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Search Houseboats in Chestertown

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

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

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

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 968
AED 2,147 total
includes taxes & fees
10 Mar - 11 Mar
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

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

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (89)
"We enjoyed our stay from the beginning to the end. Check in was smooth with great communication from the host. The interior of the houseboat looks better in person. It was spacious and clean with unforgettable views. The beds were comfortable and the sectional in the living area was very relaxing. What a great experience! Thanks for everything!"
Cass-Away Luxury Houseboat

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
7.4 out of 10, Good, (3)
"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "
Floating 2 bed 2 bath condo stunning views of the bay

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

10.0 out of 10, Exceptional, (4)
"The property was absolutely beautiful and clean. The property was tuck away in a very relaxing and reserved spot. The place was so peace and calming . I do suggest one thing if you go in the winter months please bring extra blankets and warm Pjs due to the boat house does tend to get chilling even with the heat on the max."
The price is AED 548
AED 1,392 total
includes taxes & fees
5 Mar - 6 Mar
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Condo Houseboat

10.0 out of 10, Exceptional, (2)
"Comfortable with gorgeous views"
Condo Houseboat

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

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is AED 360
AED 579 total
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown

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.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (256)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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?
With Expedia, it’s a cinch to find houseboats in Chestertown — from small, rustic options to luxurious floating palaces! If you have a budget, select how much you’re willing to spend and your preferred star rating. We’ll help you find the right stay whatever your style of travel or plans.
How can I find cheap houseboats in Chestertown?
If you’re seeking fabulous deals on houseboats in Chestertown, you’ll want to implement several filters into your search. Start by sorting your results by price so that the cheapest options appear at the top. Then, adjust your filters to suit your budget. Expedia can help you find your dream floating getaway whatever your plans or budget.