Vacation rentals in Winterset

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Top-rated vacation rentals in Winterset

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Winterset

5.0 out of 5 average rating, 44 reviews

Rosehaven

Enjoy the nostalgic small town charm of Winterset, Iowa while staying at Rosehaven, within walking distance to the town square. Between the historic Madison County covered bridges in the area, the John Wayne museum and his preserved birthplace, as well as the numerous wineries and local events - Winterset is full of reasons to visit and stay at Rosehaven - a short 30 min. drive to Des Moines. Rosehaven is easy to find, with plenty of room for up to 5 or 6 guests. We look forward to having you!

Aug 31 – Sep 7

R2,697 ZAR per night
Guest favorite

Loft in Winterset

5.0 out of 5 average rating, 55 reviews

Aerie Loft Apartment with view that sleeps 7

This elevated second story apartment has an incredible view of the historic downtown square and courthouse. Bring your group to be in a centralized location near dining/bars , shopping, museums, and a movie theatre. Accommodations for a group of seven is ideal for getaways or special occasions. The unique relief art sculpture of a tree and eagles will captivate you. A full kitchen with all the essentials. 6 beds and spacious 3/4 bath and a second 3/4 bath opened for 5 or more guests.

Dec 25 – Jan 1

R2,857 ZAR per night
Guest favorite

Home in Winterset

5.0 out of 5 average rating, 15 reviews

The Home Place

The Home Place, built in 1895, sits three blocks from the Winterset square. It showcases local businesses and Winterset history while offering modern amenities and the comforts of home. Soaps and cleaning supplies are as fragrant free as possible, allowing for a near hypoallergenic haven. No pets for this reason. We offer a king bed, a queen bed, a dedicated office, and a handicapped entrance ramp. Cots, Pack-N-Play, and baby gates are available upon request. Welcome to The Home Place.

Nov 9 – 16

R2,318 ZAR per night

Popular amenities for Winterset vacation rentals

Stay near Winterset's top sights

John Wayne Birthplace & Museum14 locals recommend
Winterset City Park4 locals recommend
Hy-Vee5 locals recommend
Sports Page4 locals recommend
Northside Cafe5 locals recommend
Mi Pueblito5 locals recommend

Other great vacation rentals in Winterset

Guest favorite

Home in Winterset

4.98 out of 5 average rating, 40 reviews

Hygge House in the ❤️ of historic Winterset

Mar 9 – 16

R3,524 ZAR per night
Guest favorite

Home in Winterset

5.0 out of 5 average rating, 14 reviews

The Little Red House

Aug 9 – 16

R2,813 ZAR per night
Guest favorite

Farm stay in Winterset

4.95 out of 5 average rating, 21 reviews

Entire farmhouse in the country

Dec 19 – 26

R4,356 ZAR per night
Guest favorite

Guesthouse in Winterset

5.0 out of 5 average rating, 23 reviews

Luxury Guest Home in Beautiful Madison County

Jan 9 – 16

R4,623 ZAR per night
Guest favorite

Tiny home in Norwalk

5.0 out of 5 average rating, 13 reviews

Charming Waterfront Tiny House & Sauna

Jun 24 – Jul 1

R1,995 ZAR per night
Guest favorite

Home in Winterset

5.0 out of 5 average rating, 58 reviews

The Bungalow in Winterset

Feb 13 – 20

R4,437 ZAR per night
Guest favorite

Cabin in Winterset

4.98 out of 5 average rating, 47 reviews

Cabin on 10 Wooded Acres to Relax, Unwind & Gather

Jul 17 – 24

R10,113 ZAR per night
Guest favorite

Cabin in Saint Charles

4.92 out of 5 average rating, 13 reviews

Country peace

Nov 25 – Dec 2

R1,675 ZAR per night
Guest favorite

Home in Cumming

4.97 out of 5 average rating, 32 reviews

Little Shouse On The Prairie

Feb 7 – 14

R2,466 ZAR per night
Guest favorite

Apartment in Stuart

5.0 out of 5 average rating, 35 reviews

The 1894 by Doe A Deer

Sep 16 – 23

R2,113 ZAR per night
Guest favorite

Cabin in Cumming

5.0 out of 5 average rating, 96 reviews

Iconic Iowa - A 1920 Built Country Cabin

Sep 9 – 16

R2,919 ZAR per night
Guest favorite

Barn in Peru

5.0 out of 5 average rating, 13 reviews

Clanton Creek ‘Cabin’

Jan 6 – 13

R3,265 ZAR per night

Quick stats about vacation rentals in Winterset

Total rentals

10 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.4K reviews

Nightly prices starting at

R190 ZAR before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County
  5. Winterset