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 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winterset vacation rentals

Outdoor dining

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 was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!"
United States
Heather G.
$318 nightly
The price is $357
Aug 17 - Aug 18
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Property grounds

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, (413 reviews)
"The barn and grounds are immaculate. This place is enchanting. Stay here. You will not be disappointed. "
United States
Barbara O.
$164 nightly
The price is $172
Aug 16 - Aug 17
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.
Exterior

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
9.4 out of 10, Exceptional, (13 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 17 - Aug 18
Total with taxes and fees
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
Exterior

4. 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
Aug 18 - Aug 19
Total with taxes and fees
Spacious Farmhouse beautifully decorated waiting for laughs and memories
Smart TV, printers

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.
$221 nightly
The price is $247
Aug 17 - Aug 18
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Exterior

6. 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 18 - Aug 19
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
Bar (on property)

7. 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...
WiFi (free), bed sheets

8. Stylish and cozy studio near Western Gateway Park, combining comfort, convenience, and a prime Downtown location.

Stylish and cozy studio near Western Gateway Park, combining comfort, convenience, and a prime Downtown location.
Downtown Des Moines
10.0 out of 10, Exceptional, (5 reviews)
"Everything was clean"
United States
Shelby L.
$189 nightly
The price is $197
Aug 30 - Aug 31
Total with taxes and fees
Stylish and cozy studio near Western Gateway Park, combining comfort, convenience, and a prime Downtown location.
Coffee/tea maker, fridge, microwave, oven

9. 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.
$191 nightly
The price is $216
Aug 23 - Aug 24
Total with taxes and fees
Sleepover | Dashing 1BD/1BA - Des Moines
Property grounds

10. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (28 reviews)
"This was a beautiful rural setting. We enjoyed our stay very much. "
United States
Norman Z.
$190 nightly
The price is $200
Sep 14 - Sep 15
Total with taxes and fees
Farmhouse Oasis
Smart TV

11. 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
9.0 out of 10, Wonderful, (10 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.
$159 nightly
The price is $178
Aug 24 - Aug 25
Total with taxes and fees
Cozy #2 for YOU! 1-bed apartment in fantastic Sherman Hill Downtown Des Moines
Exterior

12. 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.
$247 nightly
The price is $277
Aug 27 - Aug 28
Total with taxes and fees
Beautiful home minutes from downtown!
Exterior

13. 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.
$319 nightly
The price is $358
Aug 17 - Aug 18
Total with taxes and fees
1st Floor, Stylish & Upgraded Retreat with Garage
Exterior

14. Sleepover | Marvelous 1BD/1BA - Des Moines

Sleepover | Marvelous 1BD/1BA - Des Moines
West Des Moines
10.0 out of 10, Exceptional, (4 reviews)
"We stayed at the Flux apartments in downtown. Our accommodation was exceptional in all respects. Thank you for your hospitality!"
United States
Miriam G.
$191 nightly
The price is $216
Aug 23 - Aug 24
Total with taxes and fees
Sleepover | Marvelous 1BD/1BA - Des Moines
Outdoor dining

15. Sleepover | Attractive Studio and Gym - Des Moines

Sleepover | Attractive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (3 reviews)
"Very convenient place to stay for the Drake Relays. Would definitely look to stay there again."
United States
Josh
$191 nightly
The price is $233
Aug 31 - Sep 1
Total with taxes and fees
Sleepover | Attractive Studio and Gym - Des Moines
Smart TV

16. • 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
Aug 23 - Aug 24
Total with taxes and fees
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Interior

17. Fun & Charming 1BR Apt near Drake

Fun & Charming 1BR Apt near Drake
Drake
8.0 out of 10, Very Good, (2 reviews)
"Abner is amazing. Communication was as smooth as can be, the place was left in great condition, and the house rules were respected. I hope to host them again in the future!"
United States
AbnerG
$231 nightly
The price is $240
Aug 30 - Aug 31
Total with taxes and fees
Fun & Charming 1BR Apt near Drake
TV

18. Cozy Bungalow Retreat

Cozy Bungalow Retreat
Greater South Side
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. Quiet and cozy"
United States
Christopher G.
$192 nightly
The price is $214
Aug 23 - Aug 24
Total with taxes and fees
Cozy Bungalow Retreat
Exterior

19. 2 Story House 2 blocks from Ingersoll<br>*Fenced in Patio <br>* Formal dining room<br>*Hardwood flooring<br>*Newly remodeled Kitchen <br>*Google Fiber Internet

2 Story House 2 blocks from Ingersoll<br>*Fenced in Patio <br>* Formal dining room<br>*Hardwood flooring<br>*Newly remodeled Kitchen <br>*Google Fiber Internet
Woodland Heights
4.0 out of 10, (2 reviews)
"We were told the house was “cleaned” the day before we arrived. NOT TRUE. There was a dead misuse in the basement along with a bunch of filthy towels. The backdoor didn’t lock. The TV didn’t work. There was a used paper towel roll for use to use. We had the house for two days but left after the first night, the following morning as I was packing I saw a mouse run under the stove. Never again"
United States
benjamin s.
$218 nightly
The price is $228
Aug 30 - Aug 31
Total with taxes and fees
2 Story House 2 blocks from Ingersoll<br>*Fenced in Patio <br>* Formal dining room<br>*Hardwood flooring<br>*Newly remodeled Kitchen <br>*Google Fiber Internet
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

10/10 Excellent
"This was my second stay at this property, and I chose to return there rather than staying at a less expensive place. Coffee and cold drinking water are available in the lobby 24/7. The breakfast has a good .variety, the room is very comfortable and nicely decorated. The Wi-Fi is excellent. There is a nice exercise room. There are several restaurants within walking distance."
Christina 1-night trip
Posted 11 hours 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?

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10: Visitors like this Winterset vacation home rental. It is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 garden, a selection of games, and a hot tub 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, 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.