Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

Winterset Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Winterset

Fridge, microwave, oven, stovetop
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
9.4 out of 10, Exceptional, (57)
"Excellent location and clean property. Plenty of things to do in the area as well as comfortable living space at the property."
United States
Jackie C.
$541 nightly
The price is $606
Nov 3 - Nov 4
Total with taxes and fees
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Fridge, microwave, oven, stovetop
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
9.8 out of 10, Exceptional, (67)
"This was great for our extended family to stay. Plenty of room for everyone. "
United States
Stephanie B.
$490 nightly
The price is $549
Nov 2 - Nov 3
Total with taxes and fees
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Property grounds
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
2.0 star property
8.4 out of 10, Very Good, (30)
"This was such a great place for my friends and me to stay. We needed a nice comfortable place where we could spend an evening catching up and enjoying each other's company and this house was perfect for that. Everything was nice and clean and the hosts have gone above and beyond with the amenities they provided. We would definitely stay here again! "
United States
Pamela A.
$255 nightly
The price is $286
Oct 27 - Oct 28
Total with taxes and fees
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
Fridge, microwave, oven, stovetop
Gem in West Dsm | 4BD/3BA Home | Perfect Location
Gem in West Dsm | 4BD/3BA Home | Perfect Location
9.4 out of 10, Exceptional, (35)
"We didn't spend much time at the house. We were working near by and just needed a place to eat, shower and sleep. We liked the place and would recommend it to others!"
United States
Tiffany L.
Gem in West Dsm | 4BD/3BA Home | Perfect Location
Fridge, microwave, oven, stovetop
Charming Beaverdale 4BR/2BA in central DSM - Safe & Cozy
Charming Beaverdale 4BR/2BA in central DSM - Safe & Cozy
9.4 out of 10, Exceptional, (26)
"This location had the space, comfort and amenities to make our stay enjoyable. "
United States
Mark and Karen S.
Charming Beaverdale 4BR/2BA in central DSM - Safe & Cozy
Terrace/patio
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
10.0 out of 10, Exceptional, (63)
"This house was perfect for our little girl's weekend getaway! The hot tub was so nice to relax in."
United States
Brittany B.
$292 nightly
The price is $327
Nov 17 - Nov 18
Total with taxes and fees
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Terrace/patio
URBAN RETREAT - 4 BEDROOM HOUSE, FAMILY FRIENDLY with ARCADE, GAMES..
URBAN RETREAT - 4 BEDROOM HOUSE, FAMILY FRIENDLY with ARCADE, GAMES..
2.0 star property
10.0 out of 10, Exceptional, (22)
"Very nice and clean house, was perfect for what we needed!"
United States
Jandy P.
URBAN RETREAT - 4 BEDROOM HOUSE, FAMILY FRIENDLY with ARCADE, GAMES..
Fridge, microwave, oven, stovetop
2-bedroom vacation home just 3 minutes drive to Drake University
2-bedroom vacation home just 3 minutes drive to Drake University
9.8 out of 10, Exceptional, (46)
"This house was very clean and family friendly. Very easy to locate. I and my family stay over for 3 days . We travel from cleveland to iowa. "
United States
Princess o.
2-bedroom vacation home just 3 minutes drive to Drake University
Fridge, microwave, oven, stovetop
Lovely 2-bedroom apartment in Sherman Hill-4
Lovely 2-bedroom apartment in Sherman Hill-4
8.4 out of 10, Very Good, (17)
"This was a great location it was about a mile walk to downtown. Very accommodating and excellent communication with host! "
United States
Gretchen R.
$139 nightly
The price is $157
Oct 23 - Oct 24
Total with taxes and fees
Lovely 2-bedroom apartment in Sherman Hill-4
Exterior detail
Waterbury Treasure!
Waterbury Treasure!
10.0 out of 10, Exceptional, (11)
"Great home we booked during our time in Iowa for hinterland. It was a great place to escape to after the music festival!"
United States
Cristian M.
Waterbury Treasure!
Interior
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
10.0 out of 10, Exceptional, (53)
"We had 2 families of young adults and teens. Plenty of space for our needs and well located. "
United States
