Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

Winterset Holiday 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
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Microwave, oven, stovetop, dishwasher

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

The price is HK$1,127
HK$2,959 total
includes taxes & fees
30 Jul - 31 Jul
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Fridge, microwave, oven, stovetop

• Lively Cottage 2 King Beds 4 Bed 2 Bath •

9.4 out of 10, Exceptional, (14)
"The property was just as advertised. It had everything we needed for our stay. It's in a nice neighborhood and we were very comfortable walking our dog at any time of the day."
The price is HK$932
HK$2,073 total
includes taxes & fees
9 Jul - 10 Jul
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities
Terrace/patio

Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

10.0 out of 10, Exceptional, (32)
"Everything was immaculately clean, all cupboards, drawers were stocked with every essential we could need and our host was easy to communicate with. Definitely would stay again!"
The price is HK$1,900
HK$4,194 total
includes taxes & fees
17 Jul - 18 Jul
Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities
The Hen House Country Living with Farm Life Appeal Indianola, IA
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (4)
"We had a WONDERFUL time at the Hen House! Our girls were overjoyed with all the toys, books, games, and puzzles to play with, not to mention the swings, bikes, fire pit, animals, and everything else! Lori and Lee are AMAZING hosts and truly have got you covered for anything you can think of!There’s absolutely no question that when we come back to Indianola, we’ll be staying here again! "
The price is HK$1,060
HK$1,484 total
includes taxes & fees
9 Jul - 10 Jul
The Hen House Country Living with Farm Life Appeal Indianola, IA
Beautiful home minutes from downtown!
Games room

Beautiful home minutes from downtown!

9.4 out of 10, Exceptional, (13)
"It was a great location and house was pretty nice"
The price is HK$918
HK$2,180 total
includes taxes & fees
15 Jul - 16 Jul
Beautiful home minutes from downtown!
Spacious updated home minutes from Airport and DT!
Property grounds

Spacious updated home minutes from Airport and DT!

7.8 out of 10, Good, (16)
"Perfect for a small group like ours"
The price is HK$954
HK$2,452 total
includes taxes & fees
13 Jul - 14 Jul
Spacious updated home minutes from Airport and DT!
Modern Boho Townhome w/Hidden Reading Nook Near Downtown Des Moines!
Fridge, microwave, oven, stovetop

Modern Boho Townhome w/Hidden Reading Nook Near Downtown Des Moines!

10.0 out of 10, Exceptional, (3)
"I traveled with my adult son back to Iowa for my 35th class reunion and to go to the State Fair. We could not have been happier with this rental. The location is a close distance to everything. The neighborhood is quiet and friendly. Our host was extremely responsive and helpful. The property is well kept and neat. The home itself is well stocked with all the essentials you will need including coffee, creamer, and basic seasonings The beds are some of the most comfortable we have had in any...
The price is HK$824
HK$1,697 total
includes taxes & fees
4 Aug - 5 Aug
Modern Boho Townhome w/Hidden Reading Nook Near Downtown Des Moines!
A Private Boho-Modern Stay Minutes to Downtown w/ KING Bed and Hidden Nook!
Fridge, microwave, oven, stovetop

A Private Boho-Modern Stay Minutes to Downtown w/ KING Bed and Hidden Nook!

10.0 out of 10, Exceptional, (15)
"Everything was great!"
The price is HK$863
HK$1,723 total
includes taxes & fees
23 Jul - 24 Jul
A Private Boho-Modern Stay Minutes to Downtown w/ KING Bed and Hidden Nook!
A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (18)
"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 HK$785
HK$1,653 total
includes taxes & fees
13 Jul - 14 Jul
A Charming Home Minutes to Downtown, Zoo, & Airport with Hidden Reading Nook!
The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
Fridge, microwave, oven, stovetop

The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM

The price is HK$785
HK$1,653 total
includes taxes & fees
13 Jul - 14 Jul
The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
The Kirkwood - Cozy 2bdrm Oasis
Property grounds

The Kirkwood - Cozy 2bdrm Oasis

10.0 out of 10, Exceptional, (6)
"Everything was smooth and easy, the hosts provided all communications quickly and out Frenchie, Kyla loved the backyard play! "
The price is HK$671
HK$1,912 total
includes taxes & fees
13 Jul - 14 Jul
The Kirkwood - Cozy 2bdrm Oasis
Downtown Skyline Views in Modern Townhome with Rooftop Patios
Terrace/patio

