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Winterset Holiday Rentals

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Holiday Rentals in Winterset

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

9.8 out of 10, Exceptional, (42)
"Beautiful house, plenty of beds to accommodate everyone & the basement game room was a hit. Something for everyone, ages 15-62."
The price is AU$1,033
includes taxes & fees
5 Jan - 6 Jan 2025
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

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

9.6 out of 10, Exceptional, (47)
"Our large group of 8 adults and 5 kids had tons of fun in the game room! Kids spent the entire time there. So much fun and things to do in that space! There are lots of beds and they were pretty comfortable. The kitchen is pretty small with minimal counter space and lacking in supplies. The bathroom setup is a little misleading, there is a full bath upstairs, tiny sink & toilet on the main floor and a shower and sink only in the basement which smells super damp and musty. One awesome feature is...
The price is AU$820
includes taxes & fees
30 Dec - 31 Dec
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

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

10.0 out of 10, Exceptional, (31)
"Very spacious home close to many amenities! Highly recommend!"
Executive Living 2min to Jordan Creek 6 bed/5 bath near Jordan Creek Mall!

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

10.0 out of 10, Exceptional, (51)
"This property lived up to its VRBO listing and reviews. It is clean,spacious, well-appointed, and well-stocked with everything from coffee to toothpaste. We had no problems at all. The party barn was perfect for a day after our son's wedding get-together. SO much fun! We would definitely rent again!"
The price is AU$1,483
includes taxes & fees
5 Jan - 6 Jan 2025
SPACIOUS LUXURY- PARTY BARN… PL TBl, PNG PNG, ARCADE, PATIOS. ACCESS TO POOLS!

Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom

10.0 out of 10, Exceptional, (11)
"Large modern house, great space both inside and out. Nice fixtures and fittings (couple of minor things need a touch up) but overall wonderful! Comfy living room, beds comfy too. Garden and decking area great space to relax in. Host friendly and super responsive....also able to accommodate extra nights stay."
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom

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

9.4 out of 10, Exceptional, (42)
"Worked great for us. Plenty of beds for everyone, held a couple day meeting. Close to restaurants and easy to get too. "
The price is AU$1,237
includes taxes & fees
25 Dec - 26 Dec
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

Comfortable and Spacious 3 Bedroom Home

9.6 out of 10, Exceptional, (34)
"Visiting family for Thanksgiving and this home worked out very well for us. Comfortable stay."
Comfortable and Spacious 3 Bedroom Home

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

9.4 out of 10, Exceptional, (19)
"Easy check-in and access. Great neighborhood. Plenty of parking. Lovely accommodations. Loads of space. Fun extras like fireplace and hot tub. Perfect for our lady’s weekend. 10/10. Highly recommend. "
The price is AU$610
includes taxes & fees
29 Dec - 30 Dec
Hot Tub, BBQ, Fenced Yard, Games, Office/Gym + Pets Ok!

Gem in West Dsm | 4BD/3BA Home | Perfect Location

9.8 out of 10, Exceptional, (18)
"This house is in a great location and very nice. It was a great place for a girls weekend away for shopping. My only comment would be we didn't have the 6 chairs at the table like we expected. Great host!"
Gem in West Dsm | 4BD/3BA Home | Perfect Location

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

10.0 out of 10, Exceptional, (21)
"We were meeting with extended family for Thanksgiving and need a place for 9 people (3 generations) to stay -- and this one delivered! The house was clean and beautifully furnished. The host was friendly and responded quickly to my questions. The kitchen was outfitted with everything we needed for meals and included the fixings for coffee and tea. Best of all, with five bedrooms, all 9 of us (3 generations) could stay in one place. The laundry facilities were a bonus! The location made it easy...
The price is AU$777
includes taxes & fees
26 Dec - 27 Dec
Family-Friendly Home Near Airport and Downtown with Plenty of Quality Amenities

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

9.4 out of 10, Exceptional, (158)
"The house was amazing- so many conversation pieces. We played games, watched movies and enjoyed the overall comfort of this home. Beds were very comfortable- bathrooms well stocked and clean!! Parking is great!!!! Highly recommend!!!"
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines

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

9.8 out of 10, Exceptional, (15)
"We had nice relaxing stay. Watched movies In the theater area and relaxed in the hot tub. Definitely be going back"
The price is AU$791
includes taxes & fees
24 Dec - 25 Dec
Close to Drake/Downtown - Filled With Amenities, Pet Friendly, Hot Tub, Theater!

