171+ Private Villas and Holiday Rentals in Chesapeake City County |
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Chesapeake City County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chesapeake City County

Discover more than 171 vacation rentals available in Chesapeake City County. 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 City County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesapeake City County, 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 City County. On average, places to stay near Chesapeake City County offer 442.3 ft², with nightly prices averaging ZA R3,230.

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

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Top Accommodation Types in Chesapeake City County

Type Count
Vacation Homes 59
Holiday Apartments 20
Cottages 2

Use these Quick Filters to Find a Holiday Rental in Chesapeake City County

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chesapeake City County.

Weather in Chesapeake City County, VA

View the weather forecast for Chesapeake City County before booking your Chesapeake City County Vacation Rentals to confirm your best time to go.

December - February
High 62°F       Low 35°F
March - May
High 76°F       Low 41°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 44°F

Top Attractions Around Chesapeake City County, VA

Casai offers a large selection of top attractions around Chesapeake City County . Research things to do on your vacation before you visit Chesapeake City County.


Greenbrier Mall
Chesapeake Square Mall
Great Dismal Swamp National Wildlife Refuge
Chesapeake Conference Center
Chesapeake Veterans' Memorial
Chesapeake City Park
Chesapeake City Hall
Chesapeake Arboretum
Chesapeake Golf Club
Chesapeake Central Library
Jillian's Billiards
Portlock Galleries at SoNo
Oak Grove Lake Park
Cahoon Plantation Golf Course
Float First
Adventure Kayak Tours Day Tours
Lake Drummond
Chesapeake Regional Medical Center
Virginia Beach Boardwalk
Naval Station Norfolk
Virginia Beach Town Center
Hampton Coliseum
Sandbridge Beach
Virginia Beach Convention Center
Old Dominion University
Veterans United Home Loans Amphitheater at Virginia Beach
Ocean Breeze Waterpark
Buckroe Beach and Park
Hampton University
Norfolk State University

Other Places to Stay in Chesapeake City County, VA


Great Bridge East 535 Properties
Chesapeake 193 Properties
Cahoon Plantation Golf Course 170 Properties
Deep Creek South 165 Properties
Chesapeake Veterans' Memorial 154 Properties
Portlock Galleries at SoNo 154 Properties
Great Bridge 137 Properties
South Norfolk 92 Properties
Greenbrier West 82 Properties
Greenbrier East 46 Properties
Jolliff 45 Properties
Western Branch North 33 Properties

Frequently Asked Questions About Chesapeake City County?

What are the top holiday rentals in Chesapeake City County?

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

How many holiday rentals have private pools in Chesapeake City County?

Discover a selection of holiday rentals with private pools near Chesapeake City County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chesapeake City County are best for families?

If you're searching for a family-friendly holiday home in Chesapeake City County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chesapeake City County:

How many Casai.co.za holiday rentals are available in Chesapeake City County?

As of 2025, Casai boasts over 171 properties listed in the Chesapeake City County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesapeake City County.


People Also Ask

There are 171 Chesapeake City County, VA Holiday Rentals

Recently Booked Holiday Rentals in Chesapeake City County