170+ Chesapeake City County Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chesapeake City County

Discover more than 170 holiday rentals in Chesapeake City County. Rent By Owner holiday homes has everything you need to find a place to stay near Chesapeake City County, VA.

Whether you are looking for luxury villas in Chesapeake City County, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Chesapeake City County with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Chesapeake City County for families, large parties, or private owner accommodations for long or short trips. Chesapeake City County Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Chesapeake City County with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

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Frequently Asked Questions About Chesapeake City County Holiday Rentals

There are a lot of options in Chesapeake City County. If you plan on staying in the Chesapeake City County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Chesapeake City County:

There are many holiday rentals available in Chesapeake City County; however, here are a few of the most popular holiday homes listed in Chesapeake City County on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Chesapeake City County to find one that works for you.
Yes, there are 170 self-catering family homes and holiday rentals in Chesapeake City County.
There are more than 170 luxury holiday homes in or near Chesapeake City County, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: