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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winterset vacation 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

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Winterset
10.0 out of 10, Exceptional, (15 reviews)
"The house in Winterset was perfect in every way. It was beautifully furnished and extremely comfortable. We are so glad we stayed there."
United States
Nickay M.
$775 nightly
The price is $868
Oct 6 - Oct 7
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A garden with a stream, rocks, and flowers.

2. 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, (414 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
Sep 9 - Sep 10
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
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

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
West Des Moines
9.2 out of 10, Wonderful, (15 reviews)
$144 nightly
The price is $161
Sep 9 - Sep 10
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

4. 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, (13 reviews)
"Great place to stay!"
United States
Elizabeth V.
$436 nightly
The price is $488
Sep 10 - Sep 11
Total with taxes and fees
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
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

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Waukee
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location, very clean, would definitely stay again! "
United States
Amy P.
$220 nightly
The price is $246
Sep 13 - Sep 14
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
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

Spacious Farmhouse beautifully decorated waiting for laughs and memories
New Virginia
10.0 out of 10, Exceptional, (21 reviews)
"Very nice place to stay."
United States
Todd W.
$190 nightly
The price is $199
Sep 9 - Sep 10
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

7. 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, (18 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
$180 nightly
The price is $189
Sep 11 - Sep 12
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (37 reviews)
"Very nice quiet place to stay. Beds were nice and comfy. Nice kitchen and laundry area.We enjoyed our stay"
United States
Doreen
$332 nightly
The price is $372
Sep 9 - Sep 10
Total with taxes and fees
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
An outdoor patio with a fire pit, seating, and a grill area.

9. Sleepover | Impressive Studio and Gym - Des Moines

Sleepover | Impressive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (3 reviews)
"Easy access to drake university was great"
United States
Gerardo
$165 nightly
The price is $187
Sep 9 - Sep 10
Total with taxes and fees
Sleepover | Impressive Studio and Gym - Des Moines
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 •

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Indianola
9.4 out of 10, Exceptional, (23 reviews)
"Had a great stay, will come back!"
United States
Spring A.
$229 nightly
The price is $256
Sep 9 - Sep 10
Total with taxes and fees
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
An outdoor patio with a fire pit, seating, and a grill area.

11. Sleepover | Extraordinary Studio + Gym- Des Moines

Sleepover | Extraordinary Studio + Gym- Des Moines
Drake
10.0 out of 10, Exceptional, (4 reviews)
"Nice place and close to where we needed to be. "
United States
Lori P.
$165 nightly
The price is $187
Sep 9 - Sep 10
Total with taxes and fees
Sleepover | Extraordinary Studio + Gym- Des Moines
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

Cozy #2 for YOU! 1-bed apartment in fantastic Sherman Hill Downtown Des Moines
Downtown Des Moines
9.2 out of 10, Wonderful, (12 reviews)
"The location is incredible, close to everything going on downtown or at Drake, and includes off-street parking! Check in is seamless and hosts are responsive! Perfect landing spot for a weekend in Des Moines with a great location and solid amenities!"
United States
Nathan S.
$156 nightly
The price is $175
Sep 9 - Sep 10
Total with taxes and fees
Cozy #2 for YOU! 1-bed apartment in fantastic Sherman Hill Downtown Des Moines
A single-story house with a front yard, a mailbox, and a tree.

13. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (28 reviews)
"The property was great and would stay again and recommend to family and friends if ciming into town."
United States
Michael D.
$165 nightly
The price is $173
Sep 21 - Sep 22
Total with taxes and fees
Farmhouse Oasis
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!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (41 reviews)
"Very clean and spacious. Good location to downtown. Very comfortable home. Would recommend and would stay again!!"
United States
Melissa W.
$237 nightly
The price is $265
Sep 9 - Sep 10
Total with taxes and fees
Beautiful home minutes from downtown!
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

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.6 out of 10, Exceptional, (5 reviews)
"Very clean and really nice place. The host is professional and kind. I would definitely stay again."
United States
Mike
$171 nightly
The price is $180
Sep 11 - Sep 12
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
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

The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
West Des Moines
9.8 out of 10, Exceptional, (28 reviews)
"Great location very nice apartment "
United States
Cindy P.
$222 nightly
The price is $248
Oct 6 - Oct 7
Total with taxes and fees
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

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

Sleepover | Lovely 1BD/BA + High Ceilings - DSM
West Des Moines
$170 nightly
The price is $193
Sep 9 - Sep 10
Total with taxes and fees
Sleepover | Lovely 1BD/BA + High Ceilings - DSM
A modern kitchen with a built-in microwave, stove, and stainless steel refrigerator.

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

Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines
Cumming
$292 nightly
The price is $307
Sep 28 - Sep 29
Total with taxes and fees
Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines
A multi-story building with a flat roof, large windows, and a sign reading 'KEYSTONE'.

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

Sleepover | Alluring 1BD/1BA - Des Moines
West Des Moines
$176 nightly
The price is $199
Sep 9 - Sep 10
Total with taxes and fees
Sleepover | Alluring 1BD/1BA - Des Moines
A living room with a ceiling fan, a TV, a sofa, and a coffee table.

20. Sherman Hills Historic Retreat #6

Sherman Hills Historic Retreat #6
Downtown Des Moines
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Rodney P.
$155 nightly
The price is $174
Sep 30 - Oct 1
Total with taxes and fees
Sherman Hills Historic Retreat #6
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

Wildwood Lodge

Wildwood Lodge

8/10 Good
"The property was super clean and the staff was amazing as usual. The pool was nice, but the Hot Tub was down. That's the only bad thing about the place. Breakfast was very tasty."
Jeffrey 2-night trip
Posted less than an hour ago
Wildwood Lodge

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 $161 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?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: Visitors like this Winterset vacation home rental. It offers a fireplace, a patio, 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. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winterset?

With 5 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, Clark Tower and Cedar 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.