What are the top rated Cottage Rentals in Winterset?

There are a lot of options in Winterset. If you plan on staying in the Winterset area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Winterset: <a href="/property/charming-winterset-vacation-rental-w-yard-patio/HA-1219954272" class="class="static-page-link"">Charming Winterset Vacation Rental w/Yard &amp; Patio</a> <a href="/property/the-roost-at-speckled-hen-farms/HA-3212933887" class="class="static-page-link"">The Roost at Speckled Hen Farms.</a> <a href="/property/wooded-cottage-on-10-acres-to-explore-and-entertain/HA-3211364518" class="class="static-page-link"">Wooded cottage on 10 Acres to explore and entertain</a> <a href="/property/entire-farmhouse-in-the-country/HA-3212836712" class="class="static-page-link"">Entire farmhouse in the country</a> <a href="/property/holliwell-bridge-retreat-private-spacious-close-to-town-great-for-groups/HA-3213573776" class="class="static-page-link"">Holliwell Bridge Retreat - Private, Spacious &amp; Close to town! Great for Groups!</a> <a href="/property/covered-bridge-haven-3-bedroom-house-with-themed-rooms-in-winterset/HA-3214617389" class="class="static-page-link"">Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset</a> <a href="/property/the-little-brick-house-walkable-to-the-square-dining-shopping/HA-3214807622" class="class="static-page-link"">The Little Brick House - Walkable to the Square Dining &amp; Shopping</a> <a href="/property/charming-1855-stone-farmhouse-retreat-cozy-stays-picturesque-views-await/HA-3214249727" class="class="static-page-link"">Charming 1855 Stone Farmhouse Retreat – Cozy Stays &amp; Picturesque Views Await</a> <a href="/property/charming-winterset-vacation-rental-with-yard-and-patio/BC-11968435" class="class="static-page-link"">Charming Winterset Vacation Rental with Yard and Patio</a> <a href="/property/cobblestone-inn-suites-winterset-ia/EP-10446857" class="class="static-page-link"">Cobblestone Inn &amp; Suites - Winterset, IA</a>

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

The average cost for a cottage rental in Winterset is $204 per night. Montanatravelandtourism has a wide list of great cottages near Winterset that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winterset that allow pets?

Yes, here are the top cottage rentals in Winterset that allow you to bring your pet: Renovated Cottage on Court: 3 blocks to historic downtown square Charming Winterset Vacation Rental w/Yard & Patio Charming Winterset Vacation Rental with Yard and Patio Cobblestone Inn & Suites - Winterset, IA Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset <a href="/all/usa/iowa/winterset" class="class="static-page-link"">See all pet-friendly vacation rentals in Winterset on Montanatravelandtourism</a>

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

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

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

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

Winterset Cottage Rentals By Owner

Renovated Cottage on Court: 3 blocks to historic downtown square

From US $204

10.0 (17 Reviews)

Cottage

Renovated Cottage on Court: 3 blocks to historic downtown square

Air Conditioner
Parking
TV

Winterset Cottage Rentals & Holiday Homes

Find the best cottages in Winterset - We found 1 exact matches

When do you want to travel?