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Winterset Holiday Rentals

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Holiday Rentals in Winterset

Terrace/patio
PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!
9.8 out of 10, Exceptional, (32)
"The property itself was very clean and beautiful. We enjoyed our time and stay. The party barn and playset outside the kids really enjoyed. Us adults spent a lot of time in the hot tub. We are planning on renting another property of steven's at the end of the month. Overall experience was 5 stars in our eyes"
The price is NZ$1,292
includes taxes & fees
28 May - 29 May
PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!
Interior
SO MICH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
9.4 out of 10, Exceptional, (25)
"Wonderful house with plenty of space and activities for our competitive friend group! We 100% recommend and will book again in the future!"
The price is NZ$1,036
includes taxes & fees
28 May - 29 May
SO MICH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Fridge, microwave, oven, stovetop
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
9.6 out of 10, Exceptional, (27)
"This property has a great location. Lots of games for kids in basement. Clean."
The price is NZ$931
includes taxes & fees
27 May - 28 May
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
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Smart TV, video games, ping pong
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!
9.8 out of 10, Exceptional, (27)
"Great place and host! Only slight downfall was the outdoor trash cans were very full and very smelly. Also the yard had not been mowed all year which was just a small inconvenience when playing yard games. But overall a very fun and good experience!"
The price is NZ$829
includes taxes & fees
27 May - 28 May
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!
Bathtub, hair dryer, towels, soap
Comfortable and Spacious 3 Bedroom Home
9.6 out of 10, Exceptional, (21)
"Everything was great in this quiet neighborhood. The house was cozy and very welcoming. Loved that there was plenty of towels and all the bath toiletries provided was a plus. There was coffee/hot chocolate pods provided which was nice plus since they are not always offered. The deck area with table and chairs was really nice(although the deck could have used a little tidying up)."
Comfortable and Spacious 3 Bedroom Home
Fridge, microwave, oven, stovetop
6212 Boston Avenue · 3 bdr / 1 bath Fully Remodeled House off Merle Hay
9.8 out of 10, Exceptional, (19)
"Clean property, well maintained and accurately portrayed on the website. Highly recommend for couples or family."
6212 Boston Avenue · 3 bdr / 1 bath Fully Remodeled House off Merle Hay
Exterior
Beautiful Rustic Barn just waiting for you to kick back and relax.
10.0 out of 10, Exceptional, (378)
"Convenient"
The price is NZ$311
includes taxes & fees
28 May - 29 May
Beautiful Rustic Barn just waiting for you to kick back and relax.
Fridge, microwave, oven, stovetop
Good Vibes 2 Bed Home Centrally Located on Quiet St.
9.8 out of 10, Exceptional, (22)
"This was perfect for what we needed!"
Good Vibes 2 Bed Home Centrally Located on Quiet St.
Fridge, microwave, oven, stovetop
Lovely 2-bedroom apartment in Sherman Hill-4
10.0 out of 10, Exceptional, (3)
"Simply put great stay"
The price is NZ$287
includes taxes & fees
27 May - 28 May
Lovely 2-bedroom apartment in Sherman Hill-4
Golf
Quiet Studio on Grand - Downtown DSM!
8.0 out of 10, Very good, (4)
"Nice cute little studio close to downtown Des Moines. Good communication from the host and easy check in and out."
The price is NZ$278
includes taxes & fees
27 May - 28 May
Quiet Studio on Grand - Downtown DSM!
Outdoor dining
Spacious updated home minutes from Airport and DT!
7.8 out of 10, Good, (7)
"We were in Des Moines for state wrestling and it was nice to come back to a comfortable, quiet spot to regroup. Lots of space and the host was quick to answer any questions."
The price is NZ$537
includes taxes & fees
27 May - 28 May
Spacious updated home minutes from Airport and DT!
Property grounds
Gorgeous Home With Sauna Sleeps 7
9.6 out of 10, Exceptional, (28)
"Nice cozy place where famkly could all be together."
Gorgeous Home With Sauna Sleeps 7
Fridge, microwave, oven, stovetop
Perfect Big Groups~Downtown~Fun Backyard~Pet Frdly
6.4 out of 10, (6)
"Let me start by saying that the property manager Tobias was a good communicator. We had our family Christmas reunion here. The 3 units worked out well for our out of town families to stay. This is an old place that still needs repairs here & there but what house over 100 years old doesn’t. I’m sure it was grand in its early days. I’m happy that the owners have plans for repairs & more updating because I hate to see old homes get run down. There was a leak under one of the kitchen sinks. The...
Perfect Big Groups~Downtown~Fun Backyard~Pet Frdly
Property grounds
Casa Mackie - Sophisticated Split Level, 5 Bedroom, 3 Bathroom
10.0 out of 10, Exceptional, (6)
"We were in town for a 10u baseball tournament. 4 parents and 2 ball players. Worked perfectly!"
Casa Mackie - Sophisticated Split Level, 5 Bedroom, 3 Bathroom
Fridge, microwave, oven, stovetop
Luxurious New Apartment with Gym and Social Room
10.0 out of 10, Exceptional, (9)
"Clean and comfortable place."
The price is NZ$289
includes taxes & fees
3 Jun - 4 Jun
Luxurious New Apartment with Gym and Social Room
Free WiFi, bed sheets
Studio Sleeps 4 - Next to 3 Breweries!
10.0 out of 10, Exceptional, (1)
"Nice little appointment, we were just there to sleep really quite at night seemed like a nice neighborhood."
The price is NZ$278
includes taxes & fees
27 May - 28 May
Studio Sleeps 4 - Next to 3 Breweries!
Fridge, microwave, oven, stovetop
Charming 4BR/2BA in central DSM
10.0 out of 10, Exceptional, (14)
"Close to Drake Neighborhood and other restaurants and amenities. Easy to find and get into. Accommodated 10 people (6 adults and 4 kids) Great location and size for what we needed."
The price is NZ$487
includes taxes & fees
23 Jun - 24 Jun
Charming 4BR/2BA in central DSM
Exterior
Charming 4 Bedroom Home With Beautiful Backyard
9.4 out of 10, Exceptional, (45)
"Very clean home in a beautiful historic neighborhood. Easy access to highway and interstate. I highly recommend this home and would stay here again myself."
Charming 4 Bedroom Home With Beautiful Backyard
Smart TV, books
Stylish Split Foyer - The Sullivan 4 Bedrooms | 2 Bathrooms
9.8 out of 10, Exceptional, (22)
"Exactly as described and well worth the value"
Stylish Split Foyer - The Sullivan 4 Bedrooms | 2 Bathrooms
Interior
✧Odyssey at Keystone | Elegant 1BD Apartment✧
9.6 out of 10, Exceptional, (4)
"The location was perfect, right off the interstate and centrally located between everywhere we wanted to be. Very Modern style apartment but able to feel like home and still sit back and watch TV. The washer and dryer in the apartment made it very easy to head home and not have to dread doing all the laundry. Definitely will be staying here again!"
✧Odyssey at Keystone | Elegant 1BD Apartment✧
Don't see what you're looking for?
See all available properties in Winterset
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.

