Photo by Sarah Chiricosta

Chesapeake house rentals

We found 3,391 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 Chesapeake?
Take your pick of 3,391 holiday home rentals in Chesapeake that have more privacy, space, amenities and value than the average hotel room. Browse houses in some of the more popular neighbourhoods such as South Norfolk, Greenbrier West and Deep Creek South.
How much does it cost to stay in a holiday rental house in Chesapeake?
Your dream holiday home rental in Chesapeake is waiting to be discovered, with prices varying from budget-friendly accommodation to more exclusive options. Enter your travel dates to filter your search, making sure you find the right place for your getaway.
When is the best time to rent a holiday house in Chesapeake?
August is when most guests stay in a holiday home rental in Chesapeake, which is located in Chesapeake City County. On average, temperatures range from 23ºC to 30ºC during this time of year.
Where can I rent a Chesapeake holiday house with great views?
Go ahead and book one of our Chesapeake houses with views of historic areas. The one thing better than spending your escape in a Stayz holiday home rental? Kicking back in a property with gorgeous scenery right outside your window.
Does Chesapeake have any weekend house rentals?
You'll discover a range of wonderful houses that are available for weekend rental. Simply key in your travel dates and look forward to an impromptu few days of fun. If you can't find the ideal holiday home rental in Chesapeake straight away, just play around with your dates and search again.
Are there any pet-friendly house rentals in Chesapeake?
If you'd love to experience Chesapeake with your furry friend at your side, use our handy filter tool to browse pet-friendly houses. Check the "Pets allowed" box to find a holiday home rental with welcome touches like complimentary treats and dog bedding. After all, when the family goes away, the pets should share in the adventure!
What are the top things to do in Chesapeake?
Planning an unforgettable escape to Chesapeake means finding fun things for all ages to enjoy. Norfolk Botanical Garden, Nauticus National Maritime Centre and Chrysler Museum of Art are just the start of the options here. And Stayz's holiday home rentals are the perfect base for your sightseeing activities.
Why should I book my holiday rental house with Stayz?
Booking your holiday home rental with Stayz means you'll have the entire property to yourselves — your own private space, with no distractions or interruptions from other people. Also, our easy payment and cancellation policies give you the freedom to change your plans if required.