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Search Houseboats in Chestertown

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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

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

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.

9.4 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.
Cass-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (23)
"The perfect little get away!"
The price is AED 367
AED 969 total
includes taxes & fees
3 Apr - 4 Apr
Cass-N-Reel Luxury Houseboat
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (22)
"We had an amazing time "
Chesapeake Houseboat Getaway on Kent Island, Maryland
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
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)
"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 960
AED 2,109 total
includes taxes & fees
25 Mar - 26 Mar
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, (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
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)
"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 644
AED 1,526 total
includes taxes & fees
24 Mar - 25 Mar
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.
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Other property types in Chestertown

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, (209)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (22)
"We had an amazing time "
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?
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.