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Winterset Holiday Rentals

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Holiday Rentals in Winterset

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

The price is NZ$564
includes taxes & fees
15 July - 16 July
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

• 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 NZ$379
includes taxes & fees
1 July - 2 July
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

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

10.0 out of 10, Exceptional, (30)
"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 NZ$907
includes taxes & fees
13 July - 14 July
Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

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

10.0 out of 10, Exceptional, (3)
"Thank you Lori for allowing us to stay in your beautiful home.We found every thing exceeded our expectations. All the little extra items you provided made us feel like home and if we had forgotten something, you had it there. "
The price is NZ$312
includes taxes & fees
30 June - 1 July
The Hen House Country Living with Farm Life Appeal Indianola, IA

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 NZ$453
includes taxes & fees
30 June - 1 July
Beautiful home minutes from downtown!

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 NZ$519
includes taxes & fees
30 June - 1 July
Spacious updated home minutes from Airport and DT!

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...
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!

10.0 out of 10, Exceptional, (15)
"Everything was great!"
The price is NZ$342
includes taxes & fees
7 July - 8 July
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!

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 NZ$348
includes taxes & fees
13 July - 14 July
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

The price is NZ$348
includes taxes & fees
13 July - 14 July
The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM

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 NZ$381
includes taxes & fees
1 July - 2 July
The Kirkwood - Cozy 2bdrm Oasis

The Cozy Cottage - Entire house in Des Moines

9.6 out of 10, Exceptional, (4)
"It was perfect for our needs !"
The price is NZ$344
includes taxes & fees
30 June - 1 July
The Cozy Cottage - Entire house in Des Moines

Downtown Skyline Views in Modern Townhome with Rooftop Patios

10.0 out of 10, Exceptional, (27)
"We had a great time and an easy stay walking distance from several great spots."
The price is NZ$503
includes taxes & fees
1 July - 2 July
Downtown Skyline Views in Modern Townhome with Rooftop Patios

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

2.0 star property
8.8 out of 10, Excellent, (21)
"Wonderful property and host! "
The price is NZ$592
includes taxes & fees
7 July - 8 July
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

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

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

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! "
Spacious 9BR Home~Ideal for Groups~Near Downtown

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

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

Downtown 2BD 2.5BA townhouse w/free garage parking

10.0 out of 10, Exceptional, (17)
"Easy, clean, and amazing location"
The price is NZ$389
includes taxes & fees
6 July - 7 July
Downtown 2BD 2.5BA townhouse w/free garage parking

Newly Remodeled Brick Home with wall Sculptures by the Airport

9.8 out of 10, Exceptional, (30)
"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 NZ$523
includes taxes & fees
13 July - 14 July
Newly Remodeled Brick Home with wall Sculptures by the Airport

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

10.0 out of 10, Exceptional, (57)
"We loved this super clean and cute house!"
The price is NZ$609
includes taxes & fees
2 July - 3 July
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
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.
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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?

Newly remodeled 3-bedroom ranch with pool table, patio, and grill in Urbandale.: This holiday home rental outside of Winterset has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.