We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 places in Winterset

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

The home you selected

Guest favorite

Home in Winterset

Holliwell Bridge Retreat Private & Cozy-Sleeps 12

12 guests5 bedrooms7 beds2.5 baths

Jun 10 – 15

More

Jun 10 – 15

More

ﺩ.ﺇ7,361 for 5 nights

for 5 nights

Explore more homes

Superhost

Home in Winterset

Covered Bridge Haven

Free cancellation

Jun 17 – 22

ﺩ.ﺇ4,805 for 5 nights

for 5 nights

New place to stay

Guest favorite

Apartment in Winterset

Luxury 2 Bed/2 Bath Condo

1 queen bed

Jun 16 – 21

ﺩ.ﺇ2,334 for 5 nights

for 5 nights

5.0 out of 5 average rating, 10 reviews

Top guest favorite

Home in Winterset

The Little Red House

Free cancellation

Jun 24 – 29

ﺩ.ﺇ2,798 for 5 nights

for 5 nights

5.0 out of 5 average rating, 33 reviews

Top guest favorite

Loft in Winterset

Aerie Loft Apartment with view that sleeps 7

Free cancellation

Jun 30 – Jul 5

ﺩ.ﺇ3,982 for 5 nights

for 5 nights

5.0 out of 5 average rating, 84 reviews

Guest favorite

Home in Winterset

Rosehaven

Free cancellation

Jun 29 – Jul 4

ﺩ.ﺇ3,272 for 5 nights

for 5 nights

4.99 out of 5 average rating, 90 reviews

Top guest favorite

Home in Winterset

Debbie’s Komfy Diggs Winterset

Free cancellation

Jun 22 – 27

ﺩ.ﺇ2,067 for 5 nights

for 5 nights

4.98 out of 5 average rating, 254 reviews

Guest favorite

Apartment in Winterset

Iowa Nice Winterset

Free cancellation

Jun 1 – 6

ﺩ.ﺇ1,616 for 5 nights

for 5 nights

4.85 out of 5 average rating, 434 reviews

Top guest favorite

Home in Winterset

The Legacy Stone House

Free cancellation

Jun 22 – 27

ﺩ.ﺇ2,583 for 5 nights

for 5 nights

4.96 out of 5 average rating, 256 reviews

Guest favorite

Guest suite in Winterset

2 BR fully furnished private condo

Free cancellation

Jun 7 – 12

ﺩ.ﺇ2,690 for 5 nights

for 5 nights

4.87 out of 5 average rating, 112 reviews

Top guest favorite

Home in Winterset

Renovated Cottage: 3 blocks to Winterset square

Free cancellation

Jul 10 – 15

ﺩ.ﺇ3,552 for 5 nights

for 5 nights

5.0 out of 5 average rating, 29 reviews

Top guest favorite

Apartment in Winterset

The Suite Iowa Life

1 queen bed

Jun 22 – 27

ﺩ.ﺇ1,840 for 5 nights

for 5 nights

4.94 out of 5 average rating, 337 reviews

Top guest favorite

Home in Winterset

Hygge House in the ❤️ of historic Winterset

Free cancellation

Jul 8 – 13

ﺩ.ﺇ4,090 for 5 nights

for 5 nights

4.98 out of 5 average rating, 56 reviews

Top guest favorite

Home in Winterset

Charming Winterset Vacation Rental w/ Yard & Patio

5 beds

Jun 27 – Jul 2

ﺩ.ﺇ3,436 for 5 nights

for 5 nights

5.0 out of 5 average rating, 15 reviews

Top guest favorite

Tent in Winterset

Glamping Flower Farm Stay- PepperHarrow

1 king bed

Jun 8 – 13

ﺩ.ﺇ2,690 for 5 nights

for 5 nights

5.0 out of 5 average rating, 31 reviews

Top guest favorite

Home in Winterset

The Home Place

2 beds

Jun 22 – 27

ﺩ.ﺇ3,121 for 5 nights

for 5 nights

5.0 out of 5 average rating, 34 reviews

Top guest favorite

Farm stay in Winterset

Entire farmhouse in the country

Free cancellation

Jun 1 – 6

ﺩ.ﺇ6,329 for 5 nights

for 5 nights

4.98 out of 5 average rating, 44 reviews

Room in Winterset

Stay with Laresa

Historic Judge Lewis House - Judge Lewis Room

Jun 1 – 6

ﺩ.ﺇ3,121 for 5 nights

for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favorite

Guest suite in Van Meter

Bougie Marsh w/100" TV, swings & recliners

3 beds

Jun 8 – 13

ﺩ.ﺇ1,812 for 5 nights

for 5 nights

5.0 out of 5 average rating, 6 reviews

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.

Now you’ll see one price for your trip, all fees included.