Photo by Assya A

Chestertown beach rentals

We found 7 beach rentals — 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

Are there any beach holiday rentals in Chestertown?
Pick one of our 7 beach holiday rentals in Chestertown and you'll have a perfect base for your next escape to the coast. Pomona, Edesville and Price are among this city's most sought-after neighbourhoods.
How much does it cost to stay in a beach holiday rental in Chestertown?
The size of your beach holiday rental and the number of bedrooms will determine how much you have to pay. Another factor that impacts the price is the types of amenities it has, like a pool or hot tub. If you're planning to stick around a while, use our "Discounts" filter to look for properties in Chestertown that offer long-stay deals. Just decide when you want to spend your days strolling by the shoreline and let Bookabach look after the rest.
Where can I book a Chestertown beach holiday rental with great views?
Bookabach's filters will help you find a Chestertown beach holiday rental with a view. After selecting your trip dates, click on "Highly rated for location" under "Property reviews." You can also search via the "Location" filter. Your own private space with awesome views and a refreshing sea breeze? A getaway doesn't get much better than this.
What are the top things to do in Chestertown?
After you've secured your beach holiday rental, start filling your agenda with family-friendly sights like Rock Hall Harbour and Betterton Beach. If you can make some time between all those relaxing shoreline strolls, visit Rolphs Wharf Marina too.
Why should I book my beach holiday rental with Bookabach?
With our handy filters, excellent customer support and flexible cancellation policies, planning your coastal getaway is now more effortless than ever. Experience the joy of having the whole property to yourselves, allowing you to savour the gorgeous views and salty sea air in privacy. Book your beach holiday rental with Bookabach and we'll guarantee a hassle-free trip from start to finish.