Winterset Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Winterset vacation rentals

Microwave, oven, stovetop, dishwasher
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Vacation Home in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
10.0 out of 10, Exceptional, (5)
"We had everything we could possibly need for our stay, a well equipped kitchen, great gathering areas, comfy beds, games, and being centrally located to the things we wanted to see. Our home was nicely decorated and spotlessly clean"
United States
Debbie M.
$314 nightly
The price is $351
Jan 13 - Jan 14
Total with taxes and fees
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Microwave, oven, stovetop, dishwasher
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

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)
"Great location with a cozy, clean, pet-friendly cottage. Had everything we needed. Will stay here again."
United States
Jeff C.
$201 nightly
The price is $225
Jan 4 - Jan 5
Total with taxes and fees
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Fridge, microwave, oven, stovetop
Sleepover: Attractive Studio and Gym - Des Moines

Apartment in Drake

Sleepover: Attractive Studio and Gym - Des Moines
10.0 out of 10, Exceptional, (2)
"Clean and quiet for our stay. "
United States
Jackie
$158 nightly
The price is $177
Jan 4 - Jan 5
Total with taxes and fees
Sleepover: Attractive Studio and Gym - Des Moines
Interior
Quiet Studio on Grand Ave - Heart of Downtown

Apartment in Downtown Des Moines

Quiet Studio on Grand Ave - Heart of Downtown
9.4 out of 10, Exceptional, (6)
"Property was in a good location, street parking was very easy. Host was incredibly responsive and helpful. "
United States
Cameron W.
$931 nightly
The price is $950
Jan 4 - Jan 5
Total with taxes and fees
Quiet Studio on Grand Ave - Heart of Downtown
Smart TV, fireplace
Sleepover: Charming 1BD/1BA - Downtown Des Moines

Apartment in Woodland Heights

Sleepover: Charming 1BD/1BA - Downtown Des Moines
10.0 out of 10, Exceptional, (1)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
$167 nightly
The price is $187
Jan 4 - Jan 5
Total with taxes and fees
Sleepover: Charming 1BD/1BA - Downtown Des Moines
Interior
Sleepover: Impressive Studio and Gym - Des Moines

Apartment in Drake

Sleepover: Impressive Studio and Gym - Des Moines
10.0 out of 10, Exceptional, (2)
"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
$158 nightly
The price is $177
Jan 4 - Jan 5
Total with taxes and fees
Sleepover: Impressive Studio and Gym - Des Moines
Interior
Fun & Charming 1BR Apt near Drake

Apartment in Drake

Fun & Charming 1BR Apt near Drake
8.0 out of 10, Very Good, (2)
"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 4 - Jan 5
Total with taxes and fees
Fun & Charming 1BR Apt near Drake
Fridge, oven, stovetop, coffee/tea maker
Beautiful 2BR N of Grand near Downtown

Vacation Home in North of Grand

Beautiful 2BR N of Grand near Downtown
8.0 out of 10, Very Good, (2)
"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.
$975 nightly
The price is $998
Jan 4 - Jan 5
Total with taxes and fees
Beautiful 2BR N of Grand near Downtown
Outdoor dining
Family & Pet-Friendly 2BR Retreat Near Downtown

Vacation Home in Greater South Side

Family & Pet-Friendly 2BR Retreat Near Downtown
10.0 out of 10, Exceptional, (12)
"Great location and had everything we needed! "
United States
Cooper R.
$216 nightly
The price is $242
Jan 4 - Jan 5
Total with taxes and fees
Family & Pet-Friendly 2BR Retreat Near Downtown
Fridge, microwave, oven, stovetop
Historic Valley Junction Loft

Apartment in West Des Moines

Historic Valley Junction Loft
9.8 out of 10, Exceptional, (21)
"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 9 - Jan 10
Total with taxes and fees
Historic Valley Junction Loft
Fridge, microwave, oven, stovetop
Lovely 2-bedroom apartment in Sherman Hill-4

