Chesapeake Summer Rentals, Cottages & Cabins

Book a Place to Stay in Chesapeake for Your Summer Getaway

About Chesapeake Summer Rental on Casai.co.za

With 114 summer rental in or near Chesapeake? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.

Our holiday homes and villas in Chesapeake come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.

Searching for a relaxing retreat in Chesapeake to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Chesapeake.

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Frequently Asked Questions About Chesapeake Luxury Rentals

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

In 2025, Casai offers 114 summer rentals in or around Chesapeake. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Chesapeake is $206. Check the full list of summer accommodations in Chesapeake.
There are 114 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.co.za.

Yes, here are some popular summer holiday rentals in Chesapeake that have a private or indoor pool:

Check all holiday rentals with a pool in Chesapeake on Casai.co.za.

Yes, We have 114 summer rental homes in Chesapeake and types of place to stay in Chesapeake include:

  • Vacation Homes: 114 available for rent
  • Villas: 114 Rentals available for rent
  • Holiday Apartments: 114 Rentals available for rent
  • Hotels with Suites: 114 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Chesapeake. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Chesapeake.