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

Holiday Homes in Winterset

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Our top choices for Winterset holiday homes

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 NZ$563
includes taxes & fees
30 Nov - 1 Dec
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

2. 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.
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

3. 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 NZ$697
includes taxes & fees
8 Nov - 9 Nov
Middlebrook Retreat, "Luxurious Retreat in Iowa's First Agrihood: Minutes to Des Moines & Steps to C...

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

Adel 4BR/Game Room, Park Nearby & Sleeps 12
Adel
8.8 out of 10, Excellent, (6 reviews)
"This suited our needs in preparation of our daughter’s wedding so our immediate family could all be together. Maybe the lawn could’ve been freshly mowed for easier outside games. The house was clean and nice and fit our needs. Thank you."
United States
Anna C.
The price is NZ$663
includes taxes & fees
17 Nov - 18 Nov
Adel 4BR/Game Room, Park Nearby & Sleeps 12

5. 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, (416 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 NZ$327
includes taxes & fees
5 Nov - 6 Nov
Beautiful Rustic Barn just waiting for you to kick back and relax.

6. Farmhouse Oasis

Farmhouse Oasis
Dallas Center
10.0 out of 10, Exceptional, (33 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 NZ$298
includes taxes & fees
9 Nov - 10 Nov
Farmhouse Oasis

7. 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 NZ$354
includes taxes & fees
5 Nov - 6 Nov
Spacious Farmhouse beautifully decorated waiting for laughs and memories

8. 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 NZ$321
includes taxes & fees
8 Nov - 9 Nov
The Hen House Country Living with Farm Life Appeal Indianola, IA

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

Spacious 4BR Home • WiFi • Family-Friendly • Waukee
Waukee
10.0 out of 10, Exceptional, (43 reviews)
"A very nice place! Throughly enjoyed my stay there!"
United States
Steven B.
The price is NZ$749
includes taxes & fees
21 Nov - 22 Nov
Spacious 4BR Home • WiFi • Family-Friendly • Waukee

10. Beautiful home minutes from downtown!

Beautiful home minutes from downtown!
Des Moines
9.2 out of 10, Wonderful, (49 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 NZ$464
includes taxes & fees
5 Nov - 6 Nov
Beautiful home minutes from downtown!

11. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (12 reviews)
"We absolutely loved our stay. The place was clean and comfortable. Very peaceful and quiet."
United States
Ana M.
The price is NZ$385
includes taxes & fees
10 Nov - 11 Nov
Adair Hideaway : Quiet Neighborhood - Fenced Yard

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, (24 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 NZ$472
includes taxes & fees
9 Nov - 10 Nov
Beautiful 3-bedroom house with AC in adorable Des Moines

13. •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 NZ$749
includes taxes & fees
22 Nov - 23 Nov
•Delightful 5b stay in Paradise!!•

14. 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 NZ$1,102
includes taxes & fees
5 Nov - 6 Nov
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

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)
"We really enjoyed our stay here. The owners were great about communication and were attentive to the needs/desires of our group. Our group was comprised of all different ages and the home had a little something to offer everyone: games for kids, outdoor sitting area for adults, etc. The kitchen was well stocked and the stay was very comfortable. We would definitely stay here again when back in the area!"
United States
Lindsey S.
The price is NZ$816
includes taxes & fees
5 Nov - 6 Nov
Walnut Row, Walk to Valley Junction, Sleeps 10+

16. Suburban Oasis with Hot Tub Spa

Suburban Oasis with Hot Tub Spa
Urbandale
10.0 out of 10, Exceptional, (39 reviews)
"Perfect location! Host responded quickly. Would book this home again."
United States
Daniel/Beth W.
The price is NZ$652
includes taxes & fees
22 Nov - 23 Nov
Suburban Oasis with Hot Tub Spa

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

Studio Suite w/ Jetted Tub | Free Breakfast!
West Des Moines
The price is NZ$269
includes taxes & fees
23 Nov - 24 Nov
Studio Suite w/ Jetted Tub | Free Breakfast!

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 NZ$481
includes taxes & fees
5 Nov - 6 Nov
Electric Velvet- 3 bedroom stay near downtown Des Moines

19. 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 NZ$474
includes taxes & fees
5 Nov - 6 Nov
3-bedroom townhome in serene West Des Moines with AC

20. Grain Bin and outdoor bar with countryside views, cows, & beautiful Iowa scenery

Grain Bin and outdoor bar with countryside views, cows, & beautiful Iowa scenery
Stuart
10.0 out of 10, Exceptional, (2 reviews)
"We had our daughter’s 5th birthday here and she LOVED it!! Such a fun and unique place to host family and friends 🩷The indoor and outdoor spaces make it ideal for gathering and celebrating. The owners thought of everything and were so accommodating! Definitely recommend to everyone!"
United States
Alyse D.
The price is NZ$551
includes taxes & fees
23 Nov - 24 Nov
Grain Bin and outdoor bar with countryside views, cows, & beautiful Iowa scenery
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

Winterset Holiday Homes information

Number of reviews
730
Accommodation
159 Holiday Homes
Lowest Price
NZ$269
Highest Price
NZ$1,102