Photo by Assya A

Chestertown cabins

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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 cabin rental in Chestertown?
Small or sprawling, basic or fancy — Vrbo has cabin rentals for every budget. To find an escape that matches yours, use our price filter. You can fine-tune your search results by the maximum total or nightly price. The cost will vary based on the sort of property you're after, but the one thing that stays the same? The thrill that comes with leaving the everyday behind in one of our Chestertown cabin rentals.
Where can I rent a Chestertown cabin rental with great views?
Our Chestertown cabin rentals let you immerse yourself in the great outdoors from the comfort of your hideaway. To book one that comes with great views, use our convenient filters. Select "Guest rating" to find cabins other guests recommend, or filter your search by "Location."
Does Chestertown have any lake cabins?
Lapping water, gorgeous sunsets and recreational opportunities are just the start of things to look forward to when you book a lake cabin rental in Chestertown. Search for cabins around well-known expanses like Cow Pond. Whether the plan is to explore nature trails or simply chill out, you can do as much or as little as you wish.
Can I book a luxury cabin in Chestertown?
Experience a taste of the good life on your trip to Chestertown by selecting a luxury cabin rental. These high-end properties will spoil you with top-of-the-line amenities such as pools and hot tubs. Use our handy filters to look for cabins that are highly rated by guests and get the outdoor experience without having to rough it!
Can I book a cabin with a hot tub in Chestertown?
Sink into a state of bliss when you step into the hot tub of your cabin rental. It's quick and easy to find stays in Chestertown with this luxury amenity by selecting "Hot tub" in the search filters. With the soothing bubbles waiting for you, you'll be happy to return to your cosy cabin escape after spending the day in nature.
What are the top things to do in Chestertown?
It's no surprise why many families love Chestertown, with top attractions like Rock Hall Harbour, Betterton Beach and Rolphs Wharf Marina to explore. Check out this destination's best sights together and then return to the comforts of your cabin rental.
Why should I book my cabin rental with Vrbo?
When you choose a Vrbo cabin rental, the only people you have to share your space with are the people you bring with you. It'll just be you, your family and the entire place for your exclusive use. Our flexible cancellation policies also mean you can book your cabin with confidence if you have to change your plans.