Winterset Vacation Rentals

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Our top choices for Winterset vacation 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.
$284 nightly
The price is $318
Feb 23 - Feb 24
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Beautiful Rustic Barn just waiting for you to kick back and relax.

Beautiful Rustic Barn just waiting for you to kick back and relax.
NEW VIRGINIA
10.0 out of 10, Exceptional, (406 reviews)
"Amazing property "
United States
Anonymous traveler
$174 nightly
The price is $183
Feb 20 - Feb 21
Total with taxes and fees
Beautiful Rustic Barn just waiting for you to kick back and relax.

Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Serenity Heights - Peaceful Country Acres with beautiful view in every direction
Osceola
10.0 out of 10, Exceptional, (84 reviews)
"Host was very accommodating and was very quick to respond to texts. The house and the views were amazing!"
United States
AARON D.
$294 nightly
The price is $308
Feb 22 - Feb 23
Total with taxes and fees
Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Farmhouse Oasis

Farmhouse Oasis
Dallas Center
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
$151 nightly
The price is $159
Feb 23 - Feb 24
Total with taxes and fees
Farmhouse Oasis

Historic Valley Junction Loft

Historic Valley Junction Loft
West Des Moines
9.8 out of 10, Exceptional, (22 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
Feb 25 - Feb 26
Total with taxes and fees
Historic Valley Junction Loft

Downtown Skyline Views in Modern Townhome with Rooftop Patios

Downtown Skyline Views in Modern Townhome with Rooftop Patios
Downtown Des Moines
10.0 out of 10, Exceptional, (48 reviews)
"A great place to stay if visiting Des Moines!"
United States
Justine
$266 nightly
The price is $298
Feb 22 - Feb 23
Total with taxes and fees
Downtown Skyline Views in Modern Townhome with Rooftop Patios

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!
Waukee
9.8 out of 10, Exceptional, (75 reviews)
"Perfect location, plenty of space for our group."
United States
Joan J.
$439 nightly
The price is $492
Feb 23 - Feb 24
Total with taxes and fees
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

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!
West Des Moines
9.8 out of 10, Exceptional, (73 reviews)
"Excellent location to stay for larger family staying several days for a wedding. Very close to shopping and restaurants. "
United States
Tracey S.
$647 nightly
The price is $725
Feb 23 - Feb 24
Total with taxes and fees
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

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
$180 nightly
The price is $189
Feb 22 - Feb 23
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA

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!!
Woodland Heights
9.4 out of 10, Exceptional, (70 reviews)
"Great place to stay with family/friends "
United States
Eric V.
$438 nightly
The price is $491
Feb 22 - Feb 23
Total with taxes and fees
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

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, (70 reviews)
"Great location! Communication with the host was excellent. "
United States
Jamie H.
$292 nightly
The price is $327
Feb 25 - Feb 26
Total with taxes and fees
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

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!
Urbandale
9.4 out of 10, Exceptional, (76 reviews)
"Loved the stay just wish the pool was on site, overall no complaints "
United States
Arika R.
$381 nightly
The price is $427
Feb 22 - Feb 23
Total with taxes and fees
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!

The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym

The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym
West Des Moines
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stay! So much better than a hotel room!!"
United States
Janell R.
$222 nightly
The price is $249
Mar 17 - Mar 18
Total with taxes and fees
The Cascades at Jordan Creek WDSM/Pool/Tanning/Gym

The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14

The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14
Drake
10.0 out of 10, Exceptional, (22 reviews)
"Check in was a breeze as well as great communication with the owners. We stayed for 3 days and had more than enough extras so we didnt need much for the house. Would definitely stay there again!"
United States
Azeneth B.
$341 nightly
The price is $382
Feb 22 - Feb 23
Total with taxes and fees
The CORN CRIB: Spa - Game Room - BBQ - Office - DOWNTOWN - Sleeps 14

• 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.
$212 nightly
The price is $237
Feb 22 - Feb 23
Total with taxes and fees
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (29 reviews)
"What a great place to stay! "
United States
Annie P.
$245 nightly
The price is $274
Feb 22 - Feb 23
Total with taxes and fees
Beautiful home minutes from downtown!

Spacious Valley Junction Retreat

Spacious Valley Junction Retreat
West Des Moines
9.8 out of 10, Exceptional, (30 reviews)
"The kitchen was amazing. Had everything we needed. The game room was amazing and my whole family enjoyed it. The rooms were nice and comfortable. The neighborhood was quiet and communication was amazing"
United States
Tammy T.
$309 nightly
The price is $346
Mar 16 - Mar 17
Total with taxes and fees
Spacious Valley Junction Retreat

Spacious 4BR Home • WiFi • Family-Friendly • Waukee

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (24 reviews)
"Well equipped and great location"
United States
Josh H.
$275 nightly
The price is $307
Feb 22 - Feb 23
Total with taxes and fees
Spacious 4BR Home • WiFi • Family-Friendly • Waukee

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.
$190 nightly
The price is $192
Feb 25 - Feb 26
Total with taxes and fees
West Des Moines- Garage, Gym, Pool, Jordan Creek

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Waukee
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.
$217 nightly
The price is $242
Feb 22 - Feb 23
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
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 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 $139 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?

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!: Visitors like this Winterset vacation home rental. It is located next to a golf course and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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, Roseman Bridge and Clark Tower 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.