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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$312 nightly
The price is $349
Oct 20 - Oct 21
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

2. 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, (16 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 multi-story residential building with a stone facade, a small porch, and a garage.

3. 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, (30 reviews)
"Very nice property. Owners were prompt with responses to questions. Would def book again!"
United States
Elizabeth F.
$216 nightly
The price is $242
Oct 5 - Oct 6
Total with taxes and fees
The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
A residential complex with multiple apartment buildings, a swimming pool, and outdoor seating areas.

4. Luxe, First Floor Suite with Garage & Balcony

Luxe, First Floor Suite with Garage & Balcony
West Des Moines
10.0 out of 10, Exceptional, (1 review)
"Great quiet community, close to shopping and restaurants. A nice place to stay with great communication! Will most definitely stay here again in the future. "
United States
Amber T.
$211 nightly
The price is $236
Oct 6 - Oct 7
Total with taxes and fees
Luxe, First Floor Suite with Garage & Balcony
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
Oct 4 - Oct 5
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
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, (2 reviews)
"Great quiet place to stay. Very clean."
United States
Emily R.
$221 nightly
The price is $247
Oct 5 - Oct 6
Total with taxes and fees
Wooded Views | King Bed | No Stairs
A garden with a stream, rocks, and flowers.

7. 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.
$201 nightly
The price is $211
Oct 5 - Oct 6
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
A Staybridge Suites hotel with a brick facade, green roof, and a parking lot with several cars.

8. Suite w/ Fireplace & Full Kitchen | Free Breakfast

Suite w/ Fireplace & Full Kitchen | Free Breakfast
West Des Moines
8.0 out of 10, Very good, (1 review)
"Room was clean. Parking lot was well lit. Nice walking path in the back. Decent breakfast and a happy hour Monday and Tuesday evenings.Workout room could use some updates: one TV was broken and neither TV connected, the elliptical machine didn’t connect/track data."
United States
Nikki F.
$151 nightly
The price is $170
Oct 22 - Oct 23
Total with taxes and fees
Suite w/ Fireplace & Full Kitchen | Free Breakfast
A modern kitchen with stainless steel appliances, dark cabinetry, and a granite countertop.

9. 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, (98 reviews)
"Such a fabulous property and located perfected by lots of fun things to do."
United States
Landon B.
$599 nightly
The price is $671
Oct 4 - Oct 5
Total with taxes and fees
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
A residential house with a well-maintained lawn, a tire sculpture, and a garage.

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

Endless Fun! Family Home w/ Spacious Yard in Clive
3.0 star property
Clive
Endless Fun! Family Home w/ Spacious Yard in Clive
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

11. 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
Oct 5 - Oct 6
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.

12. 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.
$216 nightly
The price is $227
Oct 4 - Oct 5
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A pathway leading to a gated area with lush green foliage on both sides.

13. 3-bedroom townhome in serene West Des Moines with AC

3-bedroom townhome in serene West Des Moines with AC
West Des Moines
8.0 out of 10, Very good, (2 reviews)
"It was a nice place for a quick girls getaway!"
United States
T D.
$251 nightly
The price is $281
Oct 5 - Oct 6
Total with taxes and fees
3-bedroom townhome in serene West Des Moines with AC
A modern house with a stone pillar, a front door with a glass panel, a bench, and a small garden.

14. 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, (21 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.
$661 nightly
The price is $740
Oct 4 - Oct 5
Total with taxes and fees
Convenient functional quiet 5 bedroom 3 bath home in Clive.
An outdoor patio with a fire pit, seating, and a grill area.

15. Sleepover | Classic Studio and Gym - Des Moines

Sleepover | Classic Studio and Gym - Des Moines
Drake
9.0 out of 10, Wonderful, (2 reviews)
"We had a very nice time in Des Moines! The vrbo was very nice and in a super convenient location! Would definitely stay again! "
United States
Bonnie C.
$176 nightly
The price is $199
Nov 1 - Nov 2
Total with taxes and fees
Sleepover | Classic Studio and Gym - Des Moines
A dining room with a wooden table, chairs, a bench, a chandelier, and a potted plant.

16. •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
Oct 25 - Oct 26
Total with taxes and fees
•Delightful 5b stay in Paradise!!•
A house by a lake with a covered porch and a satellite dish.

17. 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
$181 nightly
The price is $190
Oct 5 - Oct 6
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
A single-story house with a front yard, a mailbox, and a tree.

18. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (30 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
Oct 5 - Oct 6
Total with taxes and fees
Farmhouse Oasis
A modern kitchen with a large island, bar stools, and a dining area with striped chairs.

19. Base Camp – Modern Cozy Retreat with Sauna, Hot Tub & Fun for Families in WDM

Base Camp – Modern Cozy Retreat with Sauna, Hot Tub & Fun for Families in WDM
West Des Moines
$1,000 nightly
The price is $1,120
Oct 4 - Oct 5
Total with taxes and fees
Base Camp – Modern Cozy Retreat with Sauna, Hot Tub & Fun for Families in WDM
A residential house with a well-maintained lawn, a tire sculpture, and a garage.

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

Endless Fun! Family Home w/ Spacious Yard in Clive
Clive
9.6 out of 10, Exceptional, (4 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.
Endless Fun! Family Home w/ Spacious Yard in Clive
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

Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

10/10 Excellent
"Clean hotel in safe location. Excellent staff."
steve 2-night trip
Posted less than an hour ago
Days Inn & Suites by Wyndham Des Moines Airport

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 $242 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.