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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 reviews)
"The house was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!"
United States
Heather G.
The price is £251
includes taxes & fees
31 Mar - 1 Apr
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

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, (12 reviews)
"Lori and Les make you feel right at home. They go above and beyond to ensure you have everything you could need and more. The farm is so peaceful and watching the animals is entertaining."
United States
Valerie
The price is £145
includes taxes & fees
8 Apr - 9 Apr
The Hen House Country Living with Farm Life Appeal Indianola, IA

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, (408 reviews)
"Amazing property "
United States
Anonymous traveller
The price is £140
includes taxes & fees
5 Apr - 6 Apr
Beautiful Rustic Barn just waiting for you to kick back and relax.

Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.0 out of 10, Wonderful, (2 reviews)
"This was our first stay at a place like this. It was an incredibly relaxing stay. Host was very responsive even before our stay with any questions. I plan to come back! "
United States
Kristy A.
The price is £129
includes taxes & fees
29 Mar - 30 Mar
Cozy pond house nestled in nature waiting for you to enjoy

Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (30 reviews)
"What a great place to stay! "
United States
Annie P.
The price is £204
includes taxes & fees
30 Mar - 31 Mar
Beautiful home minutes from downtown!

• 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 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is £180
includes taxes & fees
30 Mar - 31 Mar
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

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

Sleepover | Charming 1BD/1BA - Downtown Des Moines
Woodland Heights
10.0 out of 10, Exceptional, (1 review)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
The price is £167
includes taxes & fees
29 Mar - 30 Mar
Sleepover | Charming 1BD/1BA - Downtown Des Moines

Sherman Hill Hide-a-way

Sherman Hill Hide-a-way
Downtown Des Moines
10.0 out of 10, Exceptional, (3 reviews)
"Good stay."
United States
Nick & Heather W.
The price is £124
includes taxes & fees
12 Apr - 13 Apr
Sherman Hill Hide-a-way

Historic Valley Junction Loft

Historic Valley Junction Loft
West Des Moines
9.4 out of 10, Exceptional, (26 reviews)
"Spacious, apartment in a beautiful century-old brick building with an overlook of historic 5th St. Clean and well-maintained, and great location for a fun stay."
United States
Gene
The price is £98
includes taxes & fees
7 Apr - 8 Apr
Historic Valley Junction Loft

Sleepover | Attractive Studio and Gym - Des Moines

Sleepover | Attractive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (2 reviews)
"Clean and quiet for our stay. "
United States
Jackie
The price is £160
includes taxes & fees
12 Apr - 13 Apr
Sleepover | Attractive Studio and Gym - Des Moines

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (27 reviews)
"Enjoyed our stay. Especially appreciated the snow removal! Will stay here again! "
United States
Meredith B.
The price is £303
includes taxes & fees
30 Mar - 31 Mar
Spacious 4BR Home • WiFi • Family-Friendly • Waukee

Fun & Charming 1BR Apt near Drake

Fun & Charming 1BR Apt near Drake
Drake
8.0 out of 10, Very good, (2 reviews)
"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
The price is £197
includes taxes & fees
12 Apr - 13 Apr
Fun & Charming 1BR Apt near Drake

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Woodland Heights
9.4 out of 10, Exceptional, (73 reviews)
"Awesome place for a large group! My dance team stayed here and loved it. Would definitely recommend! Lots of great amenities and plenty of room to hang out. They even had it decorated for Christmas which we loved!"
United States
Halle R.
The price is £359
includes taxes & fees
30 Mar - 31 Mar
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

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
8.4 out of 10, Very good, (5 reviews)
"The location was absolutely perfect being on the very edge of Des Moines. It was quiet, no city distractions and very private. The space was very clean and Clayton was very friendly and personable. We definitely would stay again!"
United States
Melissa C.
The price is £136
includes taxes & fees
29 Mar - 30 Mar
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown
Windsor Heights
10.0 out of 10, Exceptional, (20 reviews)
"The Love Shack was a wonderful place for our family to gather for the weekend and wedding plan! The home was spotless, all the beds were comfy and it had everything you needed for a nice stay. Highly recommend! "
United States
Missy
The price is £357
includes taxes & fees
29 Mar - 30 Mar
The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Urbandale
9.4 out of 10, Exceptional, (77 reviews)
"Excellent communication lots of amenities. We were very happy with our stay."
United States
Shannon W.
The price is £316
includes taxes & fees
30 Mar - 31 Mar
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Woodland Heights
10.0 out of 10, Exceptional, (4 reviews)
"Responsive host and great little place to stay. This was our second stay here and would stay again."
United States
Jeff C.
The price is £171
includes taxes & fees
30 Mar - 31 Mar
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Comfortable 3-bedroom, 1.5-bathroom duplex apartment with full kitchen, laundry, and off-street parking. Minutes from Drake University and downtown Des Moines.

Comfortable 3-bedroom, 1.5-bathroom duplex apartment with full kitchen, laundry, and off-street parking. Minutes from Drake University and downtown Des Moines.
Waterbury
7.6 out of 10, Good, (8 reviews)
"Great place! Worked very well for the 4 of us. Thanks very much. We will stay here again in the future!"
United States
Tom H.
The price is £225
includes taxes & fees
29 Mar - 30 Mar
Comfortable 3-bedroom, 1.5-bathroom duplex apartment with full kitchen, laundry, and off-street parking. Minutes from Drake University and downtown Des Moines.

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, (23 reviews)
"Great location very nice apartment "
United States
Cindy P.
The price is £178
includes taxes & fees
30 Mar - 31 Mar
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

Sleepover | Alluring 1BD/1BA - Des Moines

Sleepover | Alluring 1BD/1BA - Des Moines
West Des Moines
The price is £141
includes taxes & fees
29 Mar - 30 Mar
Sleepover | Alluring 1BD/1BA - 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

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 £98 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?

Modern home on acreage with pond, trails, rolling hills, and sunset views: This highly rated holiday home rental in Winterset is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Winterset?

With 6 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, Roseman Bridge and Clark Tower 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.