Renovated Cottage on Court: 3 blocks to historic downtown square

Winterset, Iowa
$244 avg/night
Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

Our renovated 1910 Cottage on Court is more than just a place to stay; it’s a home where memories are made. This charming 2-bedroom, 1.5-bath cottage blends historic charm with modern amenities for a perfect stay. Nestled just 3 blocks from the downtown square, you’re close to shops, cafes, and attractions like the John Wayne Birthplace and Quilt Museum. Book your stay today and discover the allure of our charming cottage in the heart of historic Winterset.

Our cottage offers several cozy spots for you to unwind. Sip your morning coffee on the sun porch, unwind with a glass of wine on the back deck, or curl up with a book and people watch from the front porch. Each space is designed to help you feel at home and make the most of your stay.
The fully equipped kitchen invites you to prepare a delicious meal - or just order pizza - we won't judge.

Key Features:

*Charming 1910 cottage with original hardwood floors and woodwork.
*Two bedrooms and main bath located upstairs, Sofa sleeper and half bath on main level.
*Comfortably sleeping up to six guests.
*Updated kitchen with new fixtures and modern appliances.
*Nostalgic sun porch and inviting back deck for relaxation.
*Front porch perfect for enjoying your morning coffee.
*Walking distance to courthouse square, shops, cafes, and restaurants.
*Close to John Wayne Birthplace, Madison County Historical Museum, and Winterset City Park with 1 of 6 Madison Co. Covered Bridges. Embrace the spirit of Robert and Francesca with a picnic in the park, a scene straight out of The Bridges of Madison County.
*Take a short drive to our renowned local wineries.
*Multiple parks with access to hiking trails, fishing, and kayaking.

Whether you're here for a romantic getaway, a family vacation, or simply to explore the historic charm of Winterset, our cottage offers a welcoming and comfortable retreat. Book your stay today and create lasting memories in our charming 1910 cottage. We look forward to hosting you!

Notes - no smoking or vaping on premises. We don't allow pets.

Stairs are required to enter the cottage and to access both bedrooms and the main bath.

Entire home is available to guests except the garage and basement that houses the owner's closet. Basement is available as emergency shelter.

We are local residents of Madison County and can give you tips for best shopping, restaurants and cafes.
We can direct you to multiple locations within the area. Just ask!

As co-owners of White Cottage Market, an occasional vintage shop, we offer you an exclusive private shopping experience. Text or call to schedule a time!

35 min. to Jordan Creek Mall in West Des Moines
40 min to Des Moines Airport.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Locally-owned & Organized Tours & Activities Recycling Reusable Coffee/tea Filters Uses Some LED Lighting
  • KITCHEN

    Coffee Grinder Dishwasher Microwave Oven Paper Towels Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Outdoor Furniture Patio
  • BATHROOMS

    1.5 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Cycling Nearby Fishing Nearby Hiking Nearby Hunting Nearby
  • ENTERTAINMENT

    Books Games Smart TV
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Stair Gate Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village Near A Hospital
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Area Rugs In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Karen E.

    Submitted May 6, 2026

    Stayed May 3, 2026

    It is a wonderful place to stay. It was extremely clean. The decor and atmosphere was very calm and relaxing. The host keep us informed and reached out to see if we had any needs. It is a perfect place to stay.

  • Paul H.

    Submitted Sep 28, 2025

    Stayed Sep 26, 2025

    Wonderful house. Great location , quiet beautiful neighborhood. Love the porch/sunroom for morning coffee. Meticulously maintained and decorated. Have already booked another stay here.Thanks!

  • Leigh P.

    Submitted Sep 23, 2025

    Stayed Sep 21, 2025

    Such a lovely property! Everything you need and want in a beautiful setting and neighborhood! Just a little walk to the square. Would absolutely stay again if ever in this area!

  • mandy h.

    Submitted Aug 24, 2025

    Stayed Aug 21, 2025

    This home was beautifully redone. It keeps the charm of the original home yet had all the modern conveniences. The kitchen is fully stocked with a full set of pans and bake ware which is terrific. It also has full service for plate ware. I think eight but I didn’t count that. We were three blocks from the town square and the neighborhood is beautiful so we walked just about everywhere. We use Vrbo listings almost exclusively and this home is the best we have seen. Book eatly for your event because you won’t find better and it books out quite far.

  • Emily P.

    Submitted Aug 17, 2025

    Stayed Aug 15, 2025

    Lovely home. All the needed essentials and more were stocked to make our stay perfect. Perfect distance to walk to town. All in all perfection.

  • Danielle K.

    Submitted Jul 29, 2025

    Stayed Jul 27, 2025

    This felt like home! Thank you for thinking of everything and the girls loved the play space/retreat. Loved being so close to downtown and can't wait to come again!

  • Cara M.

    Submitted Jul 23, 2025

    Stayed Jul 17, 2025

    Very lovely place. Nice details, including coffee grinder and moka pot.

  • CJ L.

    Submitted Jul 9, 2025

    Stayed Jul 5, 2025

    Wonderful property.

  • Patsy W.

    Submitted Jul 2, 2025

    Stayed Jun 25, 2025

    Definitely recommend

  • Lynn A.

    Submitted Jun 21, 2025

    Stayed Jun 17, 2025

    Winterset Iowa, Bridges of Madison County, just like the movie Perfect small town with lots of history Renovated Cottage on the Square perfect place to stayI would give this a 10 star

  • Kami W.

    Submitted Jun 18, 2025

    Stayed Jun 13, 2025

    Super cute and clean cottage! We truly enjoyed our stay and Jane was wonderful to work with!

  • Robert G.

    Submitted Jun 11, 2025

    Stayed May 22, 2025

    Everything was amazing! Cute, comfortable and the host certainly went above and beyond to ensure a pleasant stay.

  • Marlene J.

    Submitted Jun 4, 2025

    Stayed May 27, 2025

    The cottage renovation is beautifully done, love the fact they kept the original woodwork and antique pieces of furniture. Love the decorations! Loved setting out on the porch and deck, listening to the birds and watching bunnies. I have used VRBO since 2000, the cottage has been the cleanest we have stayed at. Location was perfect, walkable to downtown, people in Winterset are so friendly. Montrose drug store has a great, affordable breakfast. Be patient, one lady may be the one taking your order, cooking it and taking your money, wow! I love Winterset and will definitely stay at the cottage again!! Oh and check out the photo album showing the history of the cottage, so neat! Thank you Jane!!

  • Helen C H.

    Submitted May 8, 2025

    Stayed Apr 25, 2025

    Great location, cute house.

  • Jeanne W.

    Submitted Oct 22, 2024

    Stayed Oct 18, 2024

    Cottage on Court is a quaint house with comfortable beds and convenient remote-control ceiling lights and fans in the 2 bedrooms. It was perfect for our quilt retreat weekend.

  • Randy W.

    Submitted Oct 18, 2024

    Stayed Oct 11, 2024

    Quiet & Relaxing

  • Mark B.

    Submitted Sep 17, 2024

    Stayed Sep 13, 2024

    Words cannot express the stay at the Cottage in Winterset IA. But for any John Wayne fan it is a must to visit and walk around the very town he was born in. But Winterset is more than a museum location, its like stepping back in time where everything slows up and the Cottage is the perfect place just a short walk to the town square and the people or so friendly and welcoming. Again, you will not find a better place to stay in Winterset, IA.

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Total

Includes taxes and fees
$258+
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