Jessica O.
$743 nightly
The price is $832
Oct 23 - Oct 24
Total with taxes and fees
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
Private kitchen
Forest Ave Historic Rutledge home 8 beds close to everything in the metro.
Forest Ave Historic Rutledge home 8 beds close to everything in the metro.
9.6 out of 10, Exceptional, (5)
"Very clean and nice place - lots of room and very cozy. Fit all 6 people just fine and was in a good location for things to do. "
United States
Sydney O.
$343 nightly
The price is $384
Oct 28 - Oct 29
Total with taxes and fees
Forest Ave Historic Rutledge home 8 beds close to everything in the metro.
Interior
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
9.8 out of 10, Exceptional, (64)
"Absolutely wonderful property! We are looking into booking again for next year, there was something for everyone to do! Thank you for sharing this little piece of paradise!"
United States
June J.
$656 nightly
The price is $735
Nov 3 - Nov 4
Total with taxes and fees
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
Fridge, microwave, oven, stovetop
Comfortable stay downtown near sculpture park-7
Comfortable stay downtown near sculpture park-7
8.6 out of 10, Excellent, (7)
"We enjoyed our short visit to Des Moines. The space fit our needs nicely. It is an old building with creaky floors, but furnishings are updated. We were close to what we need to do with lots of stores and restaurants near by. "
United States
Kimberly S.
$160 nightly
The price is $181
Oct 26 - Oct 27
Total with taxes and fees
Comfortable stay downtown near sculpture park-7
Microwave, oven, stovetop, dishwasher
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood
9.6 out of 10, Exceptional, (10)
"We stayed for a week and had such a wonderful time. The home is beautiful, clean, comfortable, and the photos are a perfect description. While we were there we saw fireflies, an owl, bunnies, a doe and fawn, chipmunks, squirrels, cardnials, and many others birds. The neighborhood is quiet and beautiful. We absolutely would stay here again."
United States
Karylana J.
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood
Terrace/patio
Luxury condo. 2 car garage, rooftop patio. Perfect for work or play!
Luxury condo. 2 car garage, rooftop patio. Perfect for work or play!
10.0 out of 10, Exceptional, (36)
"We loved this place! Fun location"
United States
Diana H.
Luxury condo. 2 car garage, rooftop patio. Perfect for work or play!
Fridge, microwave, oven, stovetop
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
9.4 out of 10, Exceptional, (71)
"We had a fun time staying at this house. We visited downtown Des Moines and had a great time at Adventureland. The only suggestion would be to have some dish towels in the kitchen. The arcade games, ping pong table and skee-ball were popular with the kids. "
United States
Tracey G.
$432 nightly
The price is $484
Oct 26 - Oct 27
Total with taxes and fees
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Game room
Beautiful home minutes from downtown!
Beautiful home minutes from downtown!
9.4 out of 10, Exceptional, (23)
"Overall we had a nice time and would come back. It was convenient for visiting family without being in each other’s way."
United States
Stephanie M.
$245 nightly
The price is $274
Oct 23 - Oct 24
Total with taxes and fees
Beautiful home minutes from downtown!
Fridge, microwave, oven, stovetop
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom
9.6 out of 10, Exceptional, (24)
"House is mostly updated and huge! We had a good stay. "
United States
Daniel C.
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom
Exterior
Charming 4 Bedroom Home With Beautiful Backyard
Charming 4 Bedroom Home With Beautiful Backyard
9.4 out of 10, Exceptional, (70)
"Great location, great house. "
United States
Christopher H.
Charming 4 Bedroom Home With Beautiful Backyard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winterset Hotel Reviews

AmericInn by Wyndham Des Moines Airport

AmericInn by Wyndham Des Moines Airport

10/10 Excellent
"ok"
Zenaido 3-night trip
Posted 23 hours ago
AmericInn by Wyndham 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 $157 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, Cedar Bridge 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.