Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

Winterset Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Winterset Vacation Homes

Hawthorne Hideaway is a Charming 3-bedrm bed & breakfast in West DSM with WiFi

The price is CA $145
CA $398 total
includes taxes & fees
Aug 24 - Aug 25
Hawthorne Hideaway is a Charming 3-bedrm bed & breakfast in West DSM with WiFi

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

The price is CA $169
CA $484 total
includes taxes & fees
Aug 25 - Aug 26
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

The Kirkwood - Cozy 2bdrm Oasis

10.0 out of 10, Exceptional, (8)
"Everything was smooth and easy, the hosts provided all communications quickly and out Frenchie, Kyla loved the backyard play! "
The price is CA $113
CA $324 total
includes taxes & fees
Aug 25 - Aug 26
The Kirkwood - Cozy 2bdrm Oasis

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

7.4 out of 10, Good, (3)
"Great stay, apartment was clean and spacious, and a great location for the senior games venues. Clayton was a gracious host and communication was clear and concise. Definitely recommend."
The price is CA $144
CA $246 total
includes taxes & fees
Aug 23 - Aug 24
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

The Hen House Country Living with Farm Life Appeal Indianola, IA

10.0 out of 10, Exceptional, (7)
"Our host was amazing. Went above to make sure we had a great stay. Very personable..We both enjoyed visiting with her and learning more about the area. We will definitely return to the Hen House"
The price is CA $187
CA $262 total
includes taxes & fees
Aug 29 - Aug 30
The Hen House Country Living with Farm Life Appeal Indianola, IA

A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!

10.0 out of 10, Exceptional, (22)
"We were in town for a concert at the Iowa State Fair, and this location and home was just perfect for our group of four. Highly recommend!"
The price is CA $139
CA $304 total
includes taxes & fees
Aug 24 - Aug 25
A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!

Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

2.0 star property
8.8 out of 10, Excellent, (26)
"Wonderful property and host! "
The price is CA $147
CA $403 total
includes taxes & fees
Aug 24 - Aug 25
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Beautiful home minutes from downtown!

9.2 out of 10, Wonderful, (15)
"My family and I had a nice stay. The house was spot on to the description, and you can tell the host goes above and beyond to make guests feel comfortable. "
The price is CA $162
CA $385 total
includes taxes & fees
Aug 26 - Aug 27
Beautiful home minutes from downtown!

Centrally Located Wooded A-Frame

10.0 out of 10, Exceptional, (1)
"So much fun enjoying the yard, cooking, and visiting the nearby lake! Excellent communication from our host! The house is amazing and beautiful! "
The price is CA $185
CA $354 total
includes taxes & fees
Sep 11 - Sep 12
Centrally Located Wooded A-Frame

The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house for our family to stay and gather between weddings events! Easy to get to and had lots of space to hang out. "
The price is CA $222
CA $595 total
includes taxes & fees
Aug 24 - Aug 25
The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown