Winterset Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Winterset holiday rentals

Outdoor dining

Holiday Home in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
10.0 out of 10, Exceptional, (5 reviews)
"The house was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!"
United States
Heather G.
The price is HK$834
HK$2,603 total
includes taxes & fees
2 Feb - 3 Feb
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Drake

Sleepover | Attractive Studio and Gym - Des Moines
10.0 out of 10, Exceptional, (2 reviews)
"Clean and quiet for our stay. "
United States
Jackie
The price is HK$506
HK$1,523 total
includes taxes & fees
29 Jan - 30 Jan
Sleepover | Attractive Studio and Gym - Des Moines
2 bedrooms, iron/ironing board, WiFi, bed sheets

Cottage in Woodland Heights

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
10.0 out of 10, Exceptional, (3 reviews)
"Great location with a cozy, clean, pet-friendly cottage. Had everything we needed. Will stay here again."
United States
Jeff C.
The price is HK$555
HK$1,626 total
includes taxes & fees
30 Jan - 31 Jan
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Exterior

Cabin in Osceola

Cozy pond house nestled in nature waiting for you to enjoy
10.0 out of 10, Exceptional, (1 review)
"This was our first stay at a place like this. It was an incredibly relaxing stay. Host was very responsive even before our stay with any questions. I plan to come back! "
United States
Kristy A.
The price is HK$819
HK$1,310 total
includes taxes & fees
29 Jan - 30 Jan
Cozy pond house nestled in nature waiting for you to enjoy
Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Drake

Sleepover | Impressive Studio and Gym - Des Moines
10.0 out of 10, Exceptional, (2 reviews)
"The place was located right next door to Drake which made doing a campus visit easily walkable and so were restaurants. Found parking on the street nearby and didn’t have to move the car until checkout. "
United States
Thomas
The price is HK$506
HK$1,413 total
includes taxes & fees
1 Feb - 2 Feb
Sleepover | Impressive Studio and Gym - Des Moines
Smart TV

Holiday Home in Indianola

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
9.4 out of 10, Exceptional, (18 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is HK$780
HK$1,870 total
includes taxes & fees
29 Jan - 30 Jan
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Terrace/patio

Apartment in Woodland Heights

Sleepover | Private 1BD/1BA - Downtown Des Moines
8.0 out of 10, Very good, (1 review)
"Newer apartment complex close to downtown. The space was clean and we felt safe in our surroundings. Positives: It was bigger than the basic hotel and cheaper so we were happy with our stay. Once we found the pool/game room on the 3rd floor, we enjoyed. Appreciated the hangers in the closet and ice trays in the freezer. Cons: No private patio, the couch is actually a futon and uncomfortable, the street parking was about 2 blocks away each night and the TV connection was painfully slow; we ended...
United States
M R.
The price is HK$592
HK$1,511 total
includes taxes & fees
29 Jan - 30 Jan
Sleepover | Private 1BD/1BA - Downtown Des Moines
Terrace/patio

Apartment in Woodland Heights

Sleepover | Prime 1BD/1BA - Downtown Des Moines
8.8 out of 10, Excellent, (3 reviews)
"The place was nice and we rented it just as a get away for a night so we cpuld go swimming. The pool sign said closed at 8 pm. So we ate dinner at the restaurant downstairs and then just went back home. Pool closed at 8 and opened at 10 am..... nit very long of access when chek in is at 4pm. Also, you have to know the combo to get in the building and find the key in the appropriate place. Not hard.... just annoying...."
United States
Christina B.
The price is HK$678
HK$1,608 total
includes taxes & fees
1 Feb - 2 Feb
Sleepover | Prime 1BD/1BA - Downtown Des Moines
Terrace/patio

Apartment in Woodland Heights

Sleepover | Charming 1BD/1BA - Downtown Des Moines
10.0 out of 10, Exceptional, (1 review)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
The price is HK$678
HK$1,608 total
includes taxes & fees
22 Feb - 23 Feb
Sleepover | Charming 1BD/1BA - Downtown Des Moines
Smart TV

Apartment in West Des Moines

Historic Valley Junction Loft
9.8 out of 10, Exceptional, (21 reviews)
"Great location, clean and comfy place. The location is charming, with a number of shops and restaurants next door. Would definitely stay here again. "
United States
Rebecca S.
The price is HK$614
HK$1,081 total
includes taxes & fees
29 Jan - 30 Jan
Historic Valley Junction Loft
Property grounds

