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Winterset Holiday Rentals

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Holiday Rentals in Winterset

Our top choices for Winterset holiday rentals

Comfortable and Spacious 3 Bedroom Home

9.8 out of 10, Exceptional, (57)
"We enjoyed our stay immensely! "
Comfortable and Spacious 3 Bedroom Home

Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

2.0 star property
8.8 out of 10, Excellent, (26)
"Wonderful property and host! "
The price is AU$438
includes taxes & fees
8 Sept - 9 Sept
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines

9.6 out of 10, Exceptional, (176)
"Beautiful home! Great owners! Ample parking. A few blocks away from the Valley Junction business district. Will stay again. "
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

9.2 out of 10, Wonderful, (55)
"Excellent location and clean property. Plenty of things to do in the area as well as comfortable living space at the property."
The price is AU$1,115
includes taxes & fees
9 Sept - 10 Sept
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

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

9.8 out of 10, Exceptional, (62)
"This was great for our extended family to stay. Plenty of room for everyone. "
The price is AU$1,014
includes taxes & fees
4 Sept - 5 Sept
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

Beautiful home minutes from downtown!

9.4 out of 10, Exceptional, (16)
"Overall we had a nice time and would come back. It was convenient for visiting family without being in each other’s way."
The price is AU$428
includes taxes & fees
5 Sept - 6 Sept
Beautiful home minutes from downtown!

Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!

9.6 out of 10, Exceptional, (23)
"Clean & thoughtful touches! I loved the outdoor patio. The bedroom size is in keeping with the house, comfortable & was well represented from the pictures. The washing machine & dryer were nice to have - especially after using the hot tub."
The price is AU$625
includes taxes & fees
2 Sept - 3 Sept
Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!

Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood

9.6 out of 10, Exceptional, (5)
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood

The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house for our family to stay and gather between weddings events! Easy to get to and had lots of space to hang out. "
The price is AU$664
includes taxes & fees
1 Sept - 2 Sept
The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown

Walkable Downtown Townhome

10.0 out of 10, Exceptional, (2)
"We met up for an adult weekend getaway. The house is easy walking distance to food and drinks. Nice and clean with lots of space for everyone!"
Walkable Downtown Townhome

Beautiful remodeled historic Drake Univ home minutes from downtown and all metro

9.8 out of 10, Exceptional, (49)
"Everything was great. Anything we needed was there only thing we had a problem was there were ants in the kitchen and bathrooms, But other than that the stay was comfortable and great. "
The price is AU$1,289
includes taxes & fees
31 Aug - 1 Sept
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro

Vibrant Downtown Condo with Skywalk Access #3

6.0 out of 10, (3)
"There were a number of things I didn't like. First, there was no one available to assist or answer questions for the first 2 days there. Secondly, there was unexpected a lot of noise outside the unit a 5am. Third, they said no pets allowed, but we experienced animal fur in the unit. We have a crawling infant and there was a lot of fur on the bottom of his high chair discovered as we were loading our van to leave. The unit and building was very secure, but there was no information given...
Vibrant Downtown Condo with Skywalk Access #3

AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

9.8 out of 10, Exceptional, (64)
"Our stay was an amazing experience and the host was very helpful with any and all questions we had. I would recommend this host/property to any of my family or friends!"
The price is AU$1,474
includes taxes & fees
29 Sept - 30 Sept
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood

9.8 out of 10, Exceptional, (12)
"We were in town for a basketball tournament. The house was very comfortable and clean. Location is excellent-amazing little cafe right next door was a bonus. Communication, check in, and overall comfort was excellent. "
House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

9.4 out of 10, Exceptional, (66)
"Very nice place, great size for our work team in town for training. "
The price is AU$803
includes taxes & fees
1 Sept - 2 Sept
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

Vibrant Downtown Condo with Skywalk Access #5

7.8 out of 10, Good, (11)
"Love staying here"
Vibrant Downtown Condo with Skywalk Access #5

Lovely 2-bedroom apartment in Sherman Hill-4

8.4 out of 10, Very good, (17)
"Clean and worked well for our stay in Des Moines"
The price is AU$292
includes taxes & fees
31 Aug - 1 Sept
Lovely 2-bedroom apartment in Sherman Hill-4

Spacious 5-bedroom house close to everything in Waukee, IA

10.0 out of 10, Exceptional, (7)
The price is AU$987
includes taxes & fees
2 Sept - 3 Sept
Spacious 5-bedroom house close to everything in Waukee, IA

Downtown Skyline Views in Modern Townhome with Rooftop Patios

10.0 out of 10, Exceptional, (33)
"We had a great time and an easy stay walking distance from several great spots."
The price is AU$506
includes taxes & fees
1 Sept - 2 Sept
Downtown Skyline Views in Modern Townhome with Rooftop Patios

Quiet Studio on Grand - Heart of Downtown!

10.0 out of 10, Exceptional, (4)
"Everything was clean"
The price is AU$1,481
includes taxes & fees
31 Aug - 1 Sept
Quiet Studio on Grand - Heart of Downtown!
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

Find out more about Winterset

Find out more about Winterset

Everything you need to know about Winterset holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winterset holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterset holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterset holiday rentals we have selected for you start as low as AU$292 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Winterset?

Yes, there are holiday rentals close to the most popular sights in Winterset, or you can select a more secluded option if you're looking for 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 holiday rentals that Winterset has to offer?

Comfortable and Spacious 3 Bedroom Home: This holiday home rental outside of Winterset is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winterset?

With 4 Expedia holiday rentals, you're guaranteed 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, Madison County Courthouse and Cedar Bridge are other places worth a visit.

What are holiday rentals like in Winterset?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterset. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.