Entire home
Renovated Cottage on Court: 3 blocks to historic downtown square
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Reviews
10 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 6
Popular amenities
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.
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
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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.
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
We should mention
This property does not have any lifts
About the area
Winterset
Winterset is home to this cottage. West Grand Golf 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 Jordan West. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with hiking, cycling and hunting.

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
Restaurants
- Casey's General Store - 17 min walk
- McDonald’s - 19 min walk
- Casey's General Store - 9 min walk
- Urban Taproom & Grill - 3 min drive
- The Sports Page - 19 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
2 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jun 2025
Verified
10/10 Excellent
Leigh P.
23 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Leigh P.
Stayed 2 nights in Sep 2025
Verified
10/10 Excellent
Kami W.
18 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kami W.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Cara M.
23 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cara M.
Stayed 2 nights in Jul 2025
Verified
10/10 Excellent
Helen C H.
8 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute house near downtown
Helen C H.
Stayed 2 nights in Apr 2025
Verified
10/10 Excellent
Danielle K.
29 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Danielle K.
Stayed 2 nights in Jul 2025
Verified
10/10 Excellent
Paul H.
28 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paul H.
Stayed 2 nights in Sep 2025
Verified
10/10 Excellent
Emily P.
17 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Emily P.
Stayed 2 nights in Aug 2025
Verified
10/10 Excellent
Robert G.
11 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Exceptional!!!
Robert G.
Stayed 3 nights in May 2025
Verified
10/10 Excellent
CJ L.
9 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Bridges
CJ L.
Stayed 4 nights in Jul 2025
Verified
10/10 Excellent
Lynn A.
21 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
10 Star Cottage on the Square
Lynn A.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Randy W.
18 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing
Randy W.
Stayed 2 nights in Oct 2024
Verified
10/10 Excellent
Jeanne W.
22 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Convenient location
Jeanne W.
Stayed 2 nights in Oct 2024
Verified
10/10 Excellent
Mark B.
17 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Step back in time: John Wayne Birthplace Bucket List and Birthday
Mark B.
Stayed 2 nights in Sep 2024
Verified
10/10 Excellent
mandy h.
24 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
mandy h.
Stayed 3 nights in Aug 2025
Verified
10/10 Excellent
Diane W.
31 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming & updated
Diane W.
Stayed 4 nights in Jul 2024
Verified
10/10 Excellent
Marlene J.
4 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning!
Marlene J.
Stayed 5 nights in May 2025
About the host
Hosted by Jane Dawson
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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