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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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 £246
includes taxes & fees
2 Nov - 3 Nov
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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 £307
includes taxes & fees
2 Nov - 3 Nov
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...
A residential house with a well-maintained lawn, a stone pathway, and a variety of trees and shrubs.

3. 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
West Des Moines
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful place to stay and very accommodating host."
United States
Amy K.
The price is £123
includes taxes & fees
1 Nov - 2 Nov
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
A garden with a stream, rocks, and flowers.

4. 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, (415 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 £134
includes taxes & fees
28 Oct - 29 Oct
Beautiful Rustic Barn just waiting for you to kick back and relax.
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 £133
includes taxes & fees
28 Oct - 29 Oct
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A single-story house with a front yard, a mailbox, and a tree.

6. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (32 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 £133
includes taxes & fees
28 Oct - 29 Oct
Farmhouse Oasis
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

7. 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, (19 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is £145
includes taxes & fees
9 Nov - 10 Nov
The Hen House Country Living with Farm Life Appeal Indianola, IA
A modern kitchen with dark wooden cabinets, a stainless steel stove, and a granite countertop.

8. Adel 4BR/Game Room, Park Nearby & Sleeps 12

Adel 4BR/Game Room, Park Nearby & Sleeps 12
Adel
8.0 out of 10, Very good, (4 reviews)
"The house itself was beautiful. It was very clean and was decorated really cute. There were three bathrooms to go with the four bedrooms, so everyone had their own private space which was really nice. House was in a nice, quiet neighborhood. Would definitely stay here again if we are in the area."
United States
Darla F.
The price is £281
includes taxes & fees
2 Nov - 3 Nov
Adel 4BR/Game Room, Park Nearby & Sleeps 12
A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

9. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (11 reviews)
"We absolutely loved our stay. The place was clean and comfortable. Very peaceful and quiet."
United States
Ana M.
The price is £170
includes taxes & fees
9 Nov - 10 Nov
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A modern kitchen with a dining area, wooden flooring, and a large window offering a view of the backyard.

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (43 reviews)
"Very nice quiet place to stay. Beds were nice and comfy. Nice kitchen and laundry area.We enjoyed our stay"
United States
Doreen
The price is £314
includes taxes & fees
21 Nov - 22 Nov
Spacious 4BR Home • WiFi • Family-Friendly • Waukee
A dining room with a wooden table, chairs, a bench, a chandelier, and a potted plant.

11. •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 £319
includes taxes & fees
22 Nov - 23 Nov
•Delightful 5b stay in Paradise!!•
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.

12. 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, (23 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 £211
includes taxes & fees
2 Nov - 3 Nov
Beautiful 3-bedroom house with AC in adorable Des Moines
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, (101 reviews)
"Excellent place to stay"
United States
Jenny B.
The price is £514
includes taxes & fees
2 Nov - 3 Nov
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
A modern hotel lobby with seating areas, a bar, and a television mounted on the wall.

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

Studio Suite w/ Jetted Tub | Free Breakfast!
West Des Moines
The price is £118
includes taxes & fees
10 Nov - 11 Nov
Studio Suite w/ Jetted Tub | Free Breakfast!
A spacious living room with hardwood flooring, a fireplace, and a chandelier.

15. 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, (5 reviews)
The price is £332
includes taxes & fees
28 Oct - 29 Oct
Walnut Row, Walk to Valley Junction, Sleeps 10+
A residential neighborhood with a house featuring a stone foundation, a sloped roof, and a front yard with a tree and a small garden.

16. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.2 out of 10, Wonderful, (48 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 £209
includes taxes & fees
9 Nov - 10 Nov
Beautiful home minutes from downtown!
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

17. 3-bedroom townhome in serene West Des Moines with AC

3-bedroom townhome in serene West Des Moines with AC
West Des Moines
8.8 out of 10, Excellent, (3 reviews)
"It was a nice place for a quick girls getaway!"
United States
T D.
The price is £212
includes taxes & fees
29 Oct - 30 Oct
3-bedroom townhome in serene West Des Moines with AC
A dining area with a wooden table and chairs, a fireplace, and a wall with a colorful abstract painting.

18. Electric Velvet- 3 bedroom stay near downtown Des Moines

Electric Velvet- 3 bedroom stay near downtown Des Moines
Des Moines
5.8 out of 10, (6 reviews)
"The colors and fun vibe of this house shown in the pics is so much better in person! Check in was smooth- communication with the host was fantastic. We did have some hiccups with cleanliness and finding amenities listed but once the host was contacted, it was made right! Would stay here again! "
United States
Kristal D.
The price is £212
includes taxes & fees
10 Nov - 11 Nov
Electric Velvet- 3 bedroom stay near downtown Des Moines
A spacious living room with a fireplace, a dining area, and a kitchen in the background.

19. Cozy Heights Retreat | Baker's Kitchen & Sleeps 10

Cozy Heights Retreat | Baker's Kitchen & Sleeps 10
Windsor Heights
10.0 out of 10, Exceptional, (1 review)
"Stayed here with family and a dog. We had a few small issues, but the owner was responsive and easy to work with. "
United States
Greg M.
The price is £316
includes taxes & fees
28 Oct - 29 Oct
Cozy Heights Retreat | Baker's Kitchen & Sleeps 10
A modern house with a stone pillar, a front door with a glass panel, a bench, and a small garden.

20. Convenient functional quiet 5 bedroom 3 bath home in Clive.

Convenient functional quiet 5 bedroom 3 bath home in Clive.
Clive
10.0 out of 10, Exceptional, (22 reviews)
"Perfect stay! The home was spacious and clean and was just as great as depicted in the photos! The communications with the host were helpful and check in and check out was smooth,"
United States
Beth N.
The price is £569
includes taxes & fees
28 Oct - 29 Oct
Convenient functional quiet 5 bedroom 3 bath home in Clive.
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
"We had a great time with the grandkids. the pool was a hit!"
Sue 1-night trip
Posted 1 hour ago
Stoney Creek Hotel Des Moines - Johnston

Find out more about Winterset

Winterset Holiday Homes information

Number of reviews
744
Accommodation
165 Holiday Homes
Lowest Price
£118
Highest Price
£569