Photo by Patricia Knorr

Search Houseboats in Chester

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

Waterfront Oasis of Annapolis FIRSTIE
This is FIRSTIE! A truly unique houseboat experience.

Waterfront Oasis of Annapolis FIRSTIE

10.0 out of 10, Exceptional, (18)
"We had a great time at this vrbo! Loved the roof"
Waterfront Oasis of Annapolis FIRSTIE
Cass-Away Luxury Houseboat
Miscellaneous

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (89)
"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
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-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (20)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
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, (3)
"Enjoyed the stay"
The price is AED 767
AED 1,677 total
includes taxes & fees
6 Jan - 7 January 2025
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
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
6.0 out of 10, (2)
"My husband and I had never before stayed in a "floating condo", and we loved it! The yacht was comfortable, impeccably decorated, and equipped with every single thing necessary for our 3-night stay...Of course, the glorious mid-October weather and beautiful Chesapeake Bay Kent Island marina view elevated the experience to a Wow, Wow, WOW! "
Floating 2 bed 2 bath condo stunning views of the bay
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Marina

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

The price is AED 8,815
AED 12,390 total
includes taxes & fees
24 Dec - 25 Dec
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Six bedroom 2020 Fountaine Pajot catamaran
Room

Six bedroom 2020 Fountaine Pajot catamaran

Six bedroom 2020 Fountaine Pajot catamaran
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 Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Ready to Relax and Enjoy the Water and Sunset Views?

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

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

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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 Chester with Expedia?
Reserving a houseboat in Chester is as easy as deciding on your travel dates and picking an option that satisfies your needs. Seeking a floating retreat that’s affordable or upmarket, or a stay that also comes with free WiFi? Use Expedia’s search filters to narrow your results even further and find your perfect match.
How can I find cheap houseboats in Chester?
Expedia’s filters make it a breeze to find cheap houseboats in Chester. Tailor your search results by your budget and preferred star rating — lower-rated houseboats are friendlier on the finances. You can also sign up for Expedia Rewards to land a discount on your floating home away from home.