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 1,646 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 $87/night. Or if you are willing to splurge on a luxury vacation in Chesapeake Bay, there are 165 between $700 and $8,500/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 vacation rentals in Chesapeake Bay are houses, apartments and hotels. 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:
- Oceanfront1,646 vacation rentals
- Beach1,646 vacation rentals
- House1,076 vacation rentals
- Condo217 vacation rentals
- Apartment217 vacation rentals
- Hotel204 vacation rentals
- Bed & Breakfast42 vacation rentals
- Villa39 vacation rentals
- Cabin10 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: 17 vacation rentals
- Pleasure House Point: 5 vacation rentals