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Search results; 24 places
24 places
Guest favorite
Guest favorite
Home in Winterset
The Legacy Stone House
1 queen bed
1 queen bed
Apr 19 – 24
Apr 19 – 24
$119
night
$119 per night
4.97 out of 5 average rating, 193 reviews
4.97 (193)
Guest favorite
Guest favorite
Home in Winterset
Debbie’s Komfy Diggs Winterset
2 beds
2 beds
May 12 – 17
May 12 – 17
$90
night
$90 per night
4.99 out of 5 average rating, 185 reviews
4.99 (185)
Guest favorite
Guest favorite
Apartment in Winterset
The Suite Iowa Life
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$85
night
$85 per night
4.94 out of 5 average rating, 280 reviews
4.94 (280)
Apartment in Winterset
Iowa Nice Winterset
3 beds
3 beds
May 5 – 10
May 5 – 10
$83
night
$83 per night
4.84 out of 5 average rating, 396 reviews
4.84 (396)
Guest favorite
Guest favorite
Cabin in Cumming
Iconic Iowa - A 1920 Built Country Cabin
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
$135
night
$135 per night
5.0 out of 5 average rating, 98 reviews
5.0 (98)
Guest favorite
Guest favorite
Guest suite in Winterset
2 BR fully furnished private condo
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$115
night
$115 per night
4.87 out of 5 average rating, 85 reviews
4.87 (85)
Guest favorite
Guest favorite
Home in Winterset
Rosehaven
4 beds
4 beds
May 12 – 17
May 12 – 17
$146
night
$146 per night
5.0 out of 5 average rating, 45 reviews
5.0 (45)
Guest favorite
Guest favorite
Farm stay in Winterset
Entire farmhouse in the country
5 beds
5 beds
Apr 28 – May 3
Apr 28 – May 3
$250
night
$250 per night
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Guest favorite
Guest favorite
Home in Winterset
The Holliwell House
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$315
$245
night
$245 per night, originally $315
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Guest favorite
Guest favorite
Place to stay in Winterset
Whimsical cabin nestled in the woods
1 king bed
1 king bed
May 26 – 31
May 26 – 31
$142
night
$142 per night
4.9 out of 5 average rating, 62 reviews
4.9 (62)
Guest favorite
Guest favorite
Home in Winterset
The Roost at Speckled Hen Farms.
4 beds
4 beds
Apr 20 – 25
Apr 20 – 25
$199
night
$199 per night
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Guest favorite
Guest favorite
Cabin in Winterset
Cabin on 10 Wooded Acres to Relax, Unwind & Gather
8 beds
8 beds
Jul 1 – 6
Jul 1 – 6
$460
night
$460 per night
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Guest favorite
Guest favorite
Home in Winterset
The Home Place
2 beds
2 beds
May 13 – 18
May 13 – 18
$114
night
$114 per night
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Guest favorite
Guest favorite
Home in Winterset
The Little Red House
4 beds
4 beds
Apr 23 – 28
Apr 23 – 28
$130
night
$130 per night
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favorite
Guest favorite
Farm stay in Winterset
Historic Stone Farm House & Venue
6 beds
6 beds
May 6 – 11
May 6 – 11
$225
night
$225 per night
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Guest favorite
Guest favorite
Home in Winterset
The Bungalow in Winterset
5 beds
5 beds
Apr 19 – 24
Apr 19 – 24
$207
night
$207 per night
5.0 out of 5 average rating, 58 reviews
5.0 (58)
Guest favorite
Guest favorite
Home in Earlham
Friendly Quarters
6 beds
6 beds
Apr 22 – 27
Apr 22 – 27
$173
night
$173 per night
4.95 out of 5 average rating, 82 reviews
4.95 (82)
Guest favorite
Guest favorite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
6 beds
6 beds
Apr 20 – 25
Apr 20 – 25
$175
night
$175 per night
5.0 out of 5 average rating, 57 reviews
5.0 (57)
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