What are the top rated Cottage Rentals in Osceola?

There are a lot of options in Osceola. If you plan on staying in the Osceola area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Osceola: <a href="/property/historic-1880s-home/HA-3211762967" class="class="static-page-link"">Historic 1880s Home</a> <a href="/property/cozy-mother-in-law-apartment/HA-1219132976" class="class="static-page-link"">Cozy Mother-in-Law Apartment</a> <a href="/property/cozy-cabin-for-getaway-on-a-beautiful-lake-1-mile-from-trollhaugen/HA-3213837188" class="class="static-page-link"">Cozy cabin for getaway! On a beautiful lake, 1 mile from Trollhaugen</a> <a href="/property/lake-life-is-calling/HA-3211696985" class="class="static-page-link"">Lake life is Calling</a> <a href="/property/lakefront-osceola-vacation-rental-dogs-welcome/HA-1219842347" class="class="static-page-link"">Lakefront Osceola Vacation Rental - Dogs Welcome!</a> <a href="/property/lake-osceola-retreat-100-acre-private-lake-home/HA-3213592414" class="class="static-page-link"">Lake Osceola Retreat 100-Acre Private Lake Home</a> <a href="/property/great-fishing-sunset-views-lakeside-cabins-joined-by-porch-1-hour-from-tc/HA-3212644574" class="class="static-page-link"">Great fishing &amp; sunset views, lakeside cabins joined by porch. 1 hour from TC</a> <a href="/property/lakefront-osceola-vacation-rental-dogs-welcome/BC-10313930" class="class="static-page-link"">Lakefront Osceola Vacation Rental - Dogs Welcome!</a> <a href="/property/historic-beauty-w-modern-updates-near-taylor-s-falls/HA-3212222453" class="class="static-page-link"">Historic Beauty w Modern Updates Near Taylor&#39;s Falls</a> <a href="/property/lakefront-home-with-6-person-hot-tub/HA-3214229411" class="class="static-page-link"">Lakefront Home with 6-person Hot Tub</a>

How much does it cost to rent a cottage in Osceola?

The average cost for a cottage rental in Osceola is $195 per night. Execstays has a wide list of great cottages near Osceola that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Osceola that allow pets?

Yes, here are the top cottage rentals in Osceola that allow you to bring your pet: Osceola Cottage w/ Dock Situated on Wind Lake Historic 1880s Home Lakefront Osceola Vacation Rental - Dogs Welcome! River Valley Inn & Suites Cozy Mother-in-Law Apartment <a href="/all/usa/wisconsin/osceola" class="class="static-page-link"">See all pet-friendly vacation rentals in Osceola on Execstays</a>

Do you have any rental cottages in Osceola that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Osceola to find one that works for you.

Are there quality cottages in Osceola that have indoor swimming pools?

As of 2026, the data from Execstays shows that there are Over 1 private swimming pools or cottages with indoor pools in the Osceola area along with other great amenities.