door.

A modern, well-lit room with a kitchenette, a sofa, a dining table, and a view of a canal.

A marina with docked boats, a small building with a balcony, and a gazebo by the water.

3. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis

Arnold

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."

Anonymous traveller

The price is AU$584

AU$584

includes taxes & fees

15 Nov - 16 Nov

Houseboat Suite for Two near Annapolis

A laundry room with a view of a dock and water, a washing machine, and a potted plant.

A rooftop terrace with a glass-top table, a fire feature, and a sofa.

A dining area with a view of the water, a framed bird artwork, and a menu stand.

A compact living space with a dining area, kitchenette, and a view of the water.

4. 2BR, 2 Bath Houseboat • Canton Harbor

2BR, 2 Bath Houseboat • Canton Harbor

Baltimore

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Very clean and well appointed houseboat. Location of marina is in a wonderful part of town and walkable to restaurants and shops. We would definitely do this again."

Shawna T.

The price is AU$766

AU$766

includes taxes & fees

1 Dec - 2 Dec

2BR, 2 Bath Houseboat • Canton Harbor

A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

A compact kitchen with a 'WELCOME' sign, a microwave, and a woven basket.

A compact living space with a white sofa, a television, and fishing rods on the ceiling.

A compact kitchen with wooden cabinets, a stainless steel refrigerator, and a sink.

5. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Bear

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"

Justin M.

The price is AU$401

AU$401

includes taxes & fees

15 Nov - 16 Nov

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

A living room with a view of a marina, a sofa, a chair, a TV, and a plant.

A modern boat with a deck area featuring a seating arrangement and a small table, docked at a marina with other boats and buildings in the background.

A modern living room with a sofa, coffee table, and large windows overlooking a cityscape.

A modern kitchen with white cabinets, a large island with bar stools, a stainless steel sink, and a view of the city through large windows.

6. Skyline Rooftop Houseboat • Inner Harbor

Skyline Rooftop Houseboat • Inner Harbor

Baltimore

10.0 out of 10, Exceptional, (28 reviews)

10/10

Exceptional

(28 reviews)

"Great stay, fun way to experience the inner harbour"

Matthew M.

The price is AU$976

AU$976

includes taxes & fees

16 Nov - 17 Nov

Skyline Rooftop Houseboat • Inner Harbor

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.

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Learn more about Eastern Shore

Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savour fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

See all hotels in Eastern Shore

Frequently Asked Questions

What is there to do in Eastern Shore near my houseboat?

The best accessory to take on your Eastern Shore escape is a fabulous itinerary! Ocean City Beach, Seacrets Distilling Company and Trimpers Rides are among the leading sights if you're headed to Ocean City. Berlin is also home to wonderful attractions, such as Globe Theatre. Want to add to your to-do list? Pencil in a visit to Main Street Berlin and The Bay Club too.

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Graduate by Hilton Annapolis
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Museum of Eastern Shore Culture at Salisbury University
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Activities in Washington
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Search Houseboats in Eastern Shore

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Eastern Shore houseboats

1. Cass-N-Reel Luxury Houseboat

2. Bay Sunsets for Two • Rooftop Fire Pit

3. Houseboat Suite for Two near Annapolis

4. 2BR, 2 Bath Houseboat • Canton Harbor

5. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

6. Skyline Rooftop Houseboat • Inner Harbor

Learn more about Eastern Shore

Frequently Asked Questions

What is there to do in Eastern Shore near my houseboat?

Explore a world of travel with Expedia