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$414
includes taxes & fees
26 Dec - 27 Dec
Downtown Skyline Views in Modern Townhome with Rooftop Patios

Quiet Studio on Grand - Downtown DSM!

6.6 out of 10, (7)
"Though I messaged the manager, I never heard back. Also, there was no hot water"
Quiet Studio on Grand - Downtown DSM!

Gorgeous Home With Sauna Sleeps 7

9.6 out of 10, Exceptional, (35)
"A good place to stay with a larger group. An old home on a busy street, but clean with a nice kitchen. Worked great for our family and friends. "
Gorgeous Home With Sauna Sleeps 7

Studio Sleeps 4 - Next to 3 Breweries!

8.8 out of 10, Excellent, (11)
"Great"
The price is AU$230
includes taxes & fees
5 Jan - 6 Jan 2025
Studio Sleeps 4 - Next to 3 Breweries!

Charming 4 Bedroom Home With Beautiful Backyard

9.2 out of 10, Wonderful, (57)
"Excellent location, "bigger on the inside" house. The only drawback is there's only one bathroom, but it wasn't an issue since I was only staying with one other person. I would definitely stay here again."
Charming 4 Bedroom Home With Beautiful Backyard

Roomy 4BR by Drake Sleeps 13 HUGE yard

8.0 out of 10, Very good, (3)
"A little hiccup with check in process and email. Otherwise it went very smooth. Would have liked the screen on front door fixed."
The price is AU$428
includes taxes & fees
5 Jan - 6 Jan 2025
Roomy 4BR by Drake Sleeps 13 HUGE yard

The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

9.8 out of 10, Exceptional, (17)
"This is a very well-stocked and comfortable place to stay, and the owner does a fantastic job of communicating and answering questions. My only critique is that it would be nice to have more than one key and fob so that we could leave the building in separate groups without worrying about how to get back in. Also, a remote for the garage door opener would be highly convenient but isn't strictly necessary. "
The price is AU$341
includes taxes & fees
24 Dec - 25 Dec
The Carmel/Bold/Massage /Chair Spacious / 3D Wall / Pool / Gym / Tanning Bed

Close to Downtown~Fun Backyard~Pet Friendly~2 BDRM

8.6 out of 10, Excellent, (28)
"Great location, easy on easy off highway and near Drake."
Close to Downtown~Fun Backyard~Pet Friendly~2 BDRM
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

Cobblestone Inn & Suites - Winterset, IA

2.5 star property
9.2 out of 10, Wonderful, (601)
"Great customer service "
The price is AU$161
includes taxes & fees
8 Jan - 9 Jan 2025
Cobblestone Inn & Suites - Winterset, IA

Covered Bridge Inn

2.5 star property
9.2 out of 10, Wonderful, (642)
"Very delightful gentlemen completed the check-in quickly and cheerfully!"
The price is AU$104
includes taxes & fees
24 Dec - 25 Dec
Covered Bridge Inn

Days Inn by Wyndham West Des Moines / Clive

2.0 star property
5.8 out of 10, (1003)
"Excellent price and very clean facility with friendly staff no matter what the hour. "
The price is AU$84
includes taxes & fees
26 Dec - 27 Dec
Days Inn by Wyndham West Des Moines / Clive
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?

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!: This holiday home rental outside of Winterset offers a patio, a selection of games 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. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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, Holliwell Bridge and Roseman 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.