
Holiday rentals in Winterset
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Top-rated holiday rentals in Winterset
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Winterset
Top guest favourite

Home in Philo
4.98 out of 5 average rating, 65 reviewsRiver R&R
SheriRating, 5 stars4 days ago
We had a wonderful stay at this beautiful a d spacious home while in town for a family wedding. Check in was super easy and never had any issues during our week long stay, so we never had to contact hosts. We would highly recommend.
Top guest favourite

Home in Triadelphia
5 out of 5 average rating, 27 reviewsThe Crow's Nest - scenic views & a hot tub
CatherineRating, 5 stars3 days ago
An absolutely beautiful cabin with a perfect layout for a getaway! The kitchen had everything we needed and the cabin was charming and comfortable. We enjoyed cooking while listening to the record player and then soaked in the hot tub under the stars. The location was private and quiet, yet close to plenty of things to do! We will absolutely be back and highly recommend this cabin! Nice personal touches to spoil us a little as well were much appreciated!
Superhost

Home in Cambridge
4.81 out of 5 average rating, 68 reviews3BR Country Escape (sleeps 6), tree-lined 3 acres
DanaRating, 5 stars2 weeks ago
The house was exactly as described. As an older building, it was fun to explore the quaint features throughout! So many light switches 😁. It was spacious with several gathering spaces, which was perfect for playing games and spending time together. The wrap around drive made it easy for family to come and go on their own schedule. Check in and check out was effortless. We loved the proximity to the interstate and the grounds were lovely. Thank you for your hospitality!
Top guest favourite

Farm stay in Port Washington
5 out of 5 average rating, 60 reviewsGoosefoot School- Renovated schoolhouse on a farm
BetsyRating, 5 stars5 days ago
This is a beautiful, peaceful place, easy to find off the interstate and very comfortable. It was a great place to overnight on a road trip, very good value compared to a hotel, and such a slice of local history. We are hoping to be back for a longer stay!
Superhost

Home in Big Prairie
5 out of 5 average rating, 4 reviewsStillwater Retreat | Private Pond w/ Kayaking
DavidRating, 5 stars1 week ago
Stunning. Really...no...REALLY!!! Stop scrolling, book it. Secluded retreat to detach from the world and recharge. The pictures are spot on. The seclusion is second to none.
Guest favourite

Home in Barnesville
5 out of 5 average rating, 14 reviewsNeva have I ever!
MichaelRating, 5 stars2 weeks ago
Perfect spot to stay in Barnesville. Hosts were very accommodating and helpful. Thanks for hosting our family!
Guest favourite

Campsite in Cambridge
5 out of 5 average rating, 22 reviewsGlamplyfe Nature Experience: A-Frames on Lakefront
AllisonRating, 5 stars2 days ago
Great spot to enjoy nature! The staff onsite were very helpful and responsive.
Top guest favourite

Yurt in Middlebourne
4.96 out of 5 average rating, 25 reviewsBigfoot Ridge Glamping got Squatched!
JenniferRating, 5 stars1 day ago
Traveling to this magical place takes you on a winding road through the scenic countryside. When I arrived, Bethany came to greet me with a friendly smile and a warm heart. She is a gracious and knowledgeable host. Their property was Bigfoot-ified and you can tell that she and her husband, Brock, put a lot of thought into every detail of this venture. The yurt was so much bigger then I imagined and it was intentionally decorated with that extra special Squatchy vibe. Bethany had the AC on, which made things very comfortable, and the bed was a dream to sleep in. At night, this place came alive with the soft glow of colorful lights, which I loved. The bathroom was spacious, clean, and had everything you need in case you forgot something. The shower had excellent pressure and plenty of hot water. The soft-sided hot tub was perfect after 7 hours of driving, and I got to watch the full moon rise over the ridge. It was a memorable, positive experience, and truly a must-stay destination!
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