166+ Private Villas and Holiday Rentals in Chesapeake |
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  2. Virginia
  3. Norfolk - Virginia Beach
  4. Chesapeake

Chesapeake Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chesapeake

Discover more than 166 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 452.63 ft², with nightly prices averaging US $190.

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.

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Top Accommodation Types in Chesapeake

Type Count
Vacation Homes 56
Holiday Apartments 21
Cottages 2

Use these Quick Filters to Find a Holiday Rental in Chesapeake

★ 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.

Weather in Chesapeake, VA

View the weather forecast for Chesapeake before booking your Chesapeake 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, VA

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


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
Float First
Cahoon Plantation Golf Course
Adventure Kayak Tours Day Tours
Lake Drummond
Chesapeake Regional Medical Center
Virginia Beach Boardwalk
Naval Station Norfolk

Other Places to Stay in Chesapeake, VA


Great Bridge East 535 Properties
Cahoon Plantation Golf Course 170 Properties
Deep Creek South 165 Properties
Chesapeake City County 162 Properties
Portlock Galleries at SoNo 154 Properties
Chesapeake Veterans' Memorial 154 Properties
Great Bridge 137 Properties
Greenbrier West 82 Properties
South Norfolk 80 Properties
Jolliff 45 Properties
Greenbrier East 38 Properties
Western Branch North 26 Properties

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 holiday rentals have private pools in Chesapeake?

Discover a selection of holiday rentals with private pools near Chesapeake 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 are best for families?

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

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

As of 2025, Casai boasts over 166 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) 
Neighborhood Property Count
Greenbrier East Vacation Rentals in Chesapeake, Virginia 38
Western Branch North Vacation Rentals in Chesapeake, Virginia 26
Greenbrier West Vacation Rentals in Chesapeake, Virginia 82
Great Bridge Vacation Rentals in Chesapeake, Virginia 137
Deep Creek South Vacation Rentals in Chesapeake, Virginia 165
Churchland Vacation Rentals in Chesapeake, Virginia 73
Great Bridge East Vacation Rentals in Chesapeake, Virginia 535

People Also Ask

There are 166 Chesapeake, VA Holiday Rentals

Recently Booked Holiday Rentals in Chesapeake