Pleasant Prairie Cottage Rentals & Holiday Homes

Find the best cottages in Pleasant Prairie - We found 81 exact matches

About Pleasant Prairie Cottage Rentals on PickleTrip

Searching for cottages to rent near Pleasant Prairie? PickleTrip™ features more than 81 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Pleasant Prairie have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Pleasant Prairie.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

PickleTrip™ boasts of 81 holiday cottages and places to stay in Pleasant Prairie. The site provides unique Airbnb, VRBO, pickleball-ready cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday — all fitting within your budget.

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Frequently Asked Questions About Pleasant Prairie Rental Cottages

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

The average cost for a cottage rental in Pleasant Prairie is $461 per night. PickleTrip has a wide list of great cottages near Pleasant Prairie that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Pleasant Prairie that allow you to bring your pet:

See all pet-friendly vacation rentals in Pleasant Prairie on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Pleasant Prairie to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 81 private swimming pools or cottages with indoor pools in the Pleasant Prairie area along with other great amenities.
About 81 cottages in Pleasant Prairie boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Pleasant Prairie on PickleTrip
Yes, there are luxury cottages in Pleasant Prairie. Find more luxury, lakefront, winter, & last-minute cottage rentals near Pleasant Prairie.