Hot Winterset Cottage Rates

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Featured Cottages in Winterset

Family-friendly Des Moines Retreat w/ Patio!

Family-friendly Des Moines Retreat w/ Patio!

3 out of 5
Des Moines
With a stay at this cottage in Des Moines (Drake), you'll be within a 15-minute drive of Iowa State Fairgrounds and Jordan Creek Town Center.
Family-friendly Des Moines Retreat w/ Patio!
Charming Winterset Vacation Rental w/ Yard & Patio

Charming Winterset Vacation Rental w/ Yard & Patio

3 out of 5
Winterset
With a stay at this cottage in Winterset, you'll be a 5-minute walk from Madison County Courthouse and 7 minutes by foot from John Wayne Birthplace Museum