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Search Houseboats in Chestertown

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Houseboats in Chestertown

40' Bristol sailboat with spectacular views
Interior

40' Bristol sailboat with spectacular views

2.0 star property
The price is AED 1,102
AED 1,577 total
includes taxes & fees
6 Oct - 7 Oct
40' Bristol sailboat with spectacular views
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Marina

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

The price is AED 675
AED 1,665 total
includes taxes & fees
8 Oct - 9 Oct
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Terrace/patio

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
The price is AED 579
AED 1,463 total
includes taxes & fees
20 Oct - 21 Oct
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Exterior

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

9.8 out of 10, Exceptional, (10)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
The price is AED 964
AED 2,229 total
includes taxes & fees
6 Oct - 7 Oct
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
3-bedroom boat in amazing Annapolis with AC
Marina

3-bedroom boat in amazing Annapolis with AC

The price is AED 3,967
AED 5,527 total
includes taxes & fees
8 Oct - 9 Oct
3-bedroom boat in amazing Annapolis with AC
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 Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful hotel in the heart of Annapolis. Lots of charm "
Sara 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

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.
How can I find cheap houseboats in Chestertown?
Expedia's filters make it a snap to find cheap houseboats in Chestertown. Tailor your search results by your budget and desired star rating — lower-rated houseboats are usually less expensive. You can also sign up to One Key™ for free to unlock more discounts on your floating escape.