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Winterset Vacation Rentals

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Vacation Rentals in Winterset

Terrace/patio
PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!
9.8 out of 10, Exceptional, (32)
"The property itself was very clean and beautiful. We enjoyed our time and stay. The party barn and playset outside the kids really enjoyed. Us adults spent a lot of time in the hot tub. We are planning on renting another property of steven's at the end of the month. Overall experience was 5 stars in our eyes"
The price is $299
$791 total
includes taxes & fees
May 28 - May 29
PARTY BARN 4 GROUPS… PL TBl, PNG PNG, ARCADE, HOT TUB, PATIOS. ACCESS TO POOLS!
Smart TV, video games, table tennis
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!
9.8 out of 10, Exceptional, (27)
"I was in love with this stay! It had plenty of space for us to play board games, hang out, and be together! I would book it again :)"
The price is $199
$506 total
includes taxes & fees
May 23 - May 24
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!
Fridge, microwave, oven, stovetop
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
9.6 out of 10, Exceptional, (27)
"The property had a great basement for hanging out altogether. Hot tub was a nice touch. Plenty of beds for everybody."
The price is $199
$570 total
includes taxes & fees
May 23 - May 24
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
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Interior
SO MICH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
9.4 out of 10, Exceptional, (25)
"Wonderful house with plenty of space and activities for our competitive friend group! We 100% recommend and will book again in the future!"
The price is $249
$637 total
includes taxes & fees
May 23 - May 24
SO MICH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Golf
Quiet Studio on Grand - Downtown DSM!
8.8 out of 10, Excellent, (3)
"Nice cute little studio close to downtown Des Moines. Good communication from the host and easy check in and out."
The price is $72
$170 total
includes taxes & fees
May 23 - May 24
Quiet Studio on Grand - Downtown DSM!
Exterior
Beautiful Rustic Barn just waiting for you to kick back and relax.
10.0 out of 10, Exceptional, (378)
"Convenient"
The price is $115
$191 total
includes taxes & fees
May 23 - May 24
Beautiful Rustic Barn just waiting for you to kick back and relax.
Fridge, microwave, oven, stovetop
Good Vibes 2 Bed Home Centrally Located on Quiet St.
9.8 out of 10, Exceptional, (22)
"Very comfortable & nicely decorated. Like the ceiling fans & night lights. Plenty of pillows & blankets. The hosts are very informative & kind."
Good Vibes 2 Bed Home Centrally Located on Quiet St.
Bathtub, hair dryer, towels, soap
Comfortable and Spacious 3 Bedroom Home
9.6 out of 10, Exceptional, (21)
"Perfect place to stay while celebrating an out of town graduation! Exactly as described."
Comfortable and Spacious 3 Bedroom Home
Outdoor dining
Spacious updated home minutes from Airport and DT!
7.8 out of 10, Good, (7)
"We were in Des Moines for state wrestling and it was nice to come back to a comfortable, quiet spot to regroup. Lots of space and the host was quick to answer any questions."
The price is $135
$329 total
includes taxes & fees
May 27 - May 28
Spacious updated home minutes from Airport and DT!
Fridge, microwave, oven, stovetop
Lovely 2-bedroom apartment in Sherman Hill-4
10.0 out of 10, Exceptional, (3)
"Simply put great stay"
The price is $97
$176 total
includes taxes & fees
May 26 - May 27
Lovely 2-bedroom apartment in Sherman Hill-4
Fridge, microwave, oven, stovetop
6212 Boston Avenue · 3 bdr / 1 bath Fully Remodeled House off Merle Hay
9.8 out of 10, Exceptional, (19)
"Clean property, well maintained and accurately portrayed on the website. Highly recommend for couples or family."
6212 Boston Avenue · 3 bdr / 1 bath Fully Remodeled House off Merle Hay
Free WiFi, bed sheets
Studio Sleeps 4 - Next to 3 Breweries!
10.0 out of 10, Exceptional, (1)
"Nice little appointment, we were just there to sleep really quite at night seemed like a nice neighborhood."
The price is $72
$170 total
includes taxes & fees
May 23 - May 24
Studio Sleeps 4 - Next to 3 Breweries!
Fridge, microwave, oven, stovetop
1519 46th Street · Cute 2-bedroom / 1 bath house completely remodeled
9.4 out of 10, Exceptional, (24)
"The cleanest rental I have ever stayed in. Neighborhood was very quiet. Linens and towels were soft and plush. Kitchen has all the cookware and utensils you need. Furniture was clean. All new appliances in kitchen. Only drawback was small bathroom that is off the kitchen, but ceilings in bathroom were tall so seems bigger. And shower insert was nice for such a small area."
The price is $54
$208 total
includes taxes & fees
May 26 - May 27
1519 46th Street · Cute 2-bedroom / 1 bath house completely remodeled
Property grounds
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
10.0 out of 10, Exceptional, (38)
"Visiting Iowa State - great location for the home - close to downtown and the interstate. Great home away from home!"
The price is $153
$382 total
includes taxes & fees
Jun 12 - Jun 13
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Fridge, microwave, oven, stovetop
Perfect Big Groups~Downtown~Fun Backyard~Pet Frdly
6.4 out of 10, (6)
"Let me start by saying that the property manager Tobias was a good communicator. We had our family Christmas reunion here. The 3 units worked out well for our out of town families to stay. This is an old place that still needs repairs here & there but what house over 100 years old doesn’t. I’m sure it was grand in its early days. I’m happy that the owners have plans for repairs & more updating because I hate to see old homes get run down. There was a leak under one of the kitchen sinks. The...
Perfect Big Groups~Downtown~Fun Backyard~Pet Frdly
Property grounds
Gorgeous Home With Sauna Sleeps 7
9.6 out of 10, Exceptional, (28)
"Nice cozy place where famkly could all be together."
Gorgeous Home With Sauna Sleeps 7
Private kitchen
Home in Clive, GREAT location, cozy, spacious, 5BR w/hot tub!
10.0 out of 10, Exceptional, (7)
"This property is the perfect place to stay for large families or groups. We stayed here while in town on a golf trip with 8 friends. The number of bedrooms, bathrooms, and pristine hot tub were perfect! Nice newer fridge and kitchen/bar area, newer big TV, good WiFi, etc. Many nice updates to the home. A few areas are original/older, but still tasteful. Tessa was awesome to deal with, and the house was so clean!! Can’t recommend it enough."
The price is $563
$968 total
includes taxes & fees
May 26 - May 27
Home in Clive, GREAT location, cozy, spacious, 5BR w/hot tub!
Fridge, microwave, oven, stovetop
Charming 4BR/2BA in central DSM
10.0 out of 10, Exceptional, (13)
"This house truly is charming. There is so much space yet they’ve made it feel so cozy and comforting. Every room is large, beautifully decorated, and clean. My family was only there for a quick night and we were sad we couldn’t stay longer! The neighborhood is quiet and safe -just what we needed for a place to rest our heads while road tripping."
The price is $137
$283 total
includes taxes & fees
Jun 5 - Jun 6
Charming 4BR/2BA in central DSM
Exterior
Charming 4 Bedroom Home With Beautiful Backyard
9.4 out of 10, Exceptional, (45)
"Amazing place close to all we needed in Des Moines! Great hosts !"
Charming 4 Bedroom Home With Beautiful Backyard
Interior
Grand Home on Grand! Spacious Historic Home
9.6 out of 10, Exceptional, (10)
"A group of friends came up for the DM Women's Run. We had plenty of room to sleep and really enjoyed sitting around in the evening."
The price is $250
$478 total
includes taxes & fees
May 28 - May 29
Grand Home on Grand! Spacious Historic Home
Don't see what you're looking for?
See all available properties in Winterset
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.

