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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winterset vacation rentals

Outdoor dining

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, (14 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.
$311 nightly
The price is $348
Jul 28 - Jul 29
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Property grounds

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, (411 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.
$163 nightly
The price is $171
Jul 28 - Jul 29
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
Exterior

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, (12 reviews)
"Spacious accommodations, clean, and excellent location in a quiet area. Host, Clayton, was very responsive. "
United States
John S.
$159 nightly
The price is $178
Jul 28 - Jul 29
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
Exterior

1st Floor, Stylish & Upgraded Retreat with Garage

1st Floor, Stylish & Upgraded Retreat with Garage
West Des Moines
9.8 out of 10, Exceptional, (19 reviews)
"Will be staying here again no questions asked. I travel lots with work. This place was perfect for a traveling person or couple."
United States
Shane B.
$217 nightly
The price is $243
Jul 28 - Jul 29
Total with taxes and fees
1st Floor, Stylish & Upgraded Retreat with Garage
Exterior

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, (19 reviews)
"A perfect place to relax! This farmhouse was spotless and had everything we needed for a long, comfortable weekend. Lots of seating, comfy beds and bedding, fluffy towels and peaceful surroundings. We loved it here! The last time we were here, we stayed in their barn vrbo, which was also a great place!"
United States
Chris M.
$193 nightly
The price is $202
Jul 28 - Jul 29
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
Smart TV, printers

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, (14 reviews)
"Perfect location, very clean, would definitely stay again! "
United States
Amy P.
$215 nightly
The price is $240
Jul 28 - Jul 29
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Coffee/tea maker, fridge, microwave, oven

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, (17 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
$182 nightly
The price is $191
Aug 9 - Aug 10
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
Smart TV

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 reviews)
"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.
$222 nightly
The price is $233
Jul 28 - Jul 29
Total with taxes and fees
Beautiful 2BR N of Grand near Downtown
Microwave, oven, stovetop

Valley Junction Getaway

Valley Junction Getaway
West Des Moines
10.0 out of 10, Exceptional, (1 review)
"Great place to stay for a night. Everything was clean and neat. "
United States
Nicole C.
$124 nightly
The price is $138
Jul 28 - Jul 29
Total with taxes and fees
Valley Junction Getaway
Outdoor dining

Sleepover | Extraordinary Studio + Gym- Des Moines

Sleepover | Extraordinary Studio + Gym- Des Moines
Drake
10.0 out of 10, Exceptional, (3 reviews)
"Nice place and close to where we needed to be. "
United States
Lori P.
$161 nightly
The price is $182
Jul 28 - Jul 29
Total with taxes and fees
Sleepover | Extraordinary Studio + Gym- Des Moines
Exterior

Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (37 reviews)
"What a great place to stay! "
United States
Annie P.
$245 nightly
The price is $274
Jul 28 - Jul 29
Total with taxes and fees
Beautiful home minutes from downtown!
Coffee/tea maker, fridge, microwave, oven

Sleepover | Dashing 1BD/1BA - Des Moines

Sleepover | Dashing 1BD/1BA - Des Moines
West Des Moines
9.0 out of 10, Wonderful, (2 reviews)
"Good location near shops and highway."
United States
Liliam W.
$188 nightly
The price is $213
Jul 28 - Jul 29
Total with taxes and fees
Sleepover | Dashing 1BD/1BA - Des Moines
Terrace/patio

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

Sleepover | Charming 1BD/1BA - Downtown Des Moines
Woodland Heights
10.0 out of 10, Exceptional, (2 reviews)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
$188 nightly
The price is $213
Jul 28 - Jul 29
Total with taxes and fees
Sleepover | Charming 1BD/1BA - Downtown Des Moines
Bar (on property)

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, (12 reviews)
"Great place to stay!"
United States
Elizabeth V.
$450 nightly
The price is $504
Jul 28 - Jul 29
Total with taxes and fees
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
Exterior

Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly

Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly
Drake
10.0 out of 10, Exceptional, (1 review)
"It was well organized and clean. The on site parking was super convenient. Host was very response, which I really appreciated. Would stay here again!"
United States
Elvis G.
$183 nightly
The price is $205
Jul 28 - Jul 29
Total with taxes and fees
Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly
Exterior

West Des Moines Bungalow

West Des Moines Bungalow
West Des Moines
9.4 out of 10, Exceptional, (16 reviews)
"Stayed there for a softball tournament. Good location, house was clean. "
United States
megan h.
$170 nightly
The price is $190
Jul 28 - Jul 29
Total with taxes and fees
West Des Moines Bungalow
WiFi (free), bed sheets

Quiet Pet-Friendly Studio Near Hospitals

Quiet Pet-Friendly Studio Near Hospitals
Downtown Des Moines
8.8 out of 10, Excellent, (11 reviews)
"Pretty nice spot"
United States
Alberto P.
$183 nightly
The price is $190
Jul 28 - Jul 29
Total with taxes and fees
Quiet Pet-Friendly Studio Near Hospitals
Exterior

Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.6 out of 10, Exceptional, (4 reviews)
"It was more than we expected, a perfect place to get away for some peace and quiet. Super clean and very well equipped with everything we needed. Can't wait to stay again!"
United States
Eric F.
$160 nightly
The price is $168
Aug 16 - Aug 17
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
Exterior

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, (27 reviews)
"Well equipped, clean unit on 3rd floor, easy checkin and very responsive host. Great stay."
United States
jennifer d.
$301 nightly
The price is $337
Aug 25 - Aug 26
Total with taxes and fees
The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
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

Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston

8/10 Good
"Staff was absolutely amazing! Unfortunately the hot tub was down but still a very nice hotel with very helpful and knowledgeable staff, they helped us find great restaurants and plenty to do!"
Trin 2-night trip
Posted less than an hour ago
Stoney Creek Hotel Des Moines - Johnston

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 $178 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?

Heated Pool Hot Tub PicklebalMovieTheaterPoolTable GameR Golf: Visitors like this Winterset vacation home rental. It offers an outdoor pool, a fireplace, 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. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Winterset?

With 6 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, Cedar Bridge and Roseman 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.