Photo by Julie Miller

Chestertown cabins

We found 45 cabins — 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, 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 cabin rental in Chestertown?
Spacious or compact, upmarket or simple — Vrbo has cabin rentals for every budget. To find a getaway that suits yours, take advantage of our price filter. You can fine-tune your search results by the maximum total or nightly price. The cost will vary based on the type of property you want, but the one thing that remains constant? The thrill that comes with spending your break in one of our Chestertown cabin rentals.
Can I book a cabin with a hot tub in Chestertown?
Book a cabin rental with a hot tub and take your Chestertown getaway to a blissful level of relaxation. Just click on "Hot tub" under our features and amenities filter to discover cabins with this premium perk. Sinking into the bubbles after a busy day will be among the highlights of your trip.