Other types of properties in Winterset you may be interested in

Property entrance
Covered Bridge Inn
2.5 star property
9.4 out of 10, Exceptional, (573)
"The room was very comfortable and the staff was very welcoming "
The price is NZ$142
includes taxes & fees
27 May - 28 May
Covered Bridge Inn
Lobby
Cobblestone Inn & Suites - Winterset, IA
2.5 star property
9.2 out of 10, Wonderful, (534)
"Great facility and wonderful staff"
The price is NZ$186
includes taxes & fees
9 Jun - 10 Jun
Cobblestone Inn & Suites - Winterset, IA
Indoor spa tub
Stoney Creek Hotel Des Moines - Johnston
2.5 star property
8.8 out of 10, Excellent, (1178)
"Every staff person we encountered was so nice and helpful! The amenities were amazing and the pool is great! Breakfast was awesome with many choices including freshly made pancakes!"
The price is NZ$181
includes taxes & fees
27 May - 28 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winterset holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winterset. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winterset. Seeing all the best attractions is bound to make you fall in love with Winterset. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winterset short-term rentals, that won’t be hard to do.

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?

PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!: This holiday home rental outside of Winterset offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 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, Roseman Bridge and Madison County Courthouse 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.

Recent reviews of Winterset properties
Expedia verified reviews