132+ Lake Sherwood Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Lake Sherwood

Discover more than 132 holiday rentals in Lake Sherwood. PickleTrip™ holiday homes has everything you need to find a place to stay near Lake Sherwood, WI.

Whether you are looking for luxury villas in Lake Sherwood, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Lake Sherwood with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Lake Sherwood for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Lake Sherwood with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Lake Sherwood Holiday Rentals

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

There are many holiday rentals available in Lake Sherwood; however, here are a few of the most popular holiday homes listed in Lake Sherwood on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Lake Sherwood to find one that works for you.
Yes, there are 132 self-catering family homes and holiday rentals in Lake Sherwood.
There are more than 132 luxury holiday homes in or near Lake Sherwood, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 132 pet friendly rentals that are available in Lake Sherwood.