Apartment in Downtown Des Moines

Lovely 2-bedroom apartment in Sherman Hill-4
8.4 out of 10, Very Good, (18)
"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 4 - Jan 5
Total with taxes and fees
Lovely 2-bedroom apartment in Sherman Hill-4
Fridge, microwave, oven, stovetop
The Hen House Country Living with Farm Life Appeal Indianola, IA

Vacation Home in Indianola

The Hen House Country Living with Farm Life Appeal Indianola, IA
10.0 out of 10, Exceptional, (8)
"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
Jan 4 - Jan 5
Total with taxes and fees
The Hen House Country Living with Farm Life Appeal Indianola, IA
Fridge, microwave, oven, stovetop
The Cozy Cottage - Entire house in Des Moines

Vacation Home in Greater South Side

The Cozy Cottage - Entire house in Des Moines
9.6 out of 10, Exceptional, (7)
"This place worked for us 3 adults well. The beds were comfy and a quiet neighborhood. Wed stay there again. "
United States
Shelley B.
$187 nightly
The price is $200
Jan 4 - Jan 5
Total with taxes and fees
The Cozy Cottage - Entire house in Des Moines
Fridge, microwave, oven, stovetop
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

Vacation Home in Indianola

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
9.4 out of 10, Exceptional, (18)
"Had a great stay, will come back!"
United States
Spring A.
$215 nightly
The price is $241
Jan 5 - Jan 6
Total with taxes and fees
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Terrace/patio
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

Vacation Home in Woodland Heights

The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
10.0 out of 10, Exceptional, (67)
"Wonderful, Close to everything we wanted to do. Very clean and had comfy bed "
United States
M&S D.
$292 nightly
The price is $327
Jan 13 - Jan 14
Total with taxes and fees
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
Terrace/patio
Farmhouse Oasis

Vacation Home in Dallas Center

Farmhouse Oasis
10.0 out of 10, Exceptional, (19)
"A wonderfully peaceful farm setting with a great private fenced yard for us and our dog. "
United States
Jennifer B.
$148 nightly
The price is $156
Jan 5 - Jan 6
Total with taxes and fees
Farmhouse Oasis
Fridge, microwave, oven, stovetop
Newly Remodeled Brick Home with wall Sculptures by the Airport

Vacation Home in Southwestern Hills

Newly Remodeled Brick Home with wall Sculptures by the Airport
10.0 out of 10, Exceptional, (51)
"Great place"
United States
Rebecca E.
$205 nightly
The price is $230
Jan 26 - Jan 27
Total with taxes and fees
Newly Remodeled Brick Home with wall Sculptures by the Airport
Terrace/patio
Downtown Skyline Views in Modern Townhome with Rooftop Patios

Vacation Home in Downtown Des Moines

Downtown Skyline Views in Modern Townhome with Rooftop Patios
10.0 out of 10, Exceptional, (43)
"A great place to stay if visiting Des Moines!"
United States
Justine
$220 nightly
The price is $246
Feb 1 - Feb 2
Total with taxes and fees
Downtown Skyline Views in Modern Townhome with Rooftop Patios
Fridge, microwave, oven, stovetop
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts

Apartment in Waukee

Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
2.0 star property
10.0 out of 10, Exceptional, (8)
"The location was was close top everything that we needed. We were very impressed with the cleanliness of the condo!"
United States
Bill S.
$216 nightly
The price is $241
Jan 3 - Jan 4
Total with taxes and fees
Good Vibes 2-Bedroom Apartment in Waukee - Central Location & Modern Comforts
Property grounds
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Vacation Home in Greater South Side

Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
2.0 star property
8.4 out of 10, Very Good, (35)
"Nice place for the family! "
United States
Brandon G.
$287 nightly
The price is $321
Jan 4 - Jan 5
Total with taxes and fees
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
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

Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

10/10 Excellent
"Super friendly and helpful staff. Room was clean and very affordable. Perfect Park and Fly after several canceled flights due to the weather. 5 minute shuttle to the airport."
Milton 1-night trip
Posted 2 days ago
Days Inn & Suites 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 $177 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?

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, Clark Tower and Cedar 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.