A red covered bridge over a calm river, surrounded by lush greenery and trees.

Winterset Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winterset holiday rentals

Property grounds

1. Beautiful Rustic Barn just waiting for you to kick back and relax.

Beautiful Rustic Barn just waiting for you to kick back and relax.
NEW VIRGINIA
10.0 out of 10, Exceptional, (411 reviews)
"The barn and grounds are immaculate. This place is enchanting. Stay here. You will not be disappointed. "
United States
Barbara O.
The price is HK$767
HK$1,340 total
includes taxes & fees
9 Aug - 10 Aug
Beautiful Rustic Barn just waiting for you to kick back and relax.
Exterior

2. 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
West Des Moines
9.2 out of 10, Wonderful, (12 reviews)
"Spacious accommodations, clean, and excellent location in a quiet area. Host, Clayton, was very responsive. "
United States
John S.
The price is HK$812
HK$1,392 total
includes taxes & fees
12 Aug - 13 Aug
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
Bar (on property)

3. Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
Cumming
10.0 out of 10, Exceptional, (12 reviews)
"Great place to stay!"
United States
Elizabeth V.
The price is HK$1,149
HK$3,984 total
includes taxes & fees
25 Aug - 26 Aug
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
Smart TV, printers

4. Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Waukee
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location, very clean, would definitely stay again! "
United States
Amy P.
The price is HK$741
HK$1,928 total
includes taxes & fees
9 Aug - 10 Aug
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Pool

5. The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
West Des Moines
9.8 out of 10, Exceptional, (28 reviews)
"Great location very nice apartment "
United States
Cindy P.
The price is HK$999
HK$2,182 total
includes taxes & fees
3 Sept - 4 Sept
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
Exterior

6. Top Floor, Modern & Upgraded with Pool Views

Top Floor, Modern & Upgraded with Pool Views
West Des Moines
8.0 out of 10, Very good, (4 reviews)
"We were here to help our daughter move. The apartment is in the same complex which was very helpful. There is plenty to do if here for vacation. The two state parks we went to were fairly close and nice. There are many stores, a mall, and plenty of restaurants within a ten minute drive. Des Moines is 20-30 minutes."
United States
H and P H.
The price is HK$885
HK$2,229 total
includes taxes & fees
11 Aug - 12 Aug
Top Floor, Modern & Upgraded with Pool Views
Interior

7. Endless Fun! Family Home w/ Spacious Yard in Clive

Endless Fun! Family Home w/ Spacious Yard in Clive
3.0 star property
Clive
The price is HK$1,365
HK$3,785 total
includes taxes & fees
31 Aug - 1 Sept
Endless Fun! Family Home w/ Spacious Yard in Clive
Coffee/tea maker, fridge, microwave, oven

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

The Hen House Country Living with Farm Life Appeal Indianola, IA
Indianola
10.0 out of 10, Exceptional, (17 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is HK$1,059
HK$1,482 total
includes taxes & fees
2 Sept - 3 Sept
The Hen House Country Living with Farm Life Appeal Indianola, IA
Exterior

9. Wooded Views | King Bed | No Stairs

Wooded Views | King Bed | No Stairs
West Des Moines
10.0 out of 10, Exceptional, (1 review)
"Great quiet place to stay. Very clean."
United States
Emily R.
The price is HK$982
HK$2,295 total
includes taxes & fees
11 Aug - 12 Aug
Wooded Views | King Bed | No Stairs
Exterior

10. Spacious Farmhouse beautifully decorated waiting for laughs and memories

Spacious Farmhouse beautifully decorated waiting for laughs and memories
New Virginia
10.0 out of 10, Exceptional, (19 reviews)
"A perfect place to relax! This farmhouse was spotless and had everything we needed for a long, comfortable weekend. Lots of seating, comfy beds and bedding, fluffy towels and peaceful surroundings. We loved it here! The last time we were here, we stayed in their barn vrbo, which was also a great place!"
United States
Chris M.
The price is HK$931
HK$1,571 total
includes taxes & fees
6 Aug - 7 Aug
Spacious Farmhouse beautifully decorated waiting for laughs and memories
Interior

