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Winterset Holiday Rentals

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Holiday Rentals in Winterset

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

2.0 star property
9.6 out of 10, Exceptional, (11)
"This property has plenty of space. The living room, dinning room and kitchen can accommodate a larger group. Comfortable beds in all the bedrooms. We would book this property again."
The price is AU$445
includes taxes & fees
10 Mar - 11 Mar
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Executive Living 2min to Jordan Creek 6 bed/5 bath near Jordan Creek Mall!

10.0 out of 10, Exceptional, (33)
"Family Christmas for a large group, worked out perfectly. Great communication with owner."
Executive Living 2min to Jordan Creek 6 bed/5 bath near Jordan Creek Mall!

Downtown Skyline Views in Modern Townhome with Rooftop Patios

9.8 out of 10, Exceptional, (17)
"Clean and comfortable. A wonderfully responsive host."
The price is AU$376
includes taxes & fees
23 Feb - 24 Feb
Downtown Skyline Views in Modern Townhome with Rooftop Patios

SPACIOUS LUXURY- PARTY BARN… PL TBl, PNG PNG, ARCADE, PATIOS. ACCESS TO POOLS!

10.0 out of 10, Exceptional, (58)
"It was the perfect place for our family to be together to celebrate and play games in a homey place rather than hotel rooms. The property would have received 5 stars, but the master shower water never got hot, only warmish even after running it for a long time. I was also disappointed that the master bed has two twin mattresses joined, leaving an uncomfortable crack between your partner. I would recommend a foam T wedge being added or a regular king mattress to fix this problem. Otherwise, we...
The price is AU$1,505
includes taxes & fees
23 Feb - 24 Feb
SPACIOUS LUXURY- PARTY BARN… PL TBl, PNG PNG, ARCADE, PATIOS. ACCESS TO POOLS!

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

9.6 out of 10, Exceptional, (51)
"Our large family had a great stay here! There was something for everyone to do! "
The price is AU$706
includes taxes & fees
18 Feb - 19 Feb
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

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

9.4 out of 10, Exceptional, (46)
"Everything was great and really fun!"
The price is AU$1,075
includes taxes & fees
18 Feb - 19 Feb
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

Spacious and clean 4-bedroom townhome in Urbandale with fitness room, WiFi

10.0 out of 10, Exceptional, (1)
"Very welcoming house and very spacious "
Spacious and clean 4-bedroom townhome in Urbandale with fitness room, WiFi

2-bedroom vacation home just 3 minutes drive to Drake University

9.8 out of 10, Exceptional, (29)
"My husband and I grew up and lived in this part of town and our children and friends still live there, so the location was perfect. The space was great and everything was clean and well cared for. The only negative is the driveway-there are planters that prevent you from turning around to exit the property easilyand you have to back out a narrow strip of driveway. I would recommend moving those large planters (at least in the winter) for an easier exit. Other than that, it was great!"
2-bedroom vacation home just 3 minutes drive to Drake University

Comfortable and Spacious 3 Bedroom Home

9.8 out of 10, Exceptional, (36)
"We were in town for a funeral and the location of the property was perfect for our location of activities. House was good in person, as advertised in the pictures. "
Comfortable and Spacious 3 Bedroom Home

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

9.8 out of 10, Exceptional, (47)
"This property was perfect for our family christmas- plenty of things on the property for everyone to do, and close proximity to so many options for all ages"
The price is AU$1,102
includes taxes & fees
18 Feb - 19 Feb
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

Hot Tub, Fenced Yard, Games, Office/Gym + Pets Ok!

9.4 out of 10, Exceptional, (22)
"This property was the best VRBO we've ever stayed at.so far.We came to town for the holidays and found the house comfortable, with plenty of room to relax between gatherings. Every bedroom has a TV, plenty of pillows, room for your things, and a comfortable bed. The only drawback to the house was the stairs. There are stairs everywhere. We will definitely book this house again. As long as no one is on crutches. "
Hot Tub, Fenced Yard, Games, Office/Gym + Pets Ok!

Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

10.0 out of 10, Exceptional, (24)
"We came to Des Moines to put on a baby shower. This house was perfect for our family!! Our host communicated with us before, during and after our stay. The house was exactly as described. So many extra touches throughout the entire house. We highly recommend! "
The price is AU$852
includes taxes & fees
18 Feb - 19 Feb
Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

Suburban Oasis with Hot Tub Spa

10.0 out of 10, Exceptional, (14)
"The home was inviting, clean, and the check in and check out process were smooth. I’d definitely recommend this place to others and would stay here again. Thanks for being a great host!! "
Suburban Oasis with Hot Tub Spa

Luxury 4 bedroom and 2.5 bath home

9.0 out of 10, Wonderful, (10)
"We were in town for my mom’s funeral. It was nice that my kids and grandkids could all stay together. Location was great, beds comfortable and nice to have 2.5 bathrooms. Would stay again."
The price is AU$811
includes taxes & fees
18 Feb - 19 Feb
Luxury 4 bedroom and 2.5 bath home

Beautiful Rustic Barn just waiting for you to kick back and relax.

10.0 out of 10, Exceptional, (393)
"My husband and I were looking for a place a few hours from home for a weekend away. This was perfect! Quiet and relaxing- beautiful property! We went to Osceola for dinner at the Iron Horse, and back the next evening for live music and BBQ at Revelton. Would absolutely stay again!"
The price is AU$301
includes taxes & fees
18 Feb - 19 Feb
Beautiful Rustic Barn just waiting for you to kick back and relax.

The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14

10.0 out of 10, Exceptional, (17)
"Three families came together to enjoy a couple days of togetherness here, and we couldn't have asked for better accommodations. So cozy and comfortable! Hot tub, huge dining room table, game zone, well stocked kitcgen and comfy beds were favorites. Definitely recommend!!"
The price is AU$609
includes taxes & fees
2 Mar - 3 Mar
The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14

Good Vibes 2 Bed Home Centrally Located on Quiet St.

10.0 out of 10, Exceptional, (35)
"Nicely decorated & Clean property. Bathroom needs newer tub surround. Hooks for hanging clothes, towels, & coats, which was nice. Quiet neighborhood. We would stay here again."
Good Vibes 2 Bed Home Centrally Located on Quiet St.

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

10.0 out of 10, Exceptional, (21)
"Very quiet location just out of town. Lots of space inside and out. Great hosts. "
Raccoon River Retreat: Indoor Pool & Outdoor Fun!

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

10.0 out of 10, Exceptional, (55)
"Stayed 4 nights in town for our daughter’s wedding. Great location. Very nice and clean property. Everything went very smoothly. Highly recommend."
The price is AU$543
includes taxes & fees
18 Feb - 19 Feb
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

Serenity Heights - VALENTINE SPECIAL!!! Super low prices in February!

10.0 out of 10, Exceptional, (73)
"Just what we were looking for! Property was beautiful, house was clean, hosts were great and easy to work with."
The price is AU$550
includes taxes & fees
1 Mar - 2 Mar
Serenity Heights - VALENTINE SPECIAL!!! Super low prices in February!
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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Other types of properties in Winterset you may be interested in

Covered Bridge Inn

2.5 star property
9.2 out of 10, Wonderful, (649)
"Good. Recommend."
The price is AU$102
includes taxes & fees
18 Feb - 19 Feb
Covered Bridge Inn

Cobblestone Inn & Suites - Winterset, IA

2.5 star property
9.2 out of 10, Wonderful, (607)
"This hotel was amazing. All staff welcome you with a smile and help with any detail. The room was very cozy as well. Breakfast eggs were cold already at 7:15 or so but the food itself tasted great. Winterset ,the surroundings and the people here are so calm and inviting."
The price is AU$194
includes taxes & fees
26 Feb - 27 Feb
Cobblestone Inn & Suites - Winterset, IA

Stoney Creek Hotel Des Moines - Johnston

2.5 star property
9.0 out of 10, Wonderful, (1592)
"Amazing"
The price is AU$163
includes taxes & fees
20 Feb - 21 Feb
Stoney Creek Hotel Des Moines - Johnston
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.

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 3 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 Clark Tower 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.