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Holiday Rentals in Winterset

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Our top choices for Winterset holiday rentals

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, (5)
"We had everything we could possibly need for our stay, a well equipped kitchen, great gathering areas, comfy beds, games, and being centrally located to the things we wanted to see. Our home was nicely decorated and spotlessly clean"
United States
Debbie M.
The price is €310
includes taxes & fees
4 Jan - 5 Jan 2026
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Quiet Studio on Grand Ave - Heart of Downtown

Quiet Studio on Grand Ave - Heart of Downtown
Downtown Des Moines
9.4 out of 10, Exceptional, (6)
"Property was in a good location, street parking was very easy. Host was incredibly responsive and helpful. "
United States
Cameron W.
The price is €839
includes taxes & fees
23 Dec - 24 Dec
Quiet Studio on Grand Ave - Heart of Downtown

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
2.0 star property
Woodland Heights
10.0 out of 10, Exceptional, (2)
"Cozy, had everything we needed, convenient "
United States
Jordan S.
The price is €195
includes taxes & fees
29 Dec - 30 Dec
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Sleepover: Impressive Studio and Gym - Des Moines

Sleepover: Impressive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (2)
"The place was located right next door to Drake which made doing a campus visit easily walkable and so were restaurants. Found parking on the street nearby and didn’t have to move the car until checkout. "
United States
Thomas
The price is €155
includes taxes & fees
23 Dec - 24 Dec
Sleepover: Impressive Studio and Gym - Des Moines

Sleepover: Attractive Studio and Gym - Des Moines

Sleepover: Attractive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (2)
"Clean and quiet for our stay. "
United States
Jackie
The price is €155
includes taxes & fees
23 Dec - 24 Dec
Sleepover: Attractive Studio and Gym - Des Moines

Valley Junction Getaway

Valley Junction Getaway
West Des Moines
10.0 out of 10, Exceptional, (1)
"Great place to stay for a night. Everything was clean and neat. "
United States
Nicole C.
The price is €107
includes taxes & fees
31 Dec - 1 Jan 2026
Valley Junction Getaway

Sleepover: Charming 1BD/1BA - Downtown Des Moines

Sleepover: Charming 1BD/1BA - Downtown Des Moines
Woodland Heights
10.0 out of 10, Exceptional, (1)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
Sleepover: Charming 1BD/1BA - Downtown Des Moines

Historic Valley Junction Loft

Historic Valley Junction Loft
West Des Moines
9.8 out of 10, Exceptional, (21)
"Great location, clean and comfy place. The location is charming, with a number of shops and restaurants next door. Would definitely stay here again. "
United States
Rebecca S.
The price is €122
includes taxes & fees
26 Dec - 27 Dec
Historic Valley Junction Loft

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, (8)
"Our host was amazing. Went above to make sure we had a great stay. Very personable..We both enjoyed visiting with her and learning more about the area. We will definitely return to the Hen House"
United States
Madonna
The price is €165
includes taxes & fees
4 Jan - 5 Jan 2026
The Hen House Country Living with Farm Life Appeal Indianola, IA

• 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, (18)
"Had a great stay, will come back!"
United States
Spring A.
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

2BR 2 BA Apt Downtown w/Hot Tub & Amenities!

2BR 2 BA Apt Downtown w/Hot Tub & Amenities!
Downtown Des Moines
9.0 out of 10, Wonderful, (4)
"Very Clean. Perfect downtown location. The number of walkable restaurants were outstanding. Highly recommend brunch at Americana and dinner at Exile. "
United States
Jeanne C.
The price is €1,371
includes taxes & fees
23 Dec - 24 Dec
2BR 2 BA Apt Downtown w/Hot Tub & Amenities!

Nice 2 bedroom in Sherman Hill-8

Nice 2 bedroom in Sherman Hill-8
Downtown Des Moines
9.2 out of 10, Wonderful, (21)
"Nice location "
United States
Allen E.
The price is €167
includes taxes & fees
28 Dec - 29 Dec
Nice 2 bedroom in Sherman Hill-8

Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.6 out of 10, Exceptional, (26)
"Clean house, comfortable beds, quiet neighborhood, good location "
United States
William S.
The price is €242
includes taxes & fees
23 Dec - 24 Dec
Beautiful home minutes from downtown!

Beautiful 2BR N of Grand near Downtown

Beautiful 2BR N of Grand near Downtown
North of Grand
8.0 out of 10, Very good, (2)
"Great place, clean, organized, well maintained and the hosts have made it a comfortable cozy welcoming space. So well stocked with everything you need to make it easy to be away from home. Great location."
United States
Michael B.
Beautiful 2BR N of Grand near Downtown

West Des Moines- Garage, Gym, Pool, Jordan Creek

West Des Moines- Garage, Gym, Pool, Jordan Creek
West Des Moines
9.6 out of 10, Exceptional, (11)
"Just as advertise prompt response from host clean and apt was as advertised!! Great stay"
United States
Raul N.
The price is €169
includes taxes & fees
23 Dec - 24 Dec
West Des Moines- Garage, Gym, Pool, Jordan Creek

Fun & Charming 1BR Apt near Drake

Fun & Charming 1BR Apt near Drake
Drake
8.0 out of 10, Very good, (2)
"Abner is amazing. Communication was as smooth as can be, the place was left in great condition, and the house rules were respected. I hope to host them again in the future!"
United States
AbnerG
Fun & Charming 1BR Apt near Drake

Cozy apartment with nice view-9

Cozy apartment with nice view-9
Downtown Des Moines
9.0 out of 10, Wonderful, (19)
"I only stayed over night but it was very clean and cute. "
United States
Kailyn C.
The price is €149
includes taxes & fees
28 Dec - 29 Dec
Cozy apartment with nice view-9

Comfortable stay downtown near sculpture park-7

Comfortable stay downtown near sculpture park-7
Downtown Des Moines
8.6 out of 10, Excellent, (7)
"Great location, clean, everything we needed."
United States
Samantha M.
The price is €159
includes taxes & fees
22 Jan - 23 Jan 2026
Comfortable stay downtown near sculpture park-7

Sleepover: Wonderful 1BD/1BA -Downtown Des Moines

Sleepover: Wonderful 1BD/1BA -Downtown Des Moines
Downtown Des Moines
9.6 out of 10, Exceptional, (8)
"The furniture is very comfortable. The check in and check out is very easy. Also a huge plus is that there a free lot to park in behind the building. Overall a great place to stay . We have stayed there a few times now. "
Canada
Gord J.
The price is €165
includes taxes & fees
23 Dec - 24 Dec
Sleepover: Wonderful 1BD/1BA -Downtown Des Moines

Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (18)
"We loved the nearby Amish grocery store."
United States
Teresa
The price is €143
includes taxes & fees
21 Jan - 22 Jan 2026
Farmhouse Oasis
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

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 €160 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 close to the most popular sights in Winterset, 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?

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!: This holiday home rental outside of Winterset is located next to a golf course, and has a fireplace, a balcony and a BBQ to put you at ease 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.