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

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

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

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

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

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

10.0 out of 10, Exceptional, (2)
"Comfortable with gorgeous views"
Condo Houseboat

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.

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

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!

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!

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

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

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