Chesapeake City houses

We found 80 houses — 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 Chesapeake City?
Consider one of our 80 holiday home rentals and start making plans for your Chesapeake City trip. Whether you want to be in Arundel, Williamsburg, Yorkshire or another popular neighbourhood, you'll find the ideal house on Bookabach.
How much does it cost to stay in a holiday rental house in Chesapeake City?
Explore a variety of holiday home rentals in Chesapeake City, where prices vary to match every preference. From wallet-friendly choices to upscale properties, we make it easy to compare places and find the perfect stay for your next adventure.
Where can I rent a Chesapeake City holiday house with great views?
Stay at a holiday home rental in Chesapeake City and you'll be getting out of bed to impressive vistas. Some of our most popular rental houses in this destination boast views of historic areas.
Does Chesapeake City have any weekend house rentals?
Browse our weekend rentals and start packing for an exciting few days away. Our top tips for booking the ideal house in Chesapeake City? Stay flexible when searching and change your dates until you find the holiday home rental that matches your needs.
Are there any pet-friendly house rentals in Chesapeake City?
With our useful filter tool, finding a pet-friendly holiday home rental in Chesapeake City is a cinch. Simply click on "Pets allowed" to look for houses that come with amenities to make your four-legged friend feel welcome, such as pet toys and spacious yards to run around in.
What are the top things to do in Chesapeake City?
Planning a memorable escape to Chesapeake City means finding cool things for all the family. Lums Pond State Park, Kirkwood Soccer Complex and Elk Neck State Park are just two of the options here. And Bookabach's holiday home rentals are a terrific base for your sightseeing pursuits.
Why should I book my holiday rental house with Bookabach?
When you select a Bookabach holiday home rental, the only people you have to share your space with are whoever you bring along. It'll just be you, family or friends and the whole property to yourselves. Our flexible cancellation policies also mean you can book your rental house with confidence should your plans change.