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Winterset Holiday Rentals

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Holiday Rentals in Winterset

SO MICH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
9.4 out of 10, Exceptional, 26 reviews
"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$1,235
per night
12 Jun - 13 Jun
SO MICH 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!
9.6 out of 10, Exceptional, 27 reviews
"This property has a great location. Lots of games for kids in basement. Clean."
The price is NZ$1,130
per night
11 Jun - 12 Jun
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!
9.8 out of 10, Exceptional, 33 reviews
"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$1,498
per night
17 Jun - 18 Jun
PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!
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Lovely 2-bedroom apartment in Sherman Hill-4
10.0 out of 10, Exceptional, 3 reviews
"Simply put great stay"
The price is NZ$283
per night
7 Jul - 8 Jul
Lovely 2-bedroom apartment in Sherman Hill-4
6212 Boston Avenue · 3 bdr / 1 bath Fully Remodeled House off Merle Hay
10.0 out of 10, Exceptional, 21 reviews
"The house matched the description provided and met our expectations. The fenced in backyard was great for our dog. Amenities met our needs for the three days we were there. The neighborhood was great, everyone was friendly. Would recommend to anyone who needs a place to crash and doesn't want to stay at a hotel!"
The price is NZ$396
per night
10 Jun - 11 Jun
6212 Boston Avenue · 3 bdr / 1 bath Fully Remodeled House off Merle Hay
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!
9.8 out of 10, Exceptional, 28 reviews
"Reading gathering place for our family"
The price is NZ$821
per night
9 Jun - 10 Jun
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!
Beautiful Rustic Barn just waiting for you to kick back and relax.
10.0 out of 10, Exceptional, 379 reviews
"Great Place!"
The price is NZ$308
per night
11 Jun - 12 Jun
Beautiful Rustic Barn just waiting for you to kick back and relax.
✧Odyssey at Keystone | Elegant 1BD Apartment✧
9.6 out of 10, Exceptional, 4 reviews
"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✧
Comfortable and Spacious 3 Bedroom Home
9.6 out of 10, Exceptional, 21 reviews
"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
Stylish Oasis for Unforgettable Getaways
Stylish Oasis for Unforgettable Getaways
Luxurious New Apartment with Gym and Social Room
10.0 out of 10, Exceptional, 9 reviews
"Clean and comfortable place."
The price is NZ$286
per night
11 Jun - 12 Jun
Luxurious New Apartment with Gym and Social Room
Quiet Studio on Grand - Downtown DSM!
8.4 out of 10, Very good, 5 reviews
"Though I messaged the manager, I never heard back. Also, there was no hot water"
The price is NZ$275
per night
13 Jun - 14 Jun
Quiet Studio on Grand - Downtown DSM!
Spacious updated home minutes from Airport and DT!
8.0 out of 10, Very good, 8 reviews
"If you want to be close to downtown DSM, but want a more relaxing stay, I’d definitely consider this property! The house was very clean, and there is a great deck with a backyard for relaxing!"
The price is NZ$531
per night
12 Jun - 13 Jun
Spacious updated home minutes from Airport and DT!
Studio Sleeps 4 - Next to 3 Breweries!
10.0 out of 10, Exceptional, 1 review
"Nice little appointment, we were just there to sleep really quite at night seemed like a nice neighborhood."
The price is NZ$275
per night
11 Jun - 12 Jun
Studio Sleeps 4 - Next to 3 Breweries!
3 BR for 9 Guests -Large Beautiful 3 Story Duplex
The price is NZ$533
per night
7 Jul - 8 Jul
3 BR for 9 Guests -Large Beautiful 3 Story Duplex
Good Vibes 2 Bed Home Centrally Located on Quiet St.
9.8 out of 10, Exceptional, 23 reviews
"This was perfect for what we needed!"
Good Vibes 2 Bed Home Centrally Located on Quiet St.
Stylish Split Foyer - The Sullivan 4 Bedrooms | 2 Bathrooms
9.8 out of 10, Exceptional, 22 reviews
"Exactly as described and well worth the value"
Stylish Split Foyer - The Sullivan 4 Bedrooms | 2 Bathrooms
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines
9.4 out of 10, Exceptional, 149 reviews
"This property was a perfect place for my family to stay and friends too! All the history that is shown in that home was breathtaking! All the rooms were clean and ready for us! A great game room and bedrooms that were unique in their own ways!"
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines
Bold Edgy /Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
9.6 out of 10, Exceptional, 5 reviews
"The host was great! The check in instructions were very helpful in finding the garage that was for our use while staying at this rental. We had one request and the host took care of this request. The location is close to shopping and restaurants. Will definitely use this rental if in Des Moines again."
The price is NZ$372
per night
11 Jun - 12 Jun
Bold Edgy /Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed
Gem in West Dsm | 4BD/3BA Home | Perfect Location
9.6 out of 10, Exceptional, 5 reviews
"We had 8 adults and 2 children staying for the weekend. Everyone had their own space and was comfortable. Beds were surprisingly comfortable and plenty of linens for our needs. Location of the property was near perfect for everything we had planned. If you have kids or pets, the yard leaves quite a bit to be desired. A little upkeep there and all's good. Daniel was "Johnny on the Spot" with communication so no issues there. Clean dishes were left in the dishwasher when we arrived and we...
Gem in West Dsm | 4BD/3BA Home | Perfect Location
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

Covered Bridge Inn
2.5 star property
9.4 out of 10, Exceptional, 577 reviews
"We arrived over an hour before check in. The gentleman who greeted us was very pleasant and accommodating and checked us right in. Our room is very comfortable and super clean. It is slightly dated. There is only one plug available to charge our phones. The bathroom fan was super loud. However, the cleanliness of the room, comfort of the bed and pleasantness of the staff overcome the slight negatives of our stay. "
The price is NZ$140
per night
16 Jun - 17 Jun
Covered Bridge Inn
Cobblestone Inn & Suites - Winterset, IA
2.5 star property
9.2 out of 10, Wonderful, 536 reviews
"Clean quiet. Step up from the norm. Nice lounge and friendly staff. Thank you"
The price is NZ$184
per night
7 Jul - 8 Jul
Cobblestone Inn & Suites - Winterset, IA
Stoney Creek Hotel Des Moines - Johnston
2.5 star property
8.8 out of 10, Excellent, 1,216 reviews
"Enjoyed the cabin like feel."
The price is NZ$214
per night
9 Jun - 10 Jun
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