Winterset Vacation Rental Travel Info

Popular accommodation
Winterset private vacation homes
Known landmarks
Pammel State Park, The Winterset Stage and Roseman Bridge
International airport
Des Moines, IA (DSM-Des Moines Intl.)

Other types of properties in Winterset you may be interested in

Property entrance
Covered Bridge Inn
2.5 star property
9.4 out of 10, Exceptional, (571)
"Very clean and comfortable stay."
The price is $79
$87 total
includes taxes & fees
May 26 - May 27
Covered Bridge Inn
Lobby
Cobblestone Inn & Suites - Winterset, IA
2.5 star property
9.2 out of 10, Wonderful, (531)
"Nice accommodations and good breakfast. "
The price is $102
$114 total
includes taxes & fees
Jun 18 - Jun 19
Cobblestone Inn & Suites - Winterset, IA
Indoor spa tub
Stoney Creek Hotel Des Moines - Johnston
2.5 star property
8.8 out of 10, Excellent, (1167)
"Nice room, friendly staff."
The price is $99
$111 total
includes taxes & fees
May 27 - May 28
Stoney Creek Hotel Des Moines - Johnston
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.

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 $54 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.

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?

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HV IT ALL!: Visitors like this Winterset vacation home rental. It offers a patio, a selection of games, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a spa tub.

How many vacation rentals are there in Winterset?

With 3 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, Roseman Bridge and Madison County Courthouse 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.

Recent reviews of Winterset properties
Expedia verified reviews

AmericInn by Wyndham Des Moines Airport

AmericInn by Wyndham Des Moines Airport

5/5 Excellent
"Very nice staff and clean room"
A verified traveler from Sac City stayed at AmericInn by Wyndham Des Moines Airport
Posted 10 hours ago
AmericInn by Wyndham Des Moines Airport