Downtown Skyline Views in Modern Townhome with Rooftop Patios

10.0 out of 10, Exceptional, (28)
"We had a great time and an easy stay walking distance from several great spots."
The price is HK$1,562
HK$2,655 total
includes taxes & fees
14 Jul - 15 Jul
Downtown Skyline Views in Modern Townhome with Rooftop Patios
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
Property grounds

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

2.0 star property
8.8 out of 10, Excellent, (22)
"Wonderful property and host! "
The price is HK$975
HK$2,454 total
includes taxes & fees
15 Jul - 16 Jul
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
3-Bedroom Near Downtown w/ Backyard, Pet friendly!
Exterior

3-Bedroom Near Downtown w/ Backyard, Pet friendly!

The price is HK$777
HK$2,013 total
includes taxes & fees
9 Jul - 10 Jul
3-Bedroom Near Downtown w/ Backyard, Pet friendly!
Fun Backyard ~Close to Downtown~Pet Friendly~4BDRM
Fridge, microwave, oven, stovetop

Fun Backyard ~Close to Downtown~Pet Friendly~4BDRM

The price is HK$1,028
HK$2,778 total
includes taxes & fees
9 Jul - 10 Jul
Fun Backyard ~Close to Downtown~Pet Friendly~4BDRM
Spacious 9BR Home~Ideal for Groups~Near Downtown
Fridge, microwave, oven, stovetop

Spacious 9BR Home~Ideal for Groups~Near Downtown

10.0 out of 10, Exceptional, (1)
"Was a perfect location close to downtown and the Iowa Deer Classic! "
The price is HK$1,790
HK$5,301 total
includes taxes & fees
14 Jul - 15 Jul
Spacious 9BR Home~Ideal for Groups~Near Downtown
Downtown 2BD 2.5BA townhouse w/free garage parking
Interior

Downtown 2BD 2.5BA townhouse w/free garage parking

10.0 out of 10, Exceptional, (17)
"Easy, clean, and amazing location"
The price is HK$699
HK$1,882 total
includes taxes & fees
13 Jul - 14 Jul
Downtown 2BD 2.5BA townhouse w/free garage parking
Newly Remodeled Brick Home with wall Sculptures by the Airport
Fridge, microwave, oven, stovetop

Newly Remodeled Brick Home with wall Sculptures by the Airport

9.8 out of 10, Exceptional, (31)
"We came to Des Moines for a concert. Was so nice to drive a few minutes to a nice clean, quiet, spacious house to relax and spend the night. We would stay here again."
The price is HK$1,601
HK$2,303 total
includes taxes & fees
14 Jul - 15 Jul
Newly Remodeled Brick Home with wall Sculptures by the Airport
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Terrace/patio

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

10.0 out of 10, Exceptional, (58)
"We loved this super clean and cute house!"
The price is HK$1,213
HK$3,011 total
includes taxes & fees
4 Aug - 5 Aug
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Sleepover Brilliant 1BD/1BA + Gym - Des Moines
1 bedroom, iron/ironing board, free WiFi, bed sheets

Sleepover Brilliant 1BD/1BA + Gym - Des Moines

The price is HK$496
HK$1,479 total
includes taxes & fees
10 Jul - 11 Jul
Sleepover Brilliant 1BD/1BA + Gym - Des Moines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Can I find holiday rentals in Winterset?

Yes, there are holiday rentals close to the most popular sights in Winterset, or you can select a more secluded option if you're looking for a relaxing stay. Winterset is known for its shopping and restaurants. Make sure you have time to check out the bars while you're in the area.

What are some of the best holiday rentals that Winterset has to offer?

House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood : This holiday home rental outside of Winterset offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winterset?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Winterset stay.

What can I see and do in Winterset?

Cultural attractions include John Wayne Birthplace Museum and The Winterset Stage, whereas Pammel State Park is one spot to enjoy nature. While here, Madison County Courthouse and Roseman Bridge are other places worth a visit.

What are holiday rentals like in Winterset?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterset. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.