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Chestertown house rentals

We found 48 house 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 holiday home rentals in Chestertown?
Pick from 48 holiday home rentals in Chestertown that offer more value, privacy, amenities and space than a standard hotel room. Browse houses in some of the more popular areas such as Pomona, Edesville and Price.
How much does it cost to stay in a holiday rental house in Chestertown?
Whether you're searching for a budget-friendly getaway or a lavish retreat, we offer a variety of holiday home rentals in Chestertown for you to choose from. Use our filter tools to narrow down your search and find the ideal stay for you and your guests.
Where can I rent a Chestertown holiday house with great views?
When looking for your holiday home rental in Chestertown, take advantage of our "Location" filter. This will help you narrow down the types of areas you want to stay in, whether that's near nature or somewhere more central.
Does Chestertown have any weekend house rentals?
Some of our holiday houses can be rented just for the weekend, making them perfect for whirlwind getaways. Enter your desired travel dates to check out the availability. You may need to adjust the dates and be flexible with your plans to find the best holiday home rental in Chestertown.
Are there any pet-friendly house rentals in Chestertown?
Yes, you'll find six holiday home rentals that allow pets in Chestertown, so your furry companion won't miss out on the excitement! Use our filter tool to browse for pet-friendly houses that feature perks like dogs beds and free treats for them, and a bunch of cosy amenities for you.
What are the top things to do in Chestertown?
Get your Chestertown getaway off to an amazing start by heading to top-rated attractions like Rock Hall Harbour, Betterton Beach and Rolphs Wharf Marina. Stay in a Stayz holiday home rental with the family and then discover this destination's wonders together.
Why should I book my holiday rental house with Stayz?
Booking your holiday home rental with Stayz means you'll have the whole property to yourselves — your own private retreat, without any interruptions from others. Not only that, our easy payment and cancellation policies give you the freedom to amend your plans if you need to.