Chesapeake vacation rentals

Find and compare great deals on vacation rentals in Chesapeake from hundreds of travel sites

Chesapeake, VA, United States
Nov 30 — Dec 12
Chesapeake, VA, United States
Tue 11/30
Wed 12/1
...and more

Tips for booking a vacation rental in Chesapeake

Cheapest month:June
Most expensive month:May
Average price in Chesapeake:$308/night
Absolute cheapest price found:$101/night
Cheapest day:Tuesday
Most expensive day:Thursday
$156 - $836
Average price per night. Prices are not fixed and may vary with time.
$101 - $546
Average price per night. Prices are not fixed and may vary with time.

Chesapeake vacation rental FAQs

  • How much does a vacation rental in Chesapeake cost?

    $309 per night is how much a vacation rental in Chesapeake costs, on average. $101 per night was the cheapest price recently found by our users, though anything for $305 per night or less is a good deal. Keep in mind that Chesapeake vacation rental prices fluctuate throughout the year: the most expensive month to book is August, and the cheapest time to book is November.

  • What part of Chesapeake is best to stay in?

    The best neighborhood to stay in Chesapeake is Ocean View, according to our user data. 56% of our users who looked for vacation rentals in Chesapeake searched for properties in the Ocean View area. If you’re also interested in booking a vacation rental in Ocean View, consider the Rustic Rooftop Delight - Bay Front 2 Bedroom Apts - the neighborhood’s most popular rental property.