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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winterset holiday rentals

A deck with a table and chairs, surrounded by a wooden deck and a white railing.

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

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Winterset
10.0 out of 10, Exceptional, (15 reviews)
"The house in Winterset was perfect in every way. It was beautifully furnished and extremely comfortable. We are so glad we stayed there."
United States
Nickay M.
The price is HK$801
HK$2,566 total
includes taxes & fees
2 Nov - 3 Nov
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A multi-story residential building with a stone facade, a small porch, and a garage.

2. The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym

The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
West Des Moines
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay! So much better than a hotel room!!"
United States
Janell R.
The price is HK$921
HK$2,007 total
includes taxes & fees
2 Nov - 3 Nov
The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
A residential complex with multiple apartment buildings, a swimming pool, and outdoor seating areas.

3. Luxe, First Floor Suite with Garage & Balcony

Luxe, First Floor Suite with Garage & Balcony
West Des Moines
10.0 out of 10, Exceptional, (1 review)
"Great quiet community, close to shopping and restaurants. A nice place to stay with great communication! Will most definitely stay here again in the future. "
United States
Amber T.
The price is HK$696
HK$1,878 total
includes taxes & fees
1 Nov - 2 Nov
Luxe, First Floor Suite with Garage & Balcony
A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

4. 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, (15 reviews)
"Beautiful place to stay and very accommodating host."
United States
Amy K.
The price is HK$812
HK$1,261 total
includes taxes & fees
1 Nov - 2 Nov
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

5. 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, (16 reviews)
"Great place to stay!"
United States
Elizabeth V.
The price is HK$1,026
HK$3,319 total
includes taxes & fees
9 Nov - 10 Nov
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

6. 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$1,946 total
includes taxes & fees
1 Nov - 2 Nov
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
A garden with a stream, rocks, and flowers.

7. 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, (415 reviews)
"This place was so incredibly cute. We loved our little getaway for our first anniversary and we had everything we needed and more. Thank you for providing such a great place, we’ll definitely be back!!"
United States
Genevieve P.
The price is HK$854
HK$1,457 total
includes taxes & fees
29 Oct - 30 Oct
Beautiful Rustic Barn just waiting for you to kick back and relax.
A modern kitchen with dark wooden cabinets, a stainless steel stove, and a granite countertop.

8. Adel 4BR/Game Room, Park Nearby & Sleeps 12

Adel 4BR/Game Room, Park Nearby & Sleeps 12
Adel
8.0 out of 10, Very good, (4 reviews)
"The house itself was beautiful. It was very clean and was decorated really cute. There were three bathrooms to go with the four bedrooms, so everyone had their own private space which was really nice. House was in a nice, quiet neighborhood. Would definitely stay here again if we are in the area."
United States
Darla F.
The price is HK$1,169
HK$3,453 total
includes taxes & fees
9 Nov - 10 Nov
Adel 4BR/Game Room, Park Nearby & Sleeps 12
A single-story house with a front yard, a mailbox, and a tree.

9. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (32 reviews)
"The property was great and would stay again and recommend to family and friends if ciming into town."
United States
Michael D.
The price is HK$751
HK$1,365 total
includes taxes & fees
2 Nov - 3 Nov
Farmhouse Oasis
A house by a lake with a covered porch and a satellite dish.

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

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.8 out of 10, Exceptional, (6 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$847
HK$1,376 total
includes taxes & fees
29 Oct - 30 Oct
Cozy pond house nestled in nature waiting for you to enjoy
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

11. 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, (21 reviews)
"Very nice place to stay."
United States
Todd W.
The price is HK$763
HK$1,402 total
includes taxes & fees
29 Oct - 30 Oct
Spacious Farmhouse beautifully decorated waiting for laughs and memories
An outdoor patio with a fire pit, seating, and a grill area.

