Photo by Assya A

Search Houseboats in Chestertown

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 Jum. I - 18 Jum. I
In two weeks
23 Jum. I - 25 Jum. I
In one month
6 Jum. II - 8 Jum. II
In two months
4 Raj. - 6 Raj.

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

Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"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-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (26)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel 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
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

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

9.6 out of 10, Exceptional, (24)
"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
Property grounds

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

9.8 out of 10, Exceptional, (9)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
The price is SAR 945
SAR 2,120 total
includes taxes & fees
13 May - 14 May
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Cass-Away Luxury Houseboat
Smart TV

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (92)
"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
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Terrace/patio

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 SAR 862
SAR 1,798 total
includes taxes & fees
12 May - 13 May
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Condo Houseboat
Miscellaneous

Condo Houseboat

10.0 out of 10, Exceptional, (2)
"Comfortable with gorgeous views"
Condo Houseboat
Houseboat Scorpius by SleepAfloat
Family House, 2 Bedrooms, Kitchen, Harbor View | Private kitchen | Fridge, microwave, stovetop, coffee/tea maker

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.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

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

10.0 out of 10, Exceptional, (215)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is SAR 656
SAR 1,010 total
includes taxes & fees
18 May - 19 May
BAYSIDE BUNGALOW
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.