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

Our top choices for Winterset vacation 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 ￥16,379
￥52,035 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥16,158
￥37,323 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥13,977
￥37,703 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥16,300
￥25,313 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥20,600
￥66,641 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥14,883
￥38,719 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥15,450
￥27,468 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥17,206
￥61,428 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥14,924
￥27,246 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥17,009
￥27,616 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥14,458
￥27,252 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥10,221
￥29,428 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥21,261
￥29,931 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥17,135
￥43,357 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥15,749
￥39,687 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥15,592
￥29,987 total
includes taxes & fees
Nov 4 - Nov 5
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 ￥16,158
￥39,440 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥13,686
￥33,714 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥20,474
￥35,807 total
includes taxes & fees
Oct 29 - Oct 30
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 ￥16,952
￥41,739 total
includes taxes & fees
Nov 2 - Nov 3
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

Hampton Inn Des Moines-Airport

Hampton Inn Des Moines-Airport

10/10 Excellent
"Stay-Park-Fly amenity is a good value."
Marlys 1-night trip
Posted 1 hour ago
Hampton Inn 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
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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.