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Search Houseboats in Chestertown

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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

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

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (343)
"I stayed here one night and got a stripper pregnant. 10/10 will book again. "
The price is AED 251
AED 279 total
includes taxes & fees
13 Apr - 14 Apr
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (754)
"Check-in was quick & easy. The gentleman at the desk was wonderfully pleasant and very welcoming. Our room was clean and spacious. Beds were clean and comfortable. "
The price is AED 376
AED 417 total
includes taxes & fees
20 Apr - 21 Apr
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (46)
"Generally okay, Clean but property could use some upgrade"
The price is AED 397
AED 440 total
includes taxes & fees
20 Apr - 21 Apr
The Lodge at Great Oak Landing
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (169)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AED 233
AED 259 total
includes taxes & fees
7 Apr - 8 Apr
Driftwood Inn
Blue Heron Farm Waterfront Chalet
Miscellaneous

Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet
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 Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

9.8 out of 10, Exceptional, (22)
"Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

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

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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 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?
If you’re seeking fabulous deals on houseboats in Chestertown, you’ll want to implement several filters into your search. Start by sorting your results by price so that the cheapest options appear at the top. Then, adjust your filters to suit your budget. Expedia can help you find your dream floating getaway whatever your plans or budget.