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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
$291 nightly
The price is $326
Oct 20 - Oct 21
Total with taxes and fees
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
9.8 out of 10, Exceptional, (30 reviews)
"Very nice property. Owners were prompt with responses to questions. Would def book again!"
United States
Elizabeth F.
$209 nightly
The price is $234
Oct 7 - Oct 8
Total with taxes and fees
The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
A house with a swimming pool, a covered patio, and a stone chimney.

3. Wooded Views | King Bed | No Stairs

Wooded Views | King Bed | No Stairs
West Des Moines
10.0 out of 10, Exceptional, (2 reviews)
"Great quiet place to stay. Very clean."
United States
Emily R.
$221 nightly
The price is $247
Oct 7 - Oct 8
Total with taxes and fees
Wooded Views | King Bed | No Stairs
A modern building with a reflective pool in front.

4. 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.
$246 nightly
The price is $275
Oct 7 - Oct 8
Total with taxes and fees
1st Floor, Stylish & Upgraded Retreat with Garage
A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

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.
$220 nightly
The price is $246
Oct 7 - Oct 8
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

6. 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.
$436 nightly
The price is $488
Oct 13 - Oct 14
Total with taxes and fees
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

7. 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.
$155 nightly
The price is $174
Nov 1 - Nov 2
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A garden with a stream, rocks, and flowers.

8. 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.
$201 nightly
The price is $211
Oct 7 - Oct 8
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
A house by a lake with a covered porch and a satellite dish.

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

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and really nice place. The host is professional and kind. I would definitely stay again."
United States
Mike
$181 nightly
The price is $190
Oct 7 - Oct 8
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

10. 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.
$181 nightly
The price is $190
Oct 7 - Oct 8
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
A single-story house with a front yard, a mailbox, and a tree.

11. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (30 reviews)
"The property was great and would stay again and recommend to family and friends if ciming into town."
United States
Michael D.
$168 nightly
The price is $176
Oct 14 - Oct 15
Total with taxes and fees
Farmhouse Oasis
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

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.
$218 nightly
The price is $229
Oct 7 - Oct 8
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A room with white walls, a concrete floor, and a ceiling with exposed beams and a single light fixture.

13. 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.
$215 nightly
The price is $241
Oct 14 - Oct 15
Total with taxes and fees
Luxe, First Floor Suite with Garage & Balcony
A swimming pool with lounge chairs, a covered seating area, and a multi-story building with balconies.

14. 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, (30 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.
$237 nightly
The price is $266
Oct 27 - Oct 28
Total with taxes and fees
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
A staircase with white railings and a potted plant at the bottom.

15. 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
$169 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

16. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (11 reviews)
"Nice place"
United States
Dale T.
$203 nightly
The price is $227
Oct 7 - Oct 8
Total with taxes and fees
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A modern building with a reflective pool in front.

17. 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.
$225 nightly
The price is $252
Oct 12 - Oct 13
Total with taxes and fees
Top Floor, Modern & Upgraded with Open Balcony
An outdoor patio with a fire pit, seating, and a grill area.

18. Sleepover | Attractive Studio and Gym - Des Moines

Sleepover | Attractive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (3 reviews)
"Very convenient place to stay for the Drake Relays. Would definitely look to stay there again."
United States
Josh
$161 nightly
The price is $196
Oct 7 - Oct 8
Total with taxes and fees
Sleepover | Attractive Studio and Gym - Des Moines
A multi-story building with a flat roof, large windows, and a sign reading 'KEYSTONE'.

19. Sleepover | Marvelous 1BD/1BA - Des Moines

Sleepover | Marvelous 1BD/1BA - Des Moines
West Des Moines
9.2 out of 10, Wonderful, (5 reviews)
"We stayed at the Flux apartments in downtown. Our accommodation was exceptional in all respects. Thank you for your hospitality!"
United States
Miriam G.
$189 nightly
The price is $214
Oct 7 - Oct 8
Total with taxes and fees
Sleepover | Marvelous 1BD/1BA - Des Moines
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, (21 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.
$229 nightly
The price is $257
Oct 14 - Oct 15
Total with taxes and fees
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

Drury Inn & Suites West Des Moines

Drury Inn & Suites West Des Moines

10/10 Excellent
"We love this hotel chain."
John Kevin 4-night trip
Posted less than an hour ago
Drury Inn & Suites West Des Moines

Find out more about Winterset

Everything you need to know about Winterset vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winterset vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winterset vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterset. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winterset in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $234 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winterset rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winterset vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterset. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.