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Countryside Summer Rentals, Cottages & Cabins

Book a Place to Stay in Countryside for Your Summer Getaway

About Countryside Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Countryside are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Countryside with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Countryside Luxury Rentals

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

In 2025, PickleTrip offers 385 summer rentals in or around Countryside. 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 Countryside is $256. Check the full list of summer accommodations in Countryside.
There are 385 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

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

Check all holiday rentals with a pool in Countryside on PickleTrip.

Yes, We have 385 summer rental homes in Countryside and types of place to stay in Countryside include:

  • Vacation Homes: 385 available for rent
  • Villas: 385 Rentals available for rent
  • Holiday Apartments: 385 Rentals available for rent
  • Hotels with Suites: 385 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Countryside. 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 Countryside.