Search Houseboats in Chestertown from CA $127

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Chestertown 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
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

2. 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 $309
CA $674 total
includes taxes & fees
Nov 16 - Nov 17
Bay Sunsets for Two • Rooftop Fire Pit
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

3. 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 laundry room with a view of a dock and water, a washing machine, and a potted plant.

4. 2BR, 2 Bath Houseboat • Canton Harbor

2BR, 2 Bath Houseboat • Canton Harbor
Baltimore
10.0 out of 10, Exceptional, (16 reviews)
"Very clean and well appointed houseboat. Location of marina is in a wonderful part of town and walkable to restaurants and shops. We would definitely do this again."
United States
Shawna T.
The price is CA $316
CA $740 total
includes taxes & fees
Dec 1 - Dec 2
2BR, 2 Bath Houseboat • Canton Harbor
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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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top reviews in Chestertown

A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Excellent

Bon service
Canada
Sébastien
Reviewed August 22, 2026
Comfort Inn & Suites Chestertown

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.

What is there to do in Chestertown near my houseboat?

Once you've unpacked your bags and settled in, head out and explore the amazing things Chestertown has on offer. Rolphs Wharf Marina is a popular attraction to add to your must-do list.

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