11. Spacious 4BR Home • WiFi • Family-Friendly • Waukee

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (34 reviews)
"This is a great house in a great location. We had a group of 8 adults that stayed here and it accommodated us very well! I would definitely stay here again."
United States
Lisa J.
The price is HK$1,223
HK$3,074 total
includes taxes & fees
11 Aug - 12 Aug
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Property grounds

12. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (27 reviews)
"This was a beautiful rural setting. We enjoyed our stay very much. "
United States
Norman Z.
The price is HK$822
HK$1,440 total
includes taxes & fees
18 Aug - 19 Aug
Farmhouse Oasis
Dining

13. Beach Access/Kid Friendly/Park/Office/4BR/2B

Beach Access/Kid Friendly/Park/Office/4BR/2B
Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"Great house, very comfortable, lots of room had everything we could have needed "
United States
Spencer B.
Beach Access/Kid Friendly/Park/Office/4BR/2B
Smart TV

14. • Lively Cottage 2 King Beds 4 Bed 2 Bath •

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Indianola
9.4 out of 10, Exceptional, (23 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is HK$882
HK$2,025 total
includes taxes & fees
11 Aug - 12 Aug
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Coffee/tea maker, fridge, microwave, oven

15. Upscale New Studio in Waukee

Upscale New Studio in Waukee
Waukee
Upscale New Studio in Waukee
Exterior

16. Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.6 out of 10, Exceptional, (4 reviews)
"It was more than we expected, a perfect place to get away for some peace and quiet. Super clean and very well equipped with everything we needed. Can't wait to stay again!"
United States
Eric F.
The price is HK$823
HK$1,317 total
includes taxes & fees
20 Aug - 21 Aug
Cozy pond house nestled in nature waiting for you to enjoy
Exterior

17. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (39 reviews)
"What a great place to stay! "
United States
Annie P.
The price is HK$918
HK$2,143 total
includes taxes & fees
10 Aug - 11 Aug
Beautiful home minutes from downtown!
Exterior

18. Endless Fun! Family Home w/ Spacious Yard in Clive

Endless Fun! Family Home w/ Spacious Yard in Clive
Clive
9.4 out of 10, Exceptional, (3 reviews)
"There were 6 of us here to bicycle the Raccoon River valley trail and the property was very close to the trail. We all slept well, loved sitting in the back yard and gathering inside. It was the perfect haven each evening. We had plenty of room and really loved the house."
United States
delores C.
The price is HK$1,169
HK$4,058 total
includes taxes & fees
12 Aug - 13 Aug
Endless Fun! Family Home w/ Spacious Yard in Clive
Smart TV

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

The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
Des Moines
The price is HK$823
HK$1,713 total
includes taxes & fees
10 Aug - 11 Aug
The Cactus House: A Boho Western Single Family Home Just South of Downtown DSM
Dining

20. Free Breakfast, Indoor Pool, Hot Tub | King Studio

Free Breakfast, Indoor Pool, Hot Tub | King Studio
West Des Moines
The price is HK$748
HK$1,014 total
includes taxes & fees
23 Aug - 24 Aug
Free Breakfast, Indoor Pool, Hot Tub | King Studio
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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Top Winterset Hotel Reviews

Find out more about Winterset

Search for holiday rentals in Winterset on Expedia! You can easily find your home rentals, villas, holiday apartments in Winterset using one of the methods below:

  • View our selection of featured holiday rentals in Winterset
  • Use the map to find apartments and other holiday homes in the Winterset neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winterset while they last

Look no further and take a look at our great range of rental properties in Winterset!

Frequently asked questions

Can I find holiday rentals in Winterset?

Yes, there are holiday rentals in Winterset close to Rotary Hedge Maze, 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?

Heated Pool Hot Tub PicklebalMovieTheaterPoolTable GameR Golf: This holiday home rental outside of Winterset offers an outdoor pool, a fireplace and a BBQ 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. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Winterset?

With 6 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, Cedar Bridge 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.