Holiday Home in NEW VIRGINIA

Beautiful Rustic Barn just waiting for you to kick back and relax.
10.0 out of 10, Exceptional, (406 reviews)
"Amazing property "
United States
Anonymous traveller
The price is HK$852
HK$1,427 total
includes taxes & fees
10 Feb - 11 Feb
Beautiful Rustic Barn just waiting for you to kick back and relax.
Fridge, microwave, oven, stovetop

Holiday Home in Indianola

The Hen House Country Living with Farm Life Appeal Indianola, IA
10.0 out of 10, Exceptional, (9 reviews)
"Lori and Les make you feel right at home. They go above and beyond to ensure you have everything you could need and more. The farm is so peaceful and watching the animals is entertaining."
United States
Valerie
The price is HK$1,053
HK$1,474 total
includes taxes & fees
31 Jan - 1 Feb
The Hen House Country Living with Farm Life Appeal Indianola, IA
Exterior

Holiday Home in Drake

Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly
10.0 out of 10, Exceptional, (1 review)
"It was well organized and clean. The on site parking was super convenient. Host was very response, which I really appreciated. Would stay here again!"
United States
Elvis G.
The price is HK$515
HK$1,581 total
includes taxes & fees
29 Jan - 30 Jan
Near Downtown ~ 2BDR & Fun Backyard ~ Pet Friendly
Fridge, microwave, oven, stovetop

Apartment in Waukee

Brand New 1 Bedroom, Gym, Social Room, Balcony
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and convenient. "
United States
ronald s.
The price is HK$730
HK$1,386 total
includes taxes & fees
30 Jan - 31 Jan
Brand New 1 Bedroom, Gym, Social Room, Balcony
Property grounds

Holiday Home in Dallas Center

Farmhouse Oasis
10.0 out of 10, Exceptional, (21 reviews)
"This place was amazing. The host was so helpful and made us feel right at home. The hot tub was easily accessible! Everything was perfect and would definitely stay here again. "
United States
Naomi
The price is HK$639
HK$1,244 total
includes taxes & fees
29 Jan - 30 Jan
Farmhouse Oasis
Interior

Holiday Home in Urbandale

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
9.4 out of 10, Exceptional, (75 reviews)
"Loved the stay just wish the pool was on site, overall no complaints "
United States
Arika R.
The price is HK$695
HK$2,875 total
includes taxes & fees
1 Feb - 2 Feb
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Outdoor dining

Holiday Home in Woodland Heights

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
10.0 out of 10, Exceptional, (68 reviews)
"Nice place, well kept. We enjoyed going out downtown. "
United States
Amber B.
The price is HK$860
HK$2,553 total
includes taxes & fees
1 Feb - 2 Feb
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Desk, iron/ironing board, free WiFi, bed sheets

Apartment in West Des Moines

Sleepover | Marvelous 1BD/1BA - Des Moines
10.0 out of 10, Exceptional, (4 reviews)
"We stayed at the Flux apartments in downtown. Our accommodation was exceptional in all respects. Thank you for your hospitality!"
United States
Miriam G.
The price is HK$592
HK$1,510 total
includes taxes & fees
29 Jan - 30 Jan
Sleepover | Marvelous 1BD/1BA - Des Moines
Exterior

Holiday Home in Des Moines

Beautiful home minutes from downtown!
9.4 out of 10, Exceptional, (27 reviews)
"What a great place to stay! "
United States
Annie P.
The price is HK$912
HK$2,140 total
includes taxes & fees
3 Feb - 4 Feb
Beautiful home minutes from downtown!
Interior

Apartment in Downtown Des Moines

2BR 2 BA Apt Downtown w/Hot Tub & Amenities!
9.0 out of 10, Wonderful, (4 reviews)
"Very Clean. Perfect downtown location. The number of walkable restaurants were outstanding. Highly recommend brunch at Americana and dinner at Exile. "
United States
Jeanne C.
2BR 2 BA Apt Downtown w/Hot Tub & Amenities!
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

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

10/10 Excellent
"Clean place. Great location. Staff was helpful."
CHRISTOPHER 1-night trip
Posted 3 days ago
Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

Find out more about Winterset

Search for holiday rentals in Winterset on Expedia! You can easily find your home rentals, villas, holiday apartments in Winterset using one of the methods below:

  • View our selection of featured holiday rentals in Winterset
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  • Enter your travel dates to view the best deals on holiday rentals in Winterset while they last

Look no further and take a look at our great range of rental properties in Winterset!

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 5 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, Clark Tower 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.