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

We believe finding a vacation rental in Chesapeake Bay 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 Bay

Vacation rentals in Chesapeake Bay

There are 4,216 vacation rentals near Chesapeake Bay for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Chesapeake Bay vacation, you can find 10% rentals under $55/night. Or if you are willing to splurge on a luxury vacation in Chesapeake Bay, there are 422 between $579 and $10,000/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 75 there are short term home and apartment rentals in Chesapeake Bay to fit your Virginia vacation needs. The most popular types of short-term rental homes in Chesapeake Bay are houses, private rooms and apartments. Chesapeake Bay 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), Homeaway,, and many more. Search your travel dates to find available Chesapeake Bay vacation homes for your trip.

Home-types in Chesapeake Bay

Chesapeake Bay has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Chesapeake Bay:
- Oceanfront4,216 vacation rentals
- Beach4,216 vacation rentals
- House2,327 vacation rentals
- Private Room780 vacation rentals
- Condo580 vacation rentals
- Apartment580 vacation rentals
- Hotel279 vacation rentals
- Bed & Breakfast76 vacation rentals
- Villa45 vacation rentals
- Cabin26 vacation rentals

Points of interests in Chesapeake Bay

Chesapeake Bay 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 Bay:
- Bayside History Museum: 37 vacation rentals
- Pleasure House Point: 11 vacation rentals