A coastal town with a marina, a bridge, and a highway.

Search Houseboats in Chester from CA $366

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chester houseboats

A small, single-story structure with a sloped roof, a balcony, and a covered outdoor area.

1. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is CA $127
CA $366 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

2. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis
Arnold
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveller
The price is CA $258
CA $581 total
includes taxes & fees
Nov 15 - Nov 16
Houseboat Suite for Two near Annapolis
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

3. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is CA $261
CA $617 total
includes taxes & fees
Nov 8 - Nov 9
Bay Sunsets for Two • Rooftop Fire Pit
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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Top Chester Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Beautiful property. Brand new and very well done. Incredibly nice staff."
gary 3-night trip
Posted 18 hours ago
The Inn at Chesapeake Bay Beach Club

Find out more about Chester

Chester Houseboats information

Number of reviews
68
Accommodation
10 Houseboats
Lowest Price
CA $366
Highest Price
CA $617

Frequently asked questions

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