Chestertown apartments

We found 10 apartments — enter your dates for availability

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    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 an apartment holiday rental in Chestertown?
Prices vary depending on the time of year, length of stay and specific location, so enter your holiday details to find out what's available. Whatever your budget or plans, Stayz has apartment and condo holiday rentals in Chestertown suited to guests of all types.
Where can I rent a Chestertown holiday apartment with great views?
The only thing better than a great holiday condo rental is one that offers a view. We've got options in Chestertown that boast fantastic vistas just a glance from your window. Use our filters to fine-tune your search for getaways located in picturesque areas or with specific views. What comes next? Relax and enjoy the outlook.
Does Chestertown have any weekend apartment rentals?
When you're craving a spur-of-the-moment escape, check out our holiday condo rentals in Chestertown that are perfect for a weekend retreat. Just enter your desired travel dates to see what's available. Can't find an apartment holiday rental that fits your needs? Stay flexible with your plans and try searching on other dates.
Can I book a luxury apartment in Chestertown?
Boasting deluxe perks like hot tubs and swimming pools, our luxury apartment holiday rentals in Chestertown will take your getaway to a whole new level. They generally come with stylish furniture, modern appliances and plenty more. If you want to really kick back and relax, search for holiday condo rentals that come with hotel-like services such as housekeeping.
What are the top things to do in Chestertown?
Rock Hall Harbour, Betterton Beach and Rolphs Wharf Marina are terrific attractions that'll keep the whole crew occupied in Chestertown. There's nothing like travel to get everyone together, so check out our apartment holiday rentals in this exciting destination.
Why should I book my apartment holiday rental with Stayz?
Book your apartment holiday rental with Stayz and experience more privacy and space compared to standard hotel accommodation. These types of stays promise that home-away-from-home ambience. One of the biggest advantages? You'll never have to share your space, whether you spend your break in an apartment or something a little swankier, like an estate or a villa.