999 places in Winterset

Guest favorite
Home in Winterset
Debbie’s Komfy Diggs Winterset
2 beds
Apr 1 – 6
4.99 out of 5 average rating, 179 reviews
Guest favorite
Apartment in Winterset
The Suite Iowa Life
1 queen bed
Apr 1 – 6
4.94 out of 5 average rating, 279 reviews
Guest favorite
Home in Winterset
Rosehaven
4 beds
May 4 – 9
5.0 out of 5 average rating, 44 reviews
Guest favorite
Guest suite in Winterset
2 BR fully furnished private condo
3 beds
Apr 1 – 6
4.87 out of 5 average rating, 83 reviews
Guest favorite
Cabin in Winterset
Cabin on 10 Wooded Acres to Relax, Unwind & Gather
8 beds
May 31 – Jun 5
4.98 out of 5 average rating, 47 reviews
Guest favorite
Home in Winterset
The Legacy Stone House
1 queen bed
Jun 1 – 6
4.97 out of 5 average rating, 192 reviews
Guest favorite
Home in Winterset
The Home Place
2 beds
Apr 4 – 9
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Winterset
The Roost at Speckled Hen Farms.
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 42 reviews
Guest favorite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
4 beds
Apr 1 – 6
4.98 out of 5 average rating, 40 reviews
Guest favorite
Home in Winterset
The Bungalow in Winterset
5 beds
May 5 – 10
5.0 out of 5 average rating, 58 reviews
Guest favorite
Apartment in Winterset
Iowa Nice Winterset
3 beds
Apr 6 – 11
4.84 out of 5 average rating, 395 reviews
Guest favorite
Place to stay in Winterset
Whimsical cabin nestled in the woods
1 king bed
Apr 14 – 19
4.9 out of 5 average rating, 60 reviews
Guest favorite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
6 beds
Apr 8 – 13
5.0 out of 5 average rating, 54 reviews
Guest favorite
Guesthouse in Winterset
Luxury Guest Home in Beautiful Madison County
6 beds
Apr 1 – 6
5.0 out of 5 average rating, 23 reviews
Guest favorite
Farm stay in Winterset
Historic Stone Farm House & Venue
6 beds
Apr 1 – 6
4.97 out of 5 average rating, 32 reviews
Guest favorite
Home in Winterset
The Little Red House
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 14 reviews
Guest favorite
Farm stay in Winterset
Entire farmhouse in the country
5 beds
Apr 1 – 6
4.95 out of 5 average rating, 21 reviews
Guest favorite
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
1 king bed
May 6 – 11
5.0 out of 5 average rating, 18 reviews