Photo by Assya A

Chestertown rentals with pool

We found 14 rentals with pool — 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 holiday rentals with a pool in Chestertown?
Stay in one of our 14 holiday rentals with a pool in Chestertown and get ready for fun and games in the water. Pomona, Edesville and Price are among the city's best areas to stay.
How much does it cost to stay in a holiday rental with a pool in Chestertown?
Plunge pool or rooftop pool, one bedroom or six, busy or quiet season — how much you'll pay for your Chestertown stay is influenced by all sorts of variables. But the one thing that stays the same? Our holiday rentals with a pool are where fun family memories are made. To find a getaway that suits your budget, narrow your search results by your maximum price. You can also use our "Discounts" filter to find properties that offer savings on longer stays.
What holiday rentals with a pool in Chestertown have nice views?
Whether it's a morning swim or an evening dip, a holiday rental with a pool offers endless hours of fun by the water. Toss in some outstanding views and you'll never want your adventure to end. Use our filters to personalise your search for a Chestertown holiday home that has the amenities you want and outlooks that'll leave a lasting impression.
Are there holiday rentals with a private pool in Chestertown?
From poolside get-togethers to solo soaks, a holiday rental with a private pool gives you plenty of possibilities for relaxation and fun. If you're travelling to Chestertown, use our "Private pool" filter to search for stays that come with this exclusive amenity.
What are the top things to do in Chestertown?
Rock Hall Harbour, Betterton Beach and Rolphs Wharf Marina are places to add to your must-visit list while staying at a holiday home rental with a pool in Chestertown. The only thing that beats exploring this city's leading attractions? Unwinding poolside with the fam after an action-packed day of activities and tours.
Why should I book my holiday rental with a pool with Bookabach?
When you book a holiday rental with a pool with Bookabach, you'll get more than the basic hotel experience — think a private pad with a place to chill out by the water. You're also covered by our Book with Confidence Guarantee. This means we're here to ensure everything goes off without a hitch throughout your entire getaway. Have an unexpected change to the itinerary? Check out our cancellation policies to see if you are eligible for a complete refund.