Winterset Holiday Rentals from €244: 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

30 Nov - 1 Dec

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cumming

Elizabeth V.

A multi-story residential building with a stone facade, a small porch, and a garage.

3. The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym

West Des Moines

Janell R.

includes taxes & fees

9 Dec - 10 Dec

A modern building with a reflective pool in front.

4. No Stairs! Upgraded Executive Suite with Garage

West Des Moines

Jon C.

A garden with a stream, rocks, and flowers.

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

NEW VIRGINIA

Genevieve P.

includes taxes & fees

13 Nov - 14 Nov

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

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

Indianola

Adam b.

includes taxes & fees

10 Nov - 11 Nov

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

West Des Moines

Amy K.

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

Lisa R.

includes taxes & fees

11 Nov - 12 Nov

A spacious living room with a sofa, a dining table, and a large window offering a view of the outdoors.

9. Modern Luxury West Des Moines Condo

West Des Moines

Melissa H.

includes taxes & fees

7 Dec - 8 Dec

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

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

Waukee

Steven B.

includes taxes & fees

21 Nov - 22 Nov

A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

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

Waukee

Amy P.

includes taxes & fees

13 Nov - 14 Nov

A house with a swimming pool, a covered patio, and a stone chimney.

12. Wooded Views | King Bed | No Stairs

West Des Moines

Emily R.

A modern kitchen with stainless steel appliances, dark cabinetry, and a granite countertop.

13. LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

Waukee

Jenny B.

includes taxes & fees

10 Nov - 11 Nov

A two-story residential building with a front porch, a street lamp, and a well-maintained lawn.

14. 3-bedroom End-Unit Townhome in beautiful West Des Moines

West Des Moines

A spacious kitchen with white cabinetry, a granite countertop, and a large island.

15. AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

West Des Moines

Cindy H.

includes taxes & fees

8 Dec - 9 Dec

A modern house with a stone pillar, a front door with a glass panel, a bench, and a small garden.

16. Convenient functional quiet 5 bedroom 3 bath home in Clive.

Clive

Anonymous traveller

A dining room with a wooden table, chairs, a bench, a chandelier, and a potted plant.

17. •Delightful 5b stay in Paradise!!•

Waukee

justine p.

includes taxes & fees

22 Nov - 23 Nov

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

18. Spacious Farmhouse beautifully decorated waiting for laughs and memories

New Virginia

Todd W.

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a central island.

19. Peaceful Modern Studio in Prime Location

Waukee

includes taxes & fees

10 Nov - 11 Nov

A residential complex with multiple apartment buildings, a swimming pool, and outdoor seating areas.

20. Luxe Executive Suite with Attached, Private Garage

West Des Moines

Amber T.

includes taxes & fees

10 Nov - 11 Nov

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Top Winterset Hotel Reviews

Hotel Fort Des Moines, Curio Collection by Hilton

10/10 Excellent

"Try and stay here every time I visit Des Moines. Love the location, walkable to so many great restaurants, bars and things to do. It’s always clean. Staff are always so friendly and accommodating. Highly recommend this hotel!"

Sleep Inn & Suites West Des Moines near Jordan Creek

8/10 Good

"Had a late check-in for an overnight stay due to a family funeral the next morning. We were very glad to see the room was as clean as other reviews stated. Parts of the tub and toilet showed rust and wear, but everything worked for what we needed. Breakfast was well displayed and offered a good variety. We were able to drop off keys for an easy check out."

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, apart-hotels, 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 favorite 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 depends 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 €244 per night. Entering your travel dates in the search wizard you might find 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 Cedar 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. Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

3. The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym

4. No Stairs! Upgraded Executive Suite with Garage

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

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

7. 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU