Search Villas in Chesapeake Bay

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select Chesapeake Bay Villas

Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do villas in Chesapeake Bay cost?
Prices for villas in Chesapeake Bay range between and per night. Whatever your budget, you're sure to find a place that suits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Chesapeake Bay?
Choose from villas in Chesapeake Bay. Whether you're escaping with relatives or a group of pals, and wherever your travels take you, Expedia can help you secure your perfect fit.
Why book your villa in Chesapeake Bay with Expedia?
Reserving a villa in Chesapeake Bay is as simple as working out your travel dates and picking the option that satisfies your needs. Want something affordable or upmarket, or a stay that also comes with a laundry and kitchen? Use Expedia's search filters to narrow your results and find the perfect fit.