Holiday Rentals in Winterset

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Our top choices for Winterset holiday rentals

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
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.
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Sleepover | Attractive Studio and Gym - Des Moines

Sleepover | Attractive Studio and Gym - Des Moines
Drake
10.0 out of 10, Exceptional, (2 reviews)
"Clean and quiet for our stay. "
United States
Jackie
The price is €169
includes taxes & fees
8 Feb - 9 Feb
Sleepover | Attractive Studio and Gym - Des Moines

2 BR Dwntwn Apt with Hot Tub

2 BR Dwntwn Apt with Hot Tub
Downtown Des Moines
9.0 out of 10, Wonderful, (9 reviews)
"Very nice apartment! Clean with close parking. All questions/concerns were answered quickly. Did everything we needed it to do! "
United States
Dawn C.
The price is €850
includes taxes & fees
8 Feb - 9 Feb
2 BR Dwntwn Apt with Hot Tub

Sleepover | Impressive Studio and Gym - Des Moines

Sleepover | Impressive Studio and Gym - Des Moines
Drake
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 €157
includes taxes & fees
8 Feb - 9 Feb
Sleepover | Impressive Studio and Gym - Des Moines

Historic Valley Junction Loft

Historic Valley Junction Loft
West Des Moines
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 €144
includes taxes & fees
8 Mar - 9 Mar
Historic Valley Junction Loft

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Woodland Heights
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 €190
includes taxes & fees
10 Feb - 11 Feb
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
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 €146
includes taxes & fees
7 Feb - 8 Feb
Cozy pond house nestled in nature waiting for you to enjoy

Lovely 2-bedroom apartment in Sherman Hill-4

Lovely 2-bedroom apartment in Sherman Hill-4
Downtown Des Moines
8.4 out of 10, Very good, (18 reviews)
"Great place for overnight stay! Clean and parking was easy. Upstairs neighbors were a little loud, but other than that it was a great place to stay after our concert."
United States
ADRIENNE C.
The price is €111
includes taxes & fees
8 Feb - 9 Feb
Lovely 2-bedroom apartment in Sherman Hill-4

Quiet Studio on Grand Near Hospitals!

Quiet Studio on Grand Near Hospitals!
Downtown Des Moines
8.6 out of 10, Excellent, (10 reviews)
"Pretty nice spot"
United States
Alberto P.
Quiet Studio on Grand Near Hospitals!

Nice 2 bedroom in Sherman Hill-8

Nice 2 bedroom in Sherman Hill-8
Downtown Des Moines
9.2 out of 10, Wonderful, (21 reviews)
"Nice location "
United States
Allen E.
Nice 2 bedroom in Sherman Hill-8

Sleepover | Charming 1BD/1BA - Downtown Des Moines

Sleepover | Charming 1BD/1BA - Downtown Des Moines
Woodland Heights
10.0 out of 10, Exceptional, (1 review)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
Sleepover | Charming 1BD/1BA - Downtown Des Moines

Sleepover | Wonderful 1BD/1BA -Downtown Des Moines

Sleepover | Wonderful 1BD/1BA -Downtown Des Moines
Downtown Des Moines
8.8 out of 10, Excellent, (9 reviews)
"The furniture is very comfortable. The check in and check out is very easy. Also a huge plus is that there a free lot to park in behind the building. Overall a great place to stay . We have stayed there a few times now. "
Canada
Gord J.
The price is €191
includes taxes & fees
11 Feb - 12 Feb
Sleepover | Wonderful 1BD/1BA -Downtown Des Moines

West Des Moines- Garage, Gym, Pool, Jordan Creek

West Des Moines- Garage, Gym, Pool, Jordan Creek
West Des Moines
9.6 out of 10, Exceptional, (11 reviews)
"Great shopping options and very close to the apartment complex."
United States
Jennifer S.
West Des Moines- Garage, Gym, Pool, Jordan Creek

Comfortable stay in historic Sherman Hill-3

Comfortable stay in historic Sherman Hill-3
Downtown Des Moines
8.2 out of 10, Very good, (20 reviews)
"Was exactly what we needed for the long wrestling weekend. Was so nice to go and have a plaiof our own to recover without the chaos of a hotel. Excellent communication and easy checking in and out. "
United States
Joseph
The price is €111
includes taxes & fees
8 Feb - 9 Feb
Comfortable stay in historic Sherman Hill-3

• Lively Cottage 2 King Beds 4 Bed 2 Bath •

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Indianola
9.4 out of 10, Exceptional, (18 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is €203
includes taxes & fees
7 Feb - 8 Feb
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

Sleepover | Prime 1BD/1BA - Downtown Des Moines

Sleepover | Prime 1BD/1BA - Downtown Des Moines
Woodland Heights
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.
Sleepover | Prime 1BD/1BA - Downtown Des Moines

The Hen House Country Living with Farm Life Appeal Indianola, IA

The Hen House Country Living with Farm Life Appeal Indianola, IA
Indianola
10.0 out of 10, Exceptional, (10 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 Hen House Country Living with Farm Life Appeal Indianola, IA

Fun & Charming 1BR Apt near Drake

Fun & Charming 1BR Apt near Drake
Drake
8.0 out of 10, Very good, (2 reviews)
"Abner is amazing. Communication was as smooth as can be, the place was left in great condition, and the house rules were respected. I hope to host them again in the future!"
United States
AbnerG
The price is €854
includes taxes & fees
8 Mar - 9 Mar
Fun & Charming 1BR Apt near Drake

Sleepover | Private 1BD/1BA - Downtown Des Moines

Sleepover | Private 1BD/1BA - Downtown Des Moines
Woodland Heights
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 €180
includes taxes & fees
8 Feb - 9 Feb
Sleepover | Private 1BD/1BA - Downtown Des Moines

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

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Woodland Heights
10.0 out of 10, Exceptional, (69 reviews)
"Great location! Communication with the host was excellent. "
United States
Jamie H.
The price is €275
includes taxes & fees
8 Feb - 9 Feb
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
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

Find out more about Winterset

Everything you need to know about Winterset holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winterset holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winterset holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterset. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterset holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterset holiday rentals we have selected for you start as low as €164 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winterset rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winterset holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterset. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: This holiday home rental outside of Winterset offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind.

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.