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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$286 nightly
The price is $321
Sep 29 - Sep 30
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A rural landscape with two yurts, a small wooden structure, and a herd of cattle.

2. Grain Bin and outdoor bar with countryside views, cows, & beautiful Iowa scenery

Grain Bin and outdoor bar with countryside views, cows, & beautiful Iowa scenery
Stuart
$262 nightly
The price is $275
Sep 24 - Sep 25
Total with taxes and fees
Grain Bin and outdoor bar with countryside views, cows, & beautiful Iowa scenery
A modern kitchen with a dining area, wooden flooring, and a large window offering a view of the backyard.

3. 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 24 - Sep 25
Total with taxes and fees
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
A swimming pool with lounge chairs, a covered seating area, and a multi-story building with balconies.

4. 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, (29 reviews)
"Great location very nice apartment "
United States
Cindy P.
$220 nightly
The price is $247
Sep 24 - Sep 25
Total with taxes and fees
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
A garden with a stream, rocks, and flowers.

5. 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 24 - Sep 25
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
A modern kitchen with a central island, white cabinets, and a stainless steel refrigerator.

6. Beach Access/Kid Friendly/Park/Office/4BR/2B

Beach Access/Kid Friendly/Park/Office/4BR/2B
Norwalk
9.6 out of 10, Exceptional, (4 reviews)
"Great house, very comfortable, lots of room had everything we could have needed "
United States
Spencer B.
$553 nightly
The price is $619
Sep 27 - Sep 28
Total with taxes and fees
Beach Access/Kid Friendly/Park/Office/4BR/2B
A dining room with a wooden table, chairs, a bench, a chandelier, and a potted plant.

7. •Delightful 5b stay in Paradise!!•

•Delightful 5b stay in Paradise!!•
Waukee
9.8 out of 10, Exceptional, (21 reviews)
"It was perfect for our family getaway!"
United States
justine p.
$386 nightly
The price is $432
Sep 24 - Sep 25
Total with taxes and fees
•Delightful 5b stay in Paradise!!•
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

8. 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.
$181 nightly
The price is $190
Sep 29 - Sep 30
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
A modern kitchen with a built-in microwave, stove, and stainless steel refrigerator.

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

Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines
Cumming
$263 nightly
The price is $276
Sep 27 - Sep 28
Total with taxes and fees
Romantic Couples Cottage: Private Hot Tub + Fireplace + Near Des Moines
A modern living room with a glass coffee table, a sofa, a TV, and a view of the outdoors.

10. 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 24 - Sep 25
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

11. 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, (14 reviews)
"Great place to stay!"
United States
Elizabeth V.
$436 nightly
The price is $488
Oct 5 - Oct 6
Total with taxes and fees
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A house by a lake with a covered porch and a satellite dish.

12. Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and really nice place. The host is professional and kind. I would definitely stay again."
United States
Mike
$172 nightly
The price is $181
Sep 24 - Sep 25
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

13. 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)
"Beautiful place to stay and very accommodating host."
United States
Amy K.
$144 nightly
The price is $161
Sep 30 - Oct 1
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

14. 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.
$191 nightly
The price is $200
Sep 24 - Sep 25
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A modern house with a stone pillar, a front door with a glass panel, a bench, and a small garden.

15. Convenient functional quiet 5 bedroom 3 bath home in Clive.

Convenient functional quiet 5 bedroom 3 bath home in Clive.
Clive
10.0 out of 10, Exceptional, (19 reviews)
"Perfect stay! The home was spacious and clean and was just as great as depicted in the photos! The communications with the host were helpful and check in and check out was smooth,"
United States
Beth N.
$686 nightly
The price is $768
Sep 24 - Sep 25
Total with taxes and fees
Convenient functional quiet 5 bedroom 3 bath home in Clive.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

16. 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, (31 reviews)
"Perfect spot for our family celebrating a graduation. Host was SO Accommodating."
United States
Tim B.
$466 nightly
The price is $522
Sep 27 - Sep 28
Total with taxes and fees
The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown
A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

17. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (11 reviews)
"Nice place"
United States
Dale T.
$203 nightly
The price is $227
Sep 24 - Sep 25
Total with taxes and fees
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A modern kitchen with stainless steel appliances, dark cabinetry, and a granite countertop.

18. LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Waukee
9.6 out of 10, Exceptional, (97 reviews)
"Such a fabulous property and located perfected by lots of fun things to do."
United States
Landon B.
$585 nightly
The price is $655
Oct 4 - Oct 5
Total with taxes and fees
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
A spacious living area with a pool table, a fireplace, and a dining area with a bench and table.

19. RARE Mid-Mod Home. Spacious inside-and-out.

RARE Mid-Mod Home. Spacious inside-and-out.
Urbandale
9.8 out of 10, Exceptional, (16 reviews)
"The family and I had a fantastic time. The house has been nicely remodeled, the beds were comfortable, and the towels are nice quality. The backyard was nice and relaxing and the little lake out back is amazing! If you are looking for a place to stay, I would absolutely recommend this one."
United States
Tino U.
$504 nightly
The price is $565
Sep 27 - Sep 28
Total with taxes and fees
RARE Mid-Mod Home. Spacious inside-and-out.
A staircase with white railings and a potted plant at the bottom.

20. 2-bedroom apartment close to uptown Creston with WiFi and off street parking.

2-bedroom apartment close to uptown Creston with WiFi and off street parking.
Creston
10.0 out of 10, Exceptional, (9 reviews)
"Great little apartment-like spot for stays on Creston. Easy checkin, clean spot, easy checkout."
United States
Samuel
$169 nightly
The price is $189
Sep 28 - Sep 29
Total with taxes and fees
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
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

Country Inn & Suites by Radisson, Des Moines West, IA

Country Inn & Suites by Radisson, Des Moines West, IA

10/10 Excellent
"Very clean nice place"
Joseph 2-night trip
Posted 12 hours ago
Country Inn & Suites by Radisson, Des Moines West, IA

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.