Chesapeake, VA Holiday Rentals

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Compare Holiday Rentals, Villas & Resorts in Chesapeake

187 villas and rentals
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About Casai's Private Villas and Holiday Rentals in Chesapeake

Discover more than 187 vacation rentals available in Chesapeake. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chesapeake.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesapeake, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chesapeake. On average, places to stay near Chesapeake offer 632.3 ft², with nightly prices averaging CA $327.

With Casai, finding and comparing holiday rentals in Chesapeake is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other Places to Stay in Chesapeake, VA


Greenbrier East 191 Properties
Deep Creek South 160 Properties
Cahoon Plantation Golf Course 134 Properties
Adventure Kayak Tours Day Tours 124 Properties
Chesapeake City County 123 Properties
Portlock Galleries at SoNo 119 Properties
Chesapeake Veterans' Memorial 119 Properties
Chesapeake City Hall 118 Properties
Great Bridge 113 Properties
Western Branch North 71 Properties
Greenbrier West 68 Properties
South Norfolk 61 Properties

There are 187 Chesapeake, VA Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Chesapeake

Frequently Asked Questions About Chesapeake?

What are the top holiday rentals in Chesapeake?

With numerous options available in Chesapeake, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chesapeake:

How many Casai.ca holiday rentals are available in Chesapeake?

As of 2026, Casai boasts over 187 properties listed in the Chesapeake area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesapeake.

Nearby Neighborhood (7)

NeighborhoodProperty Count
Greenbrier East Vacation Rentals in Chesapeake, Virginia 191
Western Branch North Vacation Rentals in Chesapeake, Virginia 71
Greenbrier West Vacation Rentals in Chesapeake, Virginia 68
Deep Creek South Vacation Rentals in Chesapeake, Virginia 160
Great Bridge Vacation Rentals in Chesapeake, Virginia 113
Churchland Vacation Rentals in Chesapeake, Virginia 66
Great Bridge East Vacation Rentals in Chesapeake, Virginia 27