12. Sleepover | Lavish Studio and Gym - Des Moines

Sleepover | Lavish Studio and Gym - Des Moines
Drake
6.8 out of 10, (3 reviews)
"Everything was just as described. I would definitely stay here again. The location is perfect for visiting the campus. "
United States
Don B.
The price is HK$423
HK$1,368 total
includes taxes & fees
29 Oct - 30 Oct
Sleepover | Lavish Studio and Gym - Des Moines
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

13. 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, (19 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is HK$1,059
HK$1,491 total
includes taxes & fees
8 Nov - 9 Nov
The Hen House Country Living with Farm Life Appeal Indianola, IA
A modern building with a reflective pool in front.

14. 1st Floor, Stylish & Upgraded Retreat with Garage

1st Floor, Stylish & Upgraded Retreat with Garage
West Des Moines
9.6 out of 10, Exceptional, (22 reviews)
"Modern new and like a bedroom suite at a hotel but cheaper."
United States
Jon C.
The price is HK$853
HK$2,177 total
includes taxes & fees
1 Nov - 2 Nov
1st Floor, Stylish & Upgraded Retreat with Garage
A modern building with a reflective pool in front.

15. Top Floor, Modern & Upgraded with Open Balcony

Top Floor, Modern & Upgraded with Open Balcony
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$785
HK$1,995 total
includes taxes & fees
1 Nov - 2 Nov
Top Floor, Modern & Upgraded with Open Balcony
A staircase with white railings and a potted plant at the bottom.

16. 2-bedroom apartment close to uptown Creston with WiFi and off street parking.

2-bedroom apartment close to uptown Creston with WiFi and off street parking.
Creston
10.0 out of 10, Exceptional, (10 reviews)
"Great little apartment-like spot for stays on Creston. Easy checkin, clean spot, easy checkout."
United States
Samuel
The price is HK$777
HK$1,494 total
includes taxes & fees
4 Nov - 5 Nov
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
A swimming pool with lounge chairs, a covered seating area, and a multi-story building with balconies.

17. 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, (31 reviews)
"This VRBO is located in a safe, clean area. The unit itself was clean and comfortable, Everything was as described and communication was great. It was nice to have a private garage. Definitely would stay there again."
United States
Colleen N.
The price is HK$885
HK$2,063 total
includes taxes & fees
17 Nov - 18 Nov
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
A modern kitchen with grey cabinets, stainless steel appliances, and a wooden dining table.

18. Sleepover | Dashing 1BD/1BA - Des Moines

Sleepover | Dashing 1BD/1BA - Des Moines
West Des Moines
9.0 out of 10, Wonderful, (2 reviews)
"Good location near shops and highway."
United States
Liliam W.
The price is HK$682
HK$1,679 total
includes taxes & fees
1 Nov - 2 Nov
Sleepover | Dashing 1BD/1BA - Des Moines
A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

19. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (11 reviews)
"We absolutely loved our stay. The place was clean and comfortable. Very peaceful and quiet."
United States
Ana M.
The price is HK$1,020
HK$1,784 total
includes taxes & fees
29 Oct - 30 Oct
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A modern living room with a grey sectional sofa, a small white table, and a large round rug. There are two windows with floral curtains, a wooden door, and a white ceiling.

20. Beautiful 3-bedroom house with AC in adorable Des Moines

Beautiful 3-bedroom house with AC in adorable Des Moines
Beaverdale
9.6 out of 10, Exceptional, (23 reviews)
"Perfect for our needs. The host was very communicative during our stay and check-in and check-out was simple and smooth. Great value and we would stay here again!"
United States
Michael G.
The price is HK$844
HK$2,079 total
includes taxes & fees
2 Nov - 3 Nov
Beautiful 3-bedroom house with AC in adorable 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.
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Top Winterset Hotel Reviews

Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

8/10 Good
"Very good for a budget motel. The breakfast food quality was very poor, including what may have been the worst eggs I ever had."
Marlin 1-night trip
Posted 3 hours ago
Days Inn & Suites by Wyndham Des Moines Airport

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?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: This holiday home rental outside of Winterset offers a fireplace, a patio 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. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winterset?

With 5 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, Clark Tower and Cedar 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.