Photo by Assya A

Search Houseboats in Chestertown

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 9 Houseboats in Chestertown 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
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 SAR 965
SAR 2,160 total
includes taxes & fees
24 Feb - 25 Feb
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
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
Cass-Away Luxury Houseboat
Miscellaneous

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
Marina

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

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 SAR 571
SAR 1,456 total
includes taxes & fees
23 Feb - 24 Feb
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
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

'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is SAR 330
SAR 762 total
includes taxes & fees
25 Feb - 26 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
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
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
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.