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

Winterset Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winterset vacation rentals

Outdoor dining

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 AED 461
AED 1,318 total
includes taxes & fees
31 Aug - 1 Sep
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Property grounds

2. 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, (413 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 AED 359
AED 632 total
includes taxes & fees
30 Aug - 31 Aug
Beautiful Rustic Barn just waiting for you to kick back and relax.
Exterior

3. 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)
"Spacious accommodations, clean, and excellent location in a quiet area. Host, Clayton, was very responsive. "
United States
John S.
The price is AED 380
AED 590 total
includes taxes & fees
28 Aug - 29 Aug
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
Bar (on property)

4. 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, (13 reviews)
"Great place to stay!"
United States
Elizabeth V.
The price is AED 480
AED 1,793 total
includes taxes & fees
2 Sep - 3 Sep
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
Smart TV, printers

5. 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 AED 347
AED 915 total
includes taxes & fees
1 Sep - 2 Sep
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
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 AED 344
AED 953 total
includes taxes & fees
28 Aug - 29 Aug
Top Floor, Modern & Upgraded with Pool Views
Coffee/tea maker, fridge, microwave, oven

7. 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 AED 496
AED 706 total
includes taxes & fees
31 Aug - 1 Sep
The Hen House Country Living with Farm Life Appeal Indianola, IA
TV

8. Sherman Hills Historic Retreat #6

Sherman Hills Historic Retreat #6
Downtown Des Moines
10.0 out of 10, Exceptional, (1 review)
"This small apartment was exactly what we needed for a quick trip to visit our son in Iowa, where he was interning for the summer. The location was excellent with convenient walking access to Smoky Row Coffee shop (coffee in the morning and ice cream at night....yum!). It was also right off the highway so zipping east to the Harvester Club where our son was working, or west into Des Moines to hit the Jordan Creek Mall was a breeze.Despite the record heat during the week we were there, the two...
United States
Rodney P.
The price is AED 158
AED 625 total
includes taxes & fees
30 Aug - 31 Aug
Sherman Hills Historic Retreat #6
Exterior

9. 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 AED 386
AED 617 total
includes taxes & fees
11 Sep - 12 Sep
Cozy pond house nestled in nature waiting for you to enjoy
Exterior

10. 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 AED 373
AED 965 total
includes taxes & fees
2 Sep - 3 Sep
Wooded Views | King Bed | No Stairs
Interior

11. Fun & Charming 1BR Apt near Drake

Fun & Charming 1BR Apt near Drake
Drake
8.0 out of 10, Very Good, (2 reviews)
"Abner is amazing. Communication was as smooth as can be, the place was left in great condition, and the house rules were respected. I hope to host them again in the future!"
United States
AbnerG
Fun & Charming 1BR Apt near Drake
Exterior

12. 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 AED 436
AED 743 total
includes taxes & fees
30 Aug - 31 Aug
Spacious Farmhouse beautifully decorated waiting for laughs and memories
Pool

13. 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 AED 431
AED 1,001 total
includes taxes & fees
1 Sep - 2 Sep
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
Interior

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (36 reviews)
"Very nice quiet place to stay. Beds were nice and comfy. Nice kitchen and laundry area.We enjoyed our stay"
United States
Doreen
The price is AED 514
AED 1,349 total
includes taxes & fees
1 Sep - 2 Sep
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Smart TV

15. Cozy #2 for YOU! 1-bed apartment in fantastic Sherman Hill Downtown Des Moines

Cozy #2 for YOU! 1-bed apartment in fantastic Sherman Hill Downtown Des Moines
Downtown Des Moines
9.2 out of 10, Wonderful, (11 reviews)
"The location is incredible, close to everything going on downtown or at Drake, and includes off-street parking! Check in is seamless and hosts are responsive! Perfect landing spot for a weekend in Des Moines with a great location and solid amenities!"
United States
Nathan S.
The price is AED 187
AED 650 total
includes taxes & fees
30 Aug - 31 Aug
Cozy #2 for YOU! 1-bed apartment in fantastic Sherman Hill Downtown Des Moines
Coffee/tea maker, fridge, microwave, oven

16. 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 AED 319
AED 795 total
includes taxes & fees
3 Sep - 4 Sep
Sleepover | Dashing 1BD/1BA - Des Moines
TV

17. Cozy Bungalow Retreat

Cozy Bungalow Retreat
Greater South Side
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay. Quiet and cozy"
United States
Christopher G.
The price is AED 413
AED 788 total
includes taxes & fees
29 Aug - 30 Aug
Cozy Bungalow Retreat
Exterior

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

Sleepover | Alluring 1BD/1BA - Des Moines
West Des Moines
The price is AED 279
AED 740 total
includes taxes & fees
30 Aug - 31 Aug
Sleepover | Alluring 1BD/1BA - Des Moines
Interior

19. Sleepover | Lovely 1BD/BA + High Ceilings - DSM

Sleepover | Lovely 1BD/BA + High Ceilings - DSM
West Des Moines
The price is AED 279
AED 740 total
includes taxes & fees
30 Aug - 31 Aug
Sleepover | Lovely 1BD/BA + High Ceilings - DSM
WiFi (free), bed sheets

20. Stylish and cozy studio near Western Gateway Park, combining comfort, convenience, and a prime Downtown location.

Stylish and cozy studio near Western Gateway Park, combining comfort, convenience, and a prime Downtown location.
Downtown Des Moines
10.0 out of 10, Exceptional, (6 reviews)
"Everything was clean"
United States
Shelby L.
The price is AED 166
AED 721 total
includes taxes & fees
30 Aug - 31 Aug
Stylish and cozy studio near Western Gateway Park, combining comfort, convenience, and a prime Downtown location.
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

10/10 Excellent
"The cleanliness of the everything overall. Especially the room. The staff was very friendly and helpful. Great customer service. Will definitely be booking there again!"
Dora 1-night trip
Posted 1 hour ago
Days Inn & Suites by Wyndham Des Moines Airport

Frequently asked questions

Can I find vacation rentals in Winterset?

Yes, you can find vacation rentals in Winterset close to Rotary Hedge Maze, or you can choose a secluded option if you want 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 vacation rentals in Winterset?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: Visitors like this Winterset vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winterset?

With 5 Expedia vacation rentals, you're sure 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 Roseman Bridge are other places worth a visit.

What are vacation rentals like in Winterset?

Vacation rentals are private properties you can stay in for several days or longer in Winterset. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.