Winterset Holiday Rentals from AU$226: Search Short-Term Rentals

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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

Winterset

Nickay M.

includes taxes & fees

8 Sept - 9 Sept

A garden with a stream, rocks, and flowers.

2. Beautiful Rustic Barn just waiting for you to kick back and relax.

NEW VIRGINIA

Genevieve P.

includes taxes & fees

8 Sept - 9 Sept

A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

3. 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

West Des Moines

John S.

includes taxes & fees

8 Sept - 9 Sept

4. Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

Cumming

Elizabeth V.

includes taxes & fees

10 Sept - 11 Sept

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

Waukee

Amy P.

includes taxes & fees

13 Sept - 14 Sept

A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

6. Spacious Farmhouse beautifully decorated waiting for laughs and memories

New Virginia

Todd W.

includes taxes & fees

8 Sept - 9 Sept

A kitchen with wooden cabinets, a stove, and various kitchen appliances.

7. The Hen House Country Living with Farm Life Appeal Indianola, IA

Indianola

Adam b.

includes taxes & fees

11 Sept - 12 Sept

A modern kitchen with a dining area, wooden flooring, and a large window offering a view of the backyard.

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

Waukee

Doreen

includes taxes & fees

8 Sept - 9 Sept

An outdoor patio with a fire pit, seating, and a grill area.

9. Sleepover | Impressive Studio and Gym - Des Moines

Drake

Gerardo

includes taxes & fees

8 Sept - 9 Sept

A spacious living area with a red sofa, wooden flooring, a flat-screen TV, and a large window with blinds.

10. • Lively Cottage 2 King Beds 4 Bed 2 Bath •

Indianola

Spring A.

includes taxes & fees

8 Sept - 9 Sept

11. Sleepover | Extraordinary Studio + Gym- Des Moines

Drake

Lori P.

includes taxes & fees

8 Sept - 9 Sept

A living room with a sofa, a coffee table, a TV, a ceiling fan, and a window with blinds.

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

Downtown Des Moines

Nathan S.

includes taxes & fees

9 Sept - 10 Sept

A single-story house with a front yard, a mailbox, and a tree.

13. Farmhouse Oasis

Dallas Center

Michael D.

includes taxes & fees

21 Sept - 22 Sept

A residential neighborhood with a house featuring a stone foundation, a sloped roof, and a front yard with a tree and a small garden.

14. Beautiful home minutes from downtown!

Des Moines

Melissa W.

includes taxes & fees

8 Sept - 9 Sept

A house by a lake with a covered porch and a satellite dish.

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

Osceola

Mike

includes taxes & fees

11 Sept - 12 Sept

A swimming pool with lounge chairs, a covered seating area, and a multi-story building with balconies.

16. The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

West Des Moines

Cindy P.

includes taxes & fees

4 Oct - 5 Oct

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

West Des Moines

includes taxes & fees

8 Sept - 9 Sept

A modern kitchen with a built-in microwave, stove, and stainless steel refrigerator.

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

Cumming

includes taxes & fees

28 Sept - 29 Sept

A multi-story building with a flat roof, large windows, and a sign reading 'KEYSTONE'.

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

West Des Moines

includes taxes & fees

8 Sept - 9 Sept

A living room with a ceiling fan, a TV, a sofa, and a coffee table.

20. Sherman Hills Historic Retreat #6

Downtown Des Moines

"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...

Rodney P.

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Top Winterset Hotel Reviews

Cobblestone Inn & Suites - Winterset, IA

10/10 Excellent

"Great hotel - no elevator, but no problem for us!"

SpringHill Suites Des Moines West

8/10 Good

"Front desk gentleman was very helpful and hospitable. Hotel room was mostly clean, though we did have a one of the comforters that appeared dirty— but front desk gave us a fresh one with no issues. Only real complaint was the breakfast— the breakfast room is way too small for the amount of people that showed for breakfast (830am) at the time we were there. We had to stand and eat and most of the food choices were gone when we arrived (breakfast crew was doing their best to keep up, but seemed understaffed maybe or maybe just not enough options available?). We let the kids eat and then the adults went elsewhere for food because of the lack of food available. All-in-all it was still a nice stay and we would return and recommend, just try to get to breakfast first thing instead."

Hampton Inn Des Moines-Airport

8/10 Good

"Michelle at the front desk was AMAZING. Give that gal a raise! Comfy beds. Nice breakfast. Our room was humid but located across from ice machine and laundry on 3rd floor so perhaps that contributed. Nice stay ceey close to the airport after a long day of flying and appreciated the 1/2 mile proximity!"

AmericInn by Wyndham Des Moines Airport

8/10 Good

"Our room was on the second floor; I’m grateful that my bag was light since no elevator required me to carry it up stairs. This will be good to know if you’re traveling with heavy bags. Breakfast was nice; there was something for everyone from waffles to eggs and sausage with biscuits and gravy."

Find out more about Winterset

Everything you need to know about Winterset holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winterset holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterset holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterset holiday rentals we have selected for you start as low as AU$226 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset holiday 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 holiday.

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.

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 Roseman 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.

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Check prices for these dates

Our top choices for Winterset holiday rentals

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

2. Beautiful Rustic Barn just waiting for you to kick back and relax.

3. 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

4. Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

5. Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts

6. Spacious Farmhouse beautifully decorated waiting for laughs and memories

7. The Hen House Country Living with Farm Life Appeal Indianola, IA

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

9. Sleepover | Impressive Studio and Gym - Des Moines

10. • Lively Cottage 2 King Beds 4 Bed 2 Bath •

11. Sleepover | Extraordinary Studio + Gym- Des Moines

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

13. Farmhouse Oasis

14. Beautiful home minutes from downtown!

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

16. The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

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

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

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

20. Sherman Hills Historic Retreat #6

Find holiday rentals that suit your style

Top Winterset Hotel Reviews

Cobblestone Inn & Suites - Winterset, IA

Home2 Suites by Hilton Des Moines at Drake University

SpringHill Suites Des Moines West

Hampton Inn Des Moines-Airport

Wildwood Lodge

Super 8 by Wyndham Clive IA

Holiday Inn Des Moines-Airport/Conf Center by IHG

Days Inn & Suites by Wyndham Des Moines Airport

AmericInn by Wyndham Des Moines Airport

Find out more about Winterset

Frequently asked questions

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