Photo by Assya A

Search Chestertown Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Chestertown

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is S$605
includes taxes & fees
17 Aug - 18 Aug
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

The Inn at Henderson's Wharf, Ascend Hotel Collection

The Inn at Henderson's Wharf, Ascend Hotel Collection

10/10 Excellent
"I loved room 121. It was a beautiful architecture and view. Very quiet and comfortable. The hosts were super friendly, offered us a check in drink, but I was almost late for my BYOB Urban Pirate cruise, so I had to decline. There is a bakery right around the corner, and lots of great food and shopping to walk to. I was there to enjoy the old town walks and shops and I sure did!"
Susan 2-night trip
Posted 2 days ago
The Inn at Henderson's Wharf, Ascend Hotel Collection

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that travelling should be stress-free, so if you're chasing cottages in Chestertown at a competitive rate, Expedia delivers. Save cash and select a wallet-friendly option surrounded by nature, or book an upmarket cottage to pamper your favourite people.
How can I find cheap cottages in Chestertown?
The simplest way to track down cheap cottages in Chestertown is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.
What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.