Southwold Summer Rentals, Cottages & Cabins

Book a Place to Stay in Southwold for Your Summer Getaway

About Southwold Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Southwold 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 Southwold 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™.

Show more
Show less

Frequently Asked Questions About Southwold Luxury Rentals

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

In 2025, PickleTrip offers 726 summer rentals in or around Southwold. 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 Southwold is $480. Check the full list of summer accommodations in Southwold.
There are 726 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 Southwold that have a private or indoor pool:

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

Yes, We have 726 summer rental homes in Southwold and types of place to stay in Southwold include:

  • Vacation Homes: 726 available for rent
  • Villas: 726 Rentals available for rent
  • Holiday Apartments: 726 Rentals available for rent
  • Hotels with Suites: 726 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Southwold. 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 Southwold.