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Winterset Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in Winterset

Our top choices for Winterset holiday rentals

Comfortable and Spacious 3 Bedroom Home
Interior

Comfortable and Spacious 3 Bedroom Home

9.8 out of 10, Exceptional, (56)
"We enjoyed our stay immensely! "
Comfortable and Spacious 3 Bedroom Home
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (62)
"Good space and size for larger groups."
The price is HK$2,103
HK$5,104 total
includes taxes & fees
25 Aug - 26 Aug
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Beautiful home minutes from downtown!
Games room

Beautiful home minutes from downtown!

9.2 out of 10, Wonderful, (15)
"My family and I had a nice stay. The house was spot on to the description, and you can tell the host goes above and beyond to make guests feel comfortable. "
The price is HK$914
HK$2,171 total
includes taxes & fees
25 Aug - 26 Aug
Beautiful home minutes from downtown!
Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!
Outdoor spa tub

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 HK$1,555
HK$3,046 total
includes taxes & fees
26 Aug - 27 Aug
Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines
Dining

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

9.6 out of 10, Exceptional, (175)
"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
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
Property grounds

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 HK$872
HK$2,316 total
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
Interior

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 HK$3,322
HK$6,504 total
includes taxes & fees
25 Aug - 26 Aug
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
The Royal Palace/pool/Jacuzzi/Theater/Pool table/ Fire pit.
Fridge, microwave, oven, stovetop

The Royal Palace/pool/Jacuzzi/Theater/Pool table/ Fire pit.

10.0 out of 10, Exceptional, (1)
"Our family from different parts of Iowa met for a mini vacation. Great location, great house, great amenities!"
The Royal Palace/pool/Jacuzzi/Theater/Pool table/ Fire pit.
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood
Microwave, oven, stovetop, dishwasher

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
Vibrant Downtown Condo with Skywalk Access #5
Property grounds

Vibrant Downtown Condo with Skywalk Access #5

8.2 out of 10, Very good, (10)
"Love staying here"
The price is HK$453
HK$1,254 total
includes taxes & fees
26 Aug - 27 Aug
Vibrant Downtown Condo with Skywalk Access #5
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
Exterior

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

9.6 out of 10, Exceptional, (29)
"Very quiet location just out of town. Lots of space inside and out. Great hosts. "
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown
Interior

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 HK$1,250
HK$3,352 total
includes taxes & fees
25 Aug - 26 Aug
The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown
Lovely 2-bedroom apartment in Sherman Hill-4
Fridge, microwave, oven, stovetop

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 HK$757
HK$1,391 total
includes taxes & fees
25 Aug - 26 Aug
Lovely 2-bedroom apartment in Sherman Hill-4
Vibrant Downtown Condo with Skywalk Access #3
Property grounds

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...
The price is HK$453
HK$1,254 total
includes taxes & fees
26 Aug - 27 Aug
Vibrant Downtown Condo with Skywalk Access #3
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
Interior

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 HK$2,806
HK$6,968 total
includes taxes & fees
25 Aug - 26 Aug
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
Walkable Downtown Townhome
Property grounds

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!"
The price is HK$1,555
HK$3,589 total
includes taxes & fees
26 Aug - 27 Aug
Walkable Downtown Townhome
Quiet Studio on Grand - Heart of Downtown!
Free WiFi, bed sheets

Quiet Studio on Grand - Heart of Downtown!

10.0 out of 10, Exceptional, (3)
"Thumbs up"
The price is HK$378
HK$7,466 total
includes taxes & fees
25 Aug - 26 Aug
Quiet Studio on Grand - Heart of Downtown!
House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood
Outdoor dining

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
Quiet Studio on Grand Near Hospitals!
Fridge, microwave, oven, stovetop

Quiet Studio on Grand Near Hospitals!

8.6 out of 10, Excellent, (9)
"Older building, but the apartment was clean and nice. "
Quiet Studio on Grand Near Hospitals!
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!
Fridge, microwave, oven, stovetop

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 HK$1,611
HK$4,054 total
includes taxes & fees
25 Aug - 26 Aug
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!
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
"Great place to stay "
Theresa 2-night trip
Posted 9 hours ago
Days Inn & Suites by Wyndham Des Moines Airport

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?

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!: This holiday home rental outside of Winterset is located next to a golf course, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.