Chesapeake Summer Rentals, Cottages & Cabins

Book a Place to Stay in Chesapeake for Your Summer Getaway

About Chesapeake Summer Rental on SunSkiResorts

SunSki's selection of summer rentals in Chesapeake promises the ideal setting for your next seasonal escape. We offer a diverse array of properties boasting enticing features such as private pools, indoor/outdoor swimming facilities, hot tubs, WiFi, beachfront access, and more. Whether you're journeying with family, friends, or a larger group, we have a rental perfectly tailored to your requirements.

Immerse yourself in the epitome of summer leisure in Chesapeake with SunSki. Our summer rental accommodations are meticulously curated to ensure utmost comfort and relaxation. From chic condos and opulent resorts to charming villas, quaint bungalows, cozy cabins, RVs, and cottages, we present a spectrum of options to match your vacation vision. Discover your idyllic summer retreat with SunSki.

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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, SunSki offers 116 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 116 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with SunSkiResorts.

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 SunSkiResorts.

Yes, We have 116 summer rental homes in Chesapeake and types of place to stay in Chesapeake include:

  • Vacation Homes: 116 available for rent
  • Villas: 116 Rentals available for rent
  • Holiday Apartments: 116 Rentals available for rent
  • Hotels with Suites: 116 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.