See all properties
Entire home

Renovated Cottage on Court: 3 blocks to historic downtown square

Photo gallery for Renovated Cottage on Court: 3 blocks to historic downtown square

Welcome to Cottage on Court - street parking available in front
completely renovated kitchen featuring custom cabinets and butcherblock counters
this dining area blends rustic charm with modern elegance.
Vintage built-in cabinet turned dry bar. Just add your beverage of choice!
Serene bathroom oasis featuring a soaking tub and a sleek glass-enclosed shower

Reviews

10 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Winterset, IA
  • Place, Madison County Courthouse
    ‪5 min walk‬
  • Place, John Wayne Birthplace Museum
    ‪8 min walk‬
  • Place, Cutler-Donahoe Covered Bridge
    ‪18 min walk‬
  • Airport, Des Moines, IA (DSM-Des Moines Intl.)
    ‪40 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Office 1

1 Queen Sofa Bed

1 bathroom, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area

About this property

Renovated Cottage on Court: 3 blocks to historic downtown square

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.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Exterior
The Little Brick House - Walkable to the Square Dining & Shopping
Winterset
  • Washing machine
  • Dryer
  • Air-conditioning
10.0 out of 10, Exceptional, (9 reviews)
The Little Brick House - Walkable to the Square Dining & Shopping

House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Check out time is 11 am. Place any dirty dishes in the sink or dishwasher. Bag up garbage if needed. Please don't strip the beds. Place all towels in the hamper in the bathroom
Failure to complete these may result in a negative review from the host.
No smoking or vaping (tobacco or marijuana) in home or any porch or deck. No illegal substances on premises. No candles please
No hair color or process done at the cottage
Guests found in violation of any of these rules may be subject to additional charges, including but not limited to cleaning fees, and repair costs.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Winterset

Winterset is home to this cottage. Pammel State Park and Topgolf are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Jordan Creek Town Center and West Glen Town Center. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with hiking, hunting and cycling.
View more Cottages in WintersetOpens in a new window
Map
Winterset, IA

What's nearby

  • Madison County Courthouse - 5 min walk - 0.4 km
  • John Wayne Birthplace Museum - 8 min walk - 0.7 km
  • Cutler-Donahoe Covered Bridge - 18 min walk - 1.5 km
  • Clark Tower - 2 min drive - 2.5 km
  • The Winterset Stage - 3 min drive - 1.8 km

Getting around

  • Des Moines International Airport (DSM) - 43 min drive

Restaurants

  • ‪Casey's General Store - ‬17 min walk
  • ‪McDonald’s - ‬19 min walk
  • ‪Casey's General Store - ‬9 min walk
  • ‪Petite Cafe - ‬4 min walk
  • ‪Urban Taproom & Grill - ‬3 min drive

Frequently asked questions

Is Renovated Cottage on Court: 3 blocks to historic downtown square pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Renovated Cottage on Court: 3 blocks to historic downtown square?

As of 3 May 2026, prices found for a 1-night stay for 2 adults at Renovated Cottage on Court: 3 blocks to historic downtown square on 27 October 2026 start from NZ$346, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Renovated Cottage on Court: 3 blocks to historic downtown square?

On-site parking is available at the property.

What time is check-in at Renovated Cottage on Court: 3 blocks to historic downtown square?

Check-in begins at 3:00 PM.

What time is check-out at Renovated Cottage on Court: 3 blocks to historic downtown square?

Checkout is at 11:00 AM.

Where is Renovated Cottage on Court: 3 blocks to historic downtown square located?

Situated in Winterset, this cottage is within a 10-minute walk of Madison County Courthouse and John Wayne Birthplace Museum. Pammel State Park and Roseman Bridge are also within 12 miles (20 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Patsy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Place was Wonderful!!!

Definitely recommend
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Leigh P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Kami W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super cute and clean cottage! We truly enjoyed our stay and Jane was wonderful to work with!
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Helen C H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute house near downtown

Great location, cute house.
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Cara M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very lovely place. Nice details, including coffee grinder and moka pot.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Danielle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Paul H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Robert G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceptional!!!

Everything was amazing! Cute, comfortable and the host certainly went above and beyond to ensure a pleasant stay.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Emily P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

CJ L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bridges

Wonderful property.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Lynn A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

10 Star Cottage on the Square

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
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Randy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing

Quiet & Relaxing
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Jeanne W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Convenient location

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.
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Mark B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Step back in time: John Wayne Birthplace Bucket List and Birthday

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.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

mandy h.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Diane W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming & updated

This cottage has such an Iowa charm, yet it has been recently updated. It was extremely clean and the host left all of the essentials to anticipate what might be needed during our stay. The host was quick and thoughtful to respond to messages. The location, in my opinion, is the best in Winterset. It is only a couple of blocks to walk to the Winterset square where the Courthouse and shops are. The neighborhood is very safe with beautiful homes and well-kept landscapes. It is very quiet. My husband and I cannot wait to return sometime to stay there again!
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Marlene J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stunning!

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!!
Stayed 5 nights in May 2025

About the host

Hosted by Jane Dawson

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback