Winterset Vacation Rentals

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Winterset vacation rentals

Outdoor dining
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 reviews)
"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.
The price is ￥16,421
￥51,637 total
includes taxes & fees
Jan 12 - Jan 13
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
2 bedrooms, iron/ironing board, WiFi, bed sheets
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 reviews)
"Great location with a cozy, clean, pet-friendly cottage. Had everything we needed. Will stay here again."
United States
Jeff C.
The price is ￥13,500
￥35,458 total
includes taxes & fees
Jan 12 - Jan 13
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Exterior
Cozy pond house nestled in nature waiting for you to enjoy

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.
The price is ￥16,578
￥26,525 total
includes taxes & fees
Jan 12 - Jan 13
Cozy pond house nestled in nature waiting for you to enjoy
Terrace/patio
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 review)
"Convenient to Sherman Hill and downtown. Quiet. "
United States
Abby H.
The price is ￥11,226
￥31,142 total
includes taxes & fees
Jan 25 - Jan 26
Sleepover: Charming 1BD/1BA - Downtown Des Moines
1 bedroom, free WiFi, bed sheets
Sleepover: Attractive Studio and Gym - Des Moines

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
The price is ￥8,384
￥27,959 total
includes taxes & fees
Jan 14 - Jan 15
Sleepover: Attractive Studio and Gym - Des Moines
Smart TV
• 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 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is ￥15,789
￥37,489 total
includes taxes & fees
Jan 15 - Jan 16
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
1 bedroom, free WiFi, bed sheets
Sleepover: Impressive Studio and Gym - Des Moines

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
The price is ￥8,384
￥27,959 total
includes taxes & fees
Jan 12 - Jan 13
Sleepover: Impressive Studio and Gym - Des Moines
Smart TV
Historic Valley Junction Loft

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.
The price is ￥12,434
￥21,884 total
includes taxes & fees
Jan 23 - Jan 24
Historic Valley Junction Loft
Interior
The Cozy Cottage - Entire house in Des Moines

Vacation Home in Greater South Side

The Cozy Cottage - Entire house in Des Moines
9.4 out of 10, Exceptional, (8 reviews)
"It was perfect for our needs !"
United States
Mandy T.
The Cozy Cottage - Entire house in Des Moines
Free WiFi, bed sheets
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 reviews)
"Property was in a good location, street parking was very easy. Host was incredibly responsive and helpful. "
United States
Cameron W.
The price is ￥6,600
￥149,481 total
includes taxes & fees
Jan 14 - Jan 15
Quiet Studio on Grand Ave - Heart of Downtown
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, (9 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
The price is ￥21,315
￥29,841 total
includes taxes & fees
Jan 13 - Jan 14
The Hen House Country Living with Farm Life Appeal Indianola, IA
Exterior
Beautiful home minutes from downtown!

Vacation Home in Des Moines

Beautiful home minutes from downtown!
9.6 out of 10, Exceptional, (26 reviews)
"What a great place to stay! "
United States
Annie P.
The price is ￥18,473
￥43,325 total
includes taxes & fees
Jan 12 - Jan 13
Beautiful home minutes from downtown!
Smart TV
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 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.
The price is ￥10,768
￥156,611 total
includes taxes & fees
Jan 12 - Jan 13
Beautiful 2BR N of Grand near Downtown
Interior
Fun & Charming 1BR Apt near Drake

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
The price is ￥7,468
￥156,074 total
includes taxes & fees
Jan 14 - Jan 15
Fun & Charming 1BR Apt near Drake
Interior
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!

Vacation Home in Urbandale

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
9.4 out of 10, Exceptional, (74 reviews)
"Excellent property with a ton of amenities! Everything we needed was there and easy to find."
United States
Jacob F.
The price is ￥14,068
￥58,198 total
includes taxes & fees
Jan 12 - Jan 13
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Property grounds
Beautiful Rustic Barn just waiting for you to kick back and relax.

Vacation Home in NEW VIRGINIA

Beautiful Rustic Barn just waiting for you to kick back and relax.
10.0 out of 10, Exceptional, (406 reviews)
"Amazing property "
United States
Anonymous traveler
The price is ￥18,157
￥30,007 total
includes taxes & fees
Jan 12 - Jan 13
Beautiful Rustic Barn just waiting for you to kick back and relax.
TV
Beautiful 3-bedroom house with AC in adorable Des Moines

Vacation Home in Beaverdale

Beautiful 3-bedroom house with AC in adorable Des Moines
2.0 star property
9.0 out of 10, Wonderful, (2 reviews)
"Great location close to friends. Hosts were great with awesome communication. "
United States
Karen G.
The price is ￥15,410
￥38,479 total
includes taxes & fees
Jan 12 - Jan 13
Beautiful 3-bedroom house with AC in adorable Des Moines
Property grounds
Farmhouse Oasis

Vacation Home in Dallas Center

Farmhouse Oasis
10.0 out of 10, Exceptional, (19 reviews)
"Incredibly clean and cozy place! Loved the quiet peaceful location and close proximity to the events I had planned for the trip! Wonderful hosts!"
United States
Lindsey C.
The price is ￥12,347
￥24,569 total
includes taxes & fees
Jan 12 - Jan 13
Farmhouse Oasis
Smart TV
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 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.
The price is ￥8,294
￥20,133 total
includes taxes & fees
Jan 18 - Jan 19
Lovely 2-bedroom apartment in Sherman Hill-4
TV, offices
Comfortable 3-bedroom, 1.5-bathroom duplex apartment with full kitchen, laundry, and off-street parking. Minutes from Drake University and downtown Des Moines.

Apartment in Waterbury

Comfortable 3-bedroom, 1.5-bathroom duplex apartment with full kitchen, laundry, and off-street parking. Minutes from Drake University and downtown Des Moines.
7.8 out of 10, Good, (7 reviews)
"Great place! Worked very well for the 4 of us. Thanks very much. We will stay here again in the future!"
United States
Tom H.
The price is ￥13,721
￥167,650 total
includes taxes & fees
Jan 12 - Jan 13
Comfortable 3-bedroom, 1.5-bathroom duplex apartment with full kitchen, laundry, and off-street parking. Minutes from Drake University and downtown Des Moines.
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

Drury Inn & Suites West Des Moines

Drury Inn & Suites West Des Moines

10/10 Excellent
"Courteous staff. Clean. Comfortable."
Allen 1-night trip
Posted 4 days ago
Drury Inn & Suites West Des Moines

Find out more about Winterset

Search for holiday rentals in Winterset on Expedia! You can easily find your home rentals, villas, holiday apartments in Winterset using one of the methods below:

  • View our selection of featured holiday rentals in Winterset
  • Use the map to find apartments and other holiday homes in the Winterset neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winterset while they last

Look no further and take a look at our great range of rental properties in Winterset!

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 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.