A red covered bridge over a calm river, surrounded by lush greenery and trees.

Holiday Homes in Winterset

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winterset holiday homes

A deck with a table and chairs, surrounded by a wooden deck and a white railing.

1. 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, (15 reviews)
"The house in Winterset was perfect in every way. It was beautifully furnished and extremely comfortable. We are so glad we stayed there."
United States
Nickay M.
The price is AU$494
includes taxes & fees
20 Oct - 21 Oct
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A bar area with a large 'M' logo on the wall, shelves with bottles, and a counter with bar tools.

2. Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
Cumming
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay!"
United States
Elizabeth V.
The price is AU$682
includes taxes & fees
5 Oct - 6 Oct
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A garden with a stream, rocks, and flowers.

3. 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, (414 reviews)
"This place was so incredibly cute. We loved our little getaway for our first anniversary and we had everything we needed and more. Thank you for providing such a great place, we’ll definitely be back!!"
United States
Genevieve P.
The price is AU$302
includes taxes & fees
5 Oct - 6 Oct
Beautiful Rustic Barn just waiting for you to kick back and relax.
A single-story house with a front yard, a mailbox, and a tree.

4. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (30 reviews)
"The property was great and would stay again and recommend to family and friends if ciming into town."
United States
Michael D.
The price is AU$252
includes taxes & fees
5 Oct - 6 Oct
Farmhouse Oasis
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

5. Spacious Farmhouse beautifully decorated waiting for laughs and memories

Spacious Farmhouse beautifully decorated waiting for laughs and memories
New Virginia
10.0 out of 10, Exceptional, (21 reviews)
"Very nice place to stay."
United States
Todd W.
The price is AU$331
includes taxes & fees
6 Oct - 7 Oct
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

6. 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, (18 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is AU$277
includes taxes & fees
5 Oct - 6 Oct
The Hen House Country Living with Farm Life Appeal Indianola, IA
A Staybridge hotel with a brick facade, multiple windows, and a covered entrance.

7. Studio Suite w/ Jetted Tub | Free Breakfast!

Studio Suite w/ Jetted Tub | Free Breakfast!
West Des Moines
The price is AU$249
includes taxes & fees
1 Nov - 2 Nov
Studio Suite w/ Jetted Tub | Free Breakfast!
A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

8. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (11 reviews)
"Nice place"
United States
Dale T.
The price is AU$333
includes taxes & fees
4 Oct - 5 Oct
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A dining room with a wooden table, chairs, a bench, a chandelier, and a potted plant.

9. •Delightful 5b stay in Paradise!!•

•Delightful 5b stay in Paradise!!•
Waukee
9.8 out of 10, Exceptional, (21 reviews)
"It was perfect for our family getaway!"
United States
justine p.
The price is AU$602
includes taxes & fees
25 Oct - 26 Oct
•Delightful 5b stay in Paradise!!•
A bedroom with a bed, curtains, a lamp, and a view of the outdoors.

10. • Iconic Lustron home with 2 king beds •

• Iconic Lustron home with 2 king beds •
Windsor Heights
9.0 out of 10, Wonderful, (6 reviews)
"We had a week packed full of fun visiting several locations in and around Windsor Heights, Iowa. The place was perfect for our sleeping needs. "
United States
Martina G.
The price is AU$302
includes taxes & fees
22 Oct - 23 Oct
• Iconic Lustron home with 2 king beds •
A modern living room with a grey sectional sofa, a small white table, and a large round rug. There are two windows with floral curtains, a wooden door, and a white ceiling.

11. Beautiful 3-bedroom house with AC in adorable Des Moines

Beautiful 3-bedroom house with AC in adorable Des Moines
Beaverdale
9.6 out of 10, Exceptional, (21 reviews)
"Perfect for our needs. The host was very communicative during our stay and check-in and check-out was simple and smooth. Great value and we would stay here again!"
United States
Michael G.
The price is AU$400
includes taxes & fees
7 Oct - 8 Oct
Beautiful 3-bedroom house with AC in adorable Des Moines
A residential neighborhood with a house featuring a stone foundation, a sloped roof, and a front yard with a tree and a small garden.

12. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.4 out of 10, Exceptional, (45 reviews)
"Very clean and spacious. Good location to downtown. Very comfortable home. Would recommend and would stay again!!"
United States
Melissa W.
The price is AU$397
includes taxes & fees
4 Oct - 5 Oct
Beautiful home minutes from downtown!
A modern kitchen with stainless steel appliances, dark cabinetry, and a granite countertop.

13. 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
9.6 out of 10, Exceptional, (98 reviews)
"Such a fabulous property and located perfected by lots of fun things to do."
United States
Landon B.
The price is AU$968
includes taxes & fees
7 Oct - 8 Oct
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
A spacious kitchen with wooden cabinets, a central island, and a sliding glass door leading to an outdoor area with a deck and chairs.

14. Home w/Hot Tub -Spacious, Quiet Neighborhood Near Des Moines, IA.

Home w/Hot Tub -Spacious, Quiet Neighborhood Near Des Moines, IA.
Clive
10.0 out of 10, Exceptional, (25 reviews)
"The house is nicely equipped and very comfortable. We enjoyed our stay! "
United States
Kristin H.
The price is AU$934
includes taxes & fees
2 Nov - 3 Nov
Home w/Hot Tub -Spacious, Quiet Neighborhood Near Des Moines, IA.
A dining area with a wooden table set for four, a brown leather sofa, and a large window with a view of bare trees.

15. Centrally Located Wooded A-Frame

Centrally Located Wooded A-Frame
Southwestern Hills
10.0 out of 10, Exceptional, (16 reviews)
"another great stay very peaceful and quiet will stay here again"
United States
chris s.
The price is AU$535
includes taxes & fees
5 Oct - 6 Oct
Centrally Located Wooded A-Frame
A pathway leading to a gated area with lush green foliage on both sides.

16. 3-bedroom townhome in serene West Des Moines with AC

3-bedroom townhome in serene West Des Moines with AC
West Des Moines
8.0 out of 10, Very good, (2 reviews)
"It was a nice place for a quick girls getaway!"
United States
T D.
The price is AU$406
includes taxes & fees
5 Oct - 6 Oct
3-bedroom townhome in serene West Des Moines with AC
A two-story brick house with a front porch, a small garden, and a clear sky.

17. Walnut Row, Walk to Valley Junction, Sleeps 10+

Walnut Row, Walk to Valley Junction, Sleeps 10+
West Des Moines
10.0 out of 10, Exceptional, (4 reviews)
"I can't say enough about our stay at Walnut place. Very cozy and comfortable. we had more room than we needed. Comfortable beds, close to dining and shopping and most importantly it was CLEAN! If were in the area again, we will certainly stay here again and again!"
United States
Tracie F.
The price is AU$675
includes taxes & fees
4 Oct - 5 Oct
Walnut Row, Walk to Valley Junction, Sleeps 10+
A hot tub with a purple light, surrounded by outdoor furniture and string lights.

18. 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, (76 reviews)
"This was a charming house with space for our group of 6. Very clean throughout with comfortable beds. The location made getting around easy."
United States
Chris M.
The price is AU$460
includes taxes & fees
20 Oct - 21 Oct
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
A spacious living area with a pool table, a fireplace, and a dining area with a bench and table.

19. RARE Mid-Mod Home. Spacious inside-and-out.

RARE Mid-Mod Home. Spacious inside-and-out.
Urbandale
9.8 out of 10, Exceptional, (16 reviews)
"I nice place for a few couples to land with plenty of room and great location. Host is great!"
United States
James D.
The price is AU$817
includes taxes & fees
7 Oct - 8 Oct
RARE Mid-Mod Home. Spacious inside-and-out.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

20. The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown

The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown
Windsor Heights
10.0 out of 10, Exceptional, (32 reviews)
"Perfect spot for our family celebrating a graduation. Host was SO Accommodating."
United States
Tim B.
The price is AU$692
includes taxes & fees
7 Oct - 8 Oct
The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown
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

Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston

10/10 Excellent
"Staff was great, our room was very clean."
LeRoy 1-night trip
Posted less than an hour ago
Stoney Creek Hotel Des Moines - Johnston

Find out more about Winterset

Winterset Holiday Homes information

Number of reviews
851
Accommodation
159 Holiday Homes
Lowest Price
AU$249
Highest Price
AU$968