Winterset Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Winterset vacation rentals

Outdoor dining

Vacation 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.
$296 nightly
The price is $331
Jan 26 - Jan 27
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Smart TV, fireplace

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.
$164 nightly
The price is $186
Jan 23 - Jan 24
Total with taxes and fees
Sleepover | Charming 1BD/1BA - Downtown Des Moines
2 bedrooms, iron/ironing board, WiFi, bed sheets

Cottage in Woodland Heights

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
2.0 star property
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.
$186 nightly
The price is $208
Jan 21 - Jan 22
Total with taxes and fees
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Free WiFi, bed sheets

Apartment in Downtown Des Moines

Quiet Studio on Grand Ave - Heart of Downtown
9.4 out of 10, Exceptional, (6 reviews)
"Property was in a good location, street parking was very easy. Host was incredibly responsive and helpful. "
United States
Cameron W.
$928 nightly
The price is $947
Jan 21 - Jan 22
Total with taxes and fees
Quiet Studio on Grand Ave - Heart of Downtown
Smart TV

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
$154 nightly
The price is $188
Jan 21 - Jan 22
Total with taxes and fees
Sleepover | Attractive Studio and Gym - Des Moines
Smart TV

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
$154 nightly
The price is $175
Jan 21 - Jan 22
Total with taxes and fees
Sleepover | Impressive Studio and Gym - Des Moines
Interior

Apartment in Drake

Fun & Charming 1BR Apt near 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
$968 nightly
The price is $989
Jan 21 - Jan 22
Total with taxes and fees
Fun & Charming 1BR Apt near Drake
Exterior

Cabin in Osceola

Cozy pond house nestled in nature waiting for you to enjoy
2.0 star property
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.
$160 nightly
The price is $168
Jan 21 - Jan 22
Total with taxes and fees
Cozy pond house nestled in nature waiting for you to enjoy
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.
$1,541 nightly
The price is $1,571
Jan 21 - Jan 22
Total with taxes and fees
2BR 2 BA Apt Downtown w/Hot Tub & Amenities!
Smart TV, fireplace

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.
$164 nightly
The price is $186
Jan 21 - Jan 22
Total with taxes and fees
Sleepover | Private 1BD/1BA - Downtown Des Moines
Smart TV, fireplace

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.
$174 nightly
The price is $197
Feb 1 - Feb 2
Total with taxes and fees
Sleepover | Prime 1BD/1BA - Downtown Des Moines
Smart TV

Vacation 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.
$214 nightly
The price is $240
Jan 21 - Jan 22
Total with taxes and fees
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Smart TV

Apartment in Downtown Des Moines

Lovely 2-bedroom apartment in Sherman Hill-4
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.
$113 nightly
The price is $128
Jan 25 - Jan 26
Total with taxes and fees
Lovely 2-bedroom apartment in Sherman Hill-4
Dining

Apartment in Downtown Des Moines

Comfortable stay in historic Sherman Hill-3
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
$113 nightly
The price is $128
Jan 27 - Jan 28
Total with taxes and fees
Comfortable stay in historic Sherman Hill-3
Smart TV, printers

Apartment in Waukee

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
2.0 star property
10.0 out of 10, Exceptional, (9 reviews)
"The location was was close top everything that we needed. We were very impressed with the cleanliness of the condo!"
United States
Bill S.
$223 nightly
The price is $249
Jan 23 - Jan 24
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Smart TV

Vacation Home in North of Grand

Beautiful 2BR N of Grand near Downtown
8.0 out of 10, Very Good, (2 reviews)
"Great place, clean, organized, well maintained and the hosts have made it a comfortable cozy welcoming space. So well stocked with everything you need to make it easy to be away from home. Great location."
United States
Michael B.
$969 nightly
The price is $992
Jan 21 - Jan 22
Total with taxes and fees
Beautiful 2BR N of Grand near Downtown
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.
$124 nightly
The price is $139
Jan 21 - Jan 22
Total with taxes and fees
Historic Valley Junction Loft
Microwave, oven, stovetop

Apartment in Downtown Des Moines

Experience Sherman Hill from the Olive 3, 1 bed apartment in downtown Des Moines
2.0 star property
$152 nightly
The price is $170
Feb 2 - Feb 3
Total with taxes and fees
Experience Sherman Hill from the Olive 3, 1 bed apartment in downtown Des Moines
Smart TV

Apartment in West Des Moines

Sleepover | Alluring 1BD/1BA - Des Moines
$154 nightly
The price is $175
Jan 21 - Jan 22
Total with taxes and fees
Sleepover | Alluring 1BD/1BA - Des Moines
Property grounds

Vacation 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
$148 nightly
The price is $156
Jan 21 - Jan 22
Total with taxes and fees
Farmhouse Oasis
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

Quality Inn & Suites Des Moines Airport

Quality Inn & Suites Des Moines Airport

10/10 Excellent
"Clean room, smell clean when you walk in , staff very polite. Clean rooms, housekeepers daily."
Jessica 4-night trip
Posted 19 hours ago
Quality Inn & Suites Des Moines Airport

Find out more about Winterset

Everything you need to know about Winterset vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winterset vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winterset in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winterset?

Yes, you can find vacation rentals close to well known local attractions in Winterset, or you can choose a secluded option if you're looking for relaxation. 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 vacation rentals in Winterset?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: Visitors like this Winterset vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winterset?

With 5 Expedia vacation rentals, you're sure 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 vacation rentals like in Winterset?

Vacation rentals are private properties you can stay in for several days or longer in Winterset. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.