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Chestertown Houseboat Rentals

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Compare 6 Houseboats in Chestertown with updated reviews, rates, and availability.

Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, (5)
"Perched on the furthest point of the marina you will feel like you are safely in a nest - especially on the roof top deck. The views of water birds, ships, sailboats and kayaks will entertain and relax you for hours. Feeling hungry? The marina has three great choices all with lovely views too. A great place to relax and recharge. The wonderful memories far outweigh the money spent. So worth it!"
The price is $331
$666 total
includes taxes & fees
May 29 - May 30
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
View from property
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (11)
"We enjoyed the property and the proximity to bars/restaurants. We enjoyed the view from the back porch and it is a nice place to relax. We would definitely recommend staying and look forward to booking another stay in the future."
The price is $150
$330 total
includes taxes & fees
May 23 - May 24
Cass-N-Reel Luxury Houseboat
Property grounds
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, (9)
"Clean, great location. Had a very relaxing weekend that was greatly needed. There was plenty of things to see and do in the beautiful town. Had a small problem but the host took care of it immediately. He was great. Thank you for a wonderful time."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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Property grounds
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (1)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
The price is $254
$515 total
includes taxes & fees
May 30 - May 31
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Smart TV
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (80)
"Very much enjoyed the houseboat. Perfect location - within walking distance of all local attractions / restaurants. Sunset view on the deck is amazing! Hope to come back soon!"
The price is $150
$364 total
includes taxes & fees
May 19 - May 20
Cass-Away Luxury Houseboat
Property grounds
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, (7)
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
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
Don't see what you're looking for?
See all available properties in Chestertown
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.

Other property types in Chestertown

Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (51)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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.

Chestertown Houseboats information

Number of reviews
103
Accommodation
6 Houseboats
Lowest Price
$150
Highest Price
$331

Frequently asked questions

Why book your houseboat in Chestertown with Expedia?
Booking a houseboat in Chestertown is as easy as clicking on your travel dates and picking an option that suits your style. Looking for a floating retreat that’s luxurious or affordable, or a stay that also comes with free WiFi? Use Expedia’s search filters to narrow your results even further and find your ideal match.
How can I find cheap houseboats in Chestertown?
Expedia will help you track down the perfect cheap houseboat in Chestertown. Just enter your travel dates and destination and then use our filters to refine your search according to your budget and other needs. Following that, it’s anchors aweigh!
What is there to do in Chestertown near my houseboat?
The ultimate travel accessory is a well-planned schedule. Historical Society of Kent County Maryland is a terrific place to start your sightseeing in Chestertown.

Recent reviews of Chestertown hotels
Expedia verified reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

5/5 Excellent
Great Room
"The room was spotless. The front desk was helpful. The complementary breakfast was delicious. I would definitely stay there again. "
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 23 hours ago
Fairfield Inn & Suites by Marriott White Marsh