Renovated Cottage on Court: 3 blocks to historic downtown square

Exceptional

2 bedrooms1+ bathroomSleeps 6

Popular amenities

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

Explore the area

Winterset, IA

Place, Madison County Courthouse
‪5 min walk‬
Place, John Wayne Birthplace Museum
‪8 min walk‬
Place, The Winterset Stage
‪3 min drive‬
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

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 prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen

Washing machine

Dryer

Free WiFi

Air conditioning

Outdoor space

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Washing machine
Dryer
Air-conditioning

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.

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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.

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 Bridgewood Plaza. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with hiking, cycling and hunting.

View more Cottages in Winterset

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
‪Urban Taproom & Grill - ‬3 min drive
‪The Sports Page - ‬19 min walk

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 29 Mar 2026, prices found for a 1-night stay for 2 adults at Renovated Cottage on Court: 3 blocks to historic downtown square on 30 Jun 2026 start from £127, 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. Roseman Bridge is 9.6 mi (15.5 km) away.

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

10/10 Excellent

Patsy W.

2 Jul 2025

8 May 2025

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.

31 Jul 2024

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.

4 Jun 2025

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

Languages:

English

Premier Host

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Renovated Cottage on Court: 3 blocks to historic downtown square

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Reviews

Popular amenities

Explore the area

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

Bedroom 2

Office 1

1 bathroom, 1 half bathroom

Bathroom 1

Bathroom 2

Spaces

About this property