The best rentals from the top sites, all in one place

We believe finding a vacation rental in Chesapeake should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Chesapeake

Vacation rentals in Chesapeake

There are 655 vacation rentals near Chesapeake for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Chesapeake vacation, you can find 10% rentals under $43/night. Or if you are willing to splurge on a luxury vacation in Chesapeake, there are 66 between $282 and $2,000/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 90 there are short term home and apartment rentals in Chesapeake to fit your vacation needs. The most popular types of short-term rental homes in Chesapeake are private rooms, houses and condos. Chesapeake has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like Vrbo (Vacation Rentals By Owner),, and many more. Search your travel dates to find available Chesapeake vacation homes for your trip.

Home-types in Chesapeake

Chesapeake has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Chesapeake:

Points of interests in Chesapeake

Chesapeake has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Chesapeake: