Photo by Assya A

Chestertown cottages

We found 4 cottages — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a cottage rental in Chestertown?
A number of factors will influence the price of a cottage rental in Chestertown, such as the size of the property and when and how long you're staying. All you have to do is enter your travel dates and preferences to find a cottage that matches your style and budget.
Where can I rent a Chestertown holiday cottage with great views?
Providing more than just a place to hang your hat, our cottage rentals promise an unforgettable retreat surrounded by the kind of views you love. Whether that's nature, cityscapes or a blend of both, use our filter tools to narrow your search for your perfect holiday. Find cottages in Chestertown that have decks or balconies so you can take in the beautiful scenery.
Does Chestertown have any lakeside cottages?
For a welcome change of scenery, it's tough to beat our lakeside cottage rentals. Try our "Location" filter tool and then click on "Lake" to see if you can find any cosy stays that'll place you near the water in Chestertown. Spend your days being adventurous or simply enjoy watching magnificent sunrises and sunsets glittering off the lake.
What are the top things to do in Chestertown?
It's no surprise why families love Chestertown, with cool attractions like Rock Hall Harbour, Betterton Beach and Rolphs Wharf Marina to explore. Uncover this destination's wonders together and then return to the comforts of your cottage rental.
Why should I book my holiday cottage with Vrbo?
Vrbo offers customer support from the instant you book until the end of your trip, so every aspect of your stay is stress-free. Plus we think our cottage rentals are something pretty special — think amenity-packed stays ideal for families and rustic options that are perfect for a romantic break. Book with Vrbo and you can also take advantage of flexible cancellation policies and other benefits like deposit and payment protection.