Chesapeake Holiday Rentals

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Compare Villas, Resorts, & Rentals in Chesapeake

184 villas and rentals
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Luxury Holiday Rentals in Chesapeake

Over 175+ Luxury Holiday Rentals in or Near Chesapeake
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Top-Rated Holiday Rentals with a Pool in Chesapeake

Over 50+ The Best Private Villas and Holiday Rentals in Chesapeake with a Pool
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Pet-Friendly Holiday Rentals in Chesapeake

Over 53+ Pet-Friendly Holiday Rentals in or Near Chesapeake
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Large Holiday Rentals and Private Villas in Chesapeake

Over 7+ Large Holiday Rentals and Private Villas in or Near Chesapeake
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Wheelchair Accessible Holiday Homes in Chesapeake

Over 58+ Wheelchair Accessible Holiday Homes in or Near Chesapeake
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Chesapeake Private Villas and Holiday Homes Under $200

Over 90+ Chesapeake Private Villas and Holiday Homes Under $200
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Instantly Bookable Holiday Homes in Chesapeake

Over 27+ Instantly Bookable Holiday Homes in or Near Chesapeake
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Book a Last Minute Place to Stay in Chesapeake

About Casai's Private Villas and Holiday Rentals in Chesapeake

Discover more than 184 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 610.54 ft², with nightly prices averaging US $233.

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 near the Chesapeake, VA


Deep Creek South 154 Properties
Cahoon Plantation Golf Course 134 Properties
Adventure Kayak Tours Day Tours 124 Properties
Chesapeake City County 121 Properties
Portlock Galleries at SoNo 119 Properties
Chesapeake Veterans' Memorial 119 Properties
Chesapeake City Hall 118 Properties
Great Bridge 106 Properties
Western Branch North 71 Properties
Greenbrier West 66 Properties
South Norfolk 58 Properties
Greenbrier East 24 Properties

There are 184 Chesapeake, VA Holiday Rentals

Recently Booked Holiday 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.com holiday rentals are available in Chesapeake?

As of 2026, Casai boasts over 184 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 24
Greenbrier West Vacation Rentals in Chesapeake, Virginia 66
Western Branch North Vacation Rentals in Chesapeake, Virginia 71
Deep Creek South Vacation Rentals in Chesapeake, Virginia 154
Great Bridge Vacation Rentals in Chesapeake, Virginia 106
Churchland Vacation Rentals in Chesapeake, Virginia 66
Great Bridge East Vacation Rentals in Chesapeake, Virginia 27