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Search Houseboats in Chestertown

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

Cass-Away Luxury Houseboat
Miscellaneous

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
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
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Marina

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

9.8 out of 10, Exceptional, (9)
"I took my three daughters on a girls weekend trip and wanted to do something different… This houseboat was perfect! Not only did it have every amenity we could need, but the rooftop was spectacular, the home was modern and efficient, and Brian was an amazing host!"
The price is AED 1,400
AED 2,690 total
includes taxes & fees
2 Dec - 3 Dec
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (17)
"Very relaxing"
Cass-N-Reel Luxury Houseboat
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, (3)
"Enjoyed the stay"
The price is AED 744
AED 1,651 total
includes taxes & fees
1 Dec - 2 Dec
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
6.0 out of 10, (2)
"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
Houseboat Scorpius by SleepAfloat
Exterior

Houseboat Scorpius by SleepAfloat

2.5 star property
10.0 out of 10, Exceptional, (1)
"unreal! In the heart of Fells Point section - great restaurants, bars and so easy to get to the convention center. I had cocktails on the top deck every night when I came back from my meetings. I saved $300 a night staying here with $12 in Uber every day - even took the water taxi just to add a bit of cool to the trip!"
Houseboat Scorpius by SleepAfloat
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 Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
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, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
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 Chestertown with Expedia?
Booking a houseboat in Chestertown is as easy as deciding on your travel dates and picking the option that meets your requirements. Seeking a floating retreat that’s luxurious or affordable, or a stay that also has a hot tub and free WiFi? Use Expedia’s search filters to narrow your results even further and find your dream fit.
How can I find cheap houseboats in Chestertown?
If you’re trying to find fantastic deals on houseboats in Chestertown, implement a few filters into your search. You can sort your results by price so that the cheapest options are displayed first. Then, change your filters to match your budget. Expedia can help you find your dream floating getaway whatever your plans or bank balance.