Search Houseboats in Shady Side

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Compare 9 Houseboats in Shady Side with updated reviews, rates, and availability.

Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Cass-Away Luxury Houseboat
Miscellaneous

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (89)
"This is a great getaway place!! Very nice on the water. Lots to do in the area! Tiki Bars restaurants must stop while traveling or vacationing!"
Cass-Away Luxury Houseboat
Chesapeake Houseboat Getaway on Kent Island, Maryland
Exterior

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

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

10.0 out of 10, Exceptional, (4)
"Enjoyed the stay"
The price is AED 575
AED 1,434 total
includes taxes & fees
13 Jan - 14 Jan
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Condo Houseboat
Private kitchen

Condo Houseboat

10.0 out of 10, Exceptional, (2)
"Comfortable with gorgeous views"
Condo Houseboat
Floating 2 bed 2 bath condo stunning views of the bay
Marina

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
7.4 out of 10, Good, (3)
"My husband and I had never before stayed in a "floating condo", and we loved it! The yacht was comfortable, impeccably decorated, and equipped with every single thing necessary for our 3-night stay...Of course, the glorious mid-October weather and beautiful Chesapeake Bay Kent Island marina view elevated the experience to a Wow, Wow, WOW! "
Floating 2 bed 2 bath condo stunning views of the bay
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Marina

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

The price is AED 8,815
AED 12,616 total
includes taxes & fees
12 Jan - 13 Jan
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Six bedroom 2020 Fountaine Pajot catamaran
Room

Six bedroom 2020 Fountaine Pajot catamaran

Six bedroom 2020 Fountaine Pajot catamaran
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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Other property types in Shady Side

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.

Frequently asked questions

Why book your houseboat in Shady Side with Expedia?
Expedia will help you find houseboats in Shady Side — from cute and cozy options to floating palaces! If you have a budget in mind, select how much you’d like to spend and the preferred star rating of your vessel. We’ll help you find the right stay whatever your bank balance or plans.
How can I find cheap houseboats in Shady Side?
Expedia’s filters make it a snap to find cheap houseboats in Shady Side. Tailor your search results by your budget and preferred star rating — lower-rated houseboats won’t hit your bank balance as hard. You can also join Expedia Rewards for free to reel in special deals on your floating stay.