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

Winterset Vacation Rentals

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Our top choices for Winterset vacation rentals

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, (414 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 ¥15,015
¥26,250 total
includes taxes & fees
Sep 13 - Sep 14
Beautiful Rustic Barn just waiting for you to kick back and relax.

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, (15 reviews)
"Spacious accommodations, clean, and excellent location in a quiet area. Host, Clayton, was very responsive. "
United States
John S.
The price is ¥15,899
¥23,314 total
includes taxes & fees
Sep 17 - Sep 18
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

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, (14 reviews)
"Great place to stay!"
United States
Elizabeth V.
The price is ¥20,092
¥71,536 total
includes taxes & fees
Sep 17 - Sep 18
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

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 ¥14,516
¥37,765 total
includes taxes & fees
Sep 13 - Sep 14
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts

5. Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines

Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines
Cumming
The price is ¥24,194
¥42,340 total
includes taxes & fees
Sep 15 - Sep 16
Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines

6. 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, (18 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is ¥20,737
¥29,193 total
includes taxes & fees
Sep 13 - Sep 14
The Hen House Country Living with Farm Life Appeal Indianola, IA

7. 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 ¥15,361
¥38,710 total
includes taxes & fees
Sep 13 - Sep 14
Top Floor, Modern & Upgraded with Open Balcony

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (37 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 ¥21,505
¥56,774 total
includes taxes & fees
Sep 14 - Sep 15
Spacious 4BR Home • WiFi • Family-Friendly • Waukee

9. 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 ¥18,241
¥30,766 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Farmhouse beautifully decorated waiting for laughs and memories

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

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.6 out of 10, Exceptional, (5 reviews)
"Very clean and really nice place. The host is professional and kind. I would definitely stay again."
United States
Mike
The price is ¥17,665
¥27,742 total
includes taxes & fees
Sep 13 - Sep 14
Cozy pond house nestled in nature waiting for you to enjoy

11. 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, (29 reviews)
"Great location very nice apartment "
United States
Cindy P.
The price is ¥17,512
¥39,226 total
includes taxes & fees
Oct 6 - Oct 7
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

12. 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 ¥26,882
¥74,303 total
includes taxes & fees
Sep 14 - Sep 15
Endless Fun! Family Home w/ Spacious Yard in Clive

13. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (28 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 ¥14,132
¥26,129 total
includes taxes & fees
Sep 22 - Sep 23
Farmhouse Oasis

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 ¥17,281
¥39,313 total
includes taxes & fees
Sep 15 - Sep 16
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

15. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (41 reviews)
"Very clean and spacious. Good location to downtown. Very comfortable home. Would recommend and would stay again!!"
United States
Melissa W.
The price is ¥15,346
¥38,349 total
includes taxes & fees
Sep 21 - Sep 22
Beautiful home minutes from downtown!

16. Sleepover | Charming 1BD/1BA - Downtown Des Moines

Sleepover | Charming 1BD/1BA - Downtown Des Moines
Woodland Heights
10.0 out of 10, Exceptional, (2 reviews)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
The price is ¥13,349
¥31,851 total
includes taxes & fees
Sep 13 - Sep 14
Sleepover | Charming 1BD/1BA - Downtown Des Moines

17. Sherman Hill Hide-a-way

Sherman Hill Hide-a-way
Downtown Des Moines
10.0 out of 10, Exceptional, (5 reviews)
"Good stay."
United States
Nick & Heather W.
The price is ¥8,280
¥27,682 total
includes taxes & fees
Oct 13 - Oct 14
Sherman Hill Hide-a-way

18. Sleepover | Extraordinary Studio + Gym- Des Moines

Sleepover | Extraordinary Studio + Gym- Des Moines
Drake
10.0 out of 10, Exceptional, (4 reviews)
"Nice place and close to where we needed to be. "
United States
Lori P.
The price is ¥11,659
¥30,622 total
includes taxes & fees
Oct 12 - Oct 13
Sleepover | Extraordinary Studio + Gym- Des Moines

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

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Woodland Heights
10.0 out of 10, Exceptional, (76 reviews)
"This was a charming house with space for our group of 6. Very clean throughout with comfortable beds. The location made getting around easy."
United States
Chris M.
The price is ¥19,936
¥53,812 total
includes taxes & fees
Oct 7 - Oct 8
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

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

Endless Fun! Family Home w/ Spacious Yard in Clive
Clive
9.6 out of 10, Exceptional, (4 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 ¥20,277
¥75,699 total
includes taxes & fees
Sep 14 - Sep 15
Endless Fun! Family Home w/ Spacious Yard in Clive
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:

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

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 Cedar 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.