Aspen Highlands Summer Rentals, Cottages & Cabins

Book a Place to Stay in Aspen Highlands for Your Summer Getaway

About Aspen Highlands Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Aspen Highlands 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 Aspen Highlands 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 Aspen Highlands Luxury Rentals

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

In 2025, PickleTrip offers 306 summer rentals in or around Aspen Highlands. 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 Aspen Highlands is $2,456. Check the full list of summer accommodations in Aspen Highlands.
There are 306 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 Aspen Highlands that have a private or indoor pool:

Check all holiday rentals with a pool in Aspen Highlands on PickleTrip.

Yes, We have 306 summer rental homes in Aspen Highlands and types of place to stay in Aspen Highlands include:

  • Vacation Homes: 306 available for rent
  • Villas: 306 Rentals available for rent
  • Holiday Apartments: 306 Rentals available for rent
  • Hotels with Suites: 306 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Aspen Highlands. 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 Aspen Highlands.