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 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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.
$314 nightly
The price is $351
Sep 1 - Sep 2
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

2. 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)
"Spacious accommodations, clean, and excellent location in a quiet area. Host, Clayton, was very responsive. "
United States
John S.
$144 nightly
The price is $161
Aug 30 - Aug 31
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A garden with a stream, rocks, and flowers.

3. 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, (413 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.
$164 nightly
The price is $172
Aug 30 - Aug 31
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
A modern building with a reflective pool in front.

4. Top Floor, Modern & Upgraded with Pool Views

Top Floor, Modern & Upgraded with Pool Views
West Des Moines
8.0 out of 10, Very Good, (4 reviews)
"We were here to help our daughter move. The apartment is in the same complex which was very helpful. There is plenty to do if here for vacation. The two state parks we went to were fairly close and nice. There are many stores, a mall, and plenty of restaurants within a ten minute drive. Des Moines is 20-30 minutes."
United States
H and P H.
$232 nightly
The price is $260
Aug 30 - Aug 31
Total with taxes and fees
Top Floor, Modern & Upgraded with Pool Views
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

5. 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 2 - Sep 3
Total with taxes and fees
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A house with a swimming pool, a covered patio, and a stone chimney.

6. Wooded Views | King Bed | No Stairs

Wooded Views | King Bed | No Stairs
West Des Moines
10.0 out of 10, Exceptional, (1 review)
"Great quiet place to stay. Very clean."
United States
Emily R.
Wooded Views | King Bed | No Stairs
A swimming pool with lounge chairs, a covered seating area, and a multi-story building with balconies.

7. 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.
$245 nightly
The price is $274
Sep 1 - Sep 2
Total with taxes and fees
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

8. 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.
$223 nightly
The price is $249
Sep 5 - Sep 6
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
A modern kitchen with a dining area, wooden flooring, and a large window offering a view of the backyard.

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (36 reviews)
"Very nice quiet place to stay. Beds were nice and comfy. Nice kitchen and laundry area.We enjoyed our stay"
United States
Doreen
$328 nightly
The price is $367
Sep 1 - Sep 2
Total with taxes and fees
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

10. 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.
$183 nightly
The price is $192
Aug 31 - Sep 1
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

11. 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.
$193 nightly
The price is $202
Aug 30 - Aug 31
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A residential house with a well-maintained lawn, a tire sculpture, and a garage.

12. Endless Fun! Family Home w/ Spacious Yard in Clive

Endless Fun! Family Home w/ Spacious Yard in Clive
3.0 star property
Clive
$432 nightly
The price is $484
Aug 31 - Sep 1
Total with taxes and fees
Endless Fun! Family Home w/ Spacious Yard in Clive
A living room with a sofa, ottoman, lamp, TV, and a painting on the wall.

13. Cozy Bungalow Retreat

Cozy Bungalow Retreat
Greater South Side
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay. Quiet and cozy"
United States
Christopher G.
$176 nightly
The price is $197
Aug 30 - Aug 31
Total with taxes and fees
Cozy Bungalow Retreat
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, (39 reviews)
"The house is bigger on the inside than it looks from/on the outside our party of 5 we had plenty of room & if in Des Moines again i would definitely stay here again "
United States
CARLOS W.
$248 nightly
The price is $278
Aug 30 - Aug 31
Total with taxes and fees
Beautiful home minutes from downtown!
A residential house with a well-maintained lawn, a tire sculpture, and a garage.

15. Endless Fun! Family Home w/ Spacious Yard in Clive

Endless Fun! Family Home w/ Spacious Yard in Clive
Clive
9.4 out of 10, Exceptional, (3 reviews)
"There were 6 of us here to bicycle the Raccoon River valley trail and the property was very close to the trail. We all slept well, loved sitting in the back yard and gathering inside. It was the perfect haven each evening. We had plenty of room and really loved the house."
United States
delores C.
$442 nightly
The price is $495
Aug 31 - Sep 1
Total with taxes and fees
Endless Fun! Family Home w/ Spacious Yard in Clive
A house by a lake with a covered porch and a satellite dish.

16. 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
$160 nightly
The price is $168
Sep 11 - Sep 12
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
A spacious living area with a red sofa, wooden flooring, a flat-screen TV, and a large window with blinds.

17. • 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.
$232 nightly
The price is $259
Sep 2 - Sep 3
Total with taxes and fees
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
A multi-story building with a flat roof, large windows, and a sign reading 'KEYSTONE'.

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

Sleepover | Alluring 1BD/1BA - Des Moines
West Des Moines
$178 nightly
The price is $202
Aug 30 - Aug 31
Total with taxes and fees
Sleepover | Alluring 1BD/1BA - Des Moines

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

Sleepover | Lovely 1BD/BA + High Ceilings - DSM
West Des Moines
$178 nightly
The price is $202
Aug 30 - Aug 31
Total with taxes and fees
Sleepover | Lovely 1BD/BA + High Ceilings - DSM
A modern hotel lobby with a central island, seating area, and a kitchenette.

20. Free Breakfast, Indoor Pool, Hot Tub | King Studio

Free Breakfast, Indoor Pool, Hot Tub | King Studio
West Des Moines
$115 nightly
The price is $129
Sep 6 - Sep 7
Total with taxes and fees
Free Breakfast, Indoor Pool, Hot Tub | King Studio
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

Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

10/10 Excellent
"Love the history of the building Parking is challenging but worth figuring out compared to 40.00 valet"
Michael 1-night trip
Posted 2 hours ago
Hotel Fort Des Moines, Curio Collection by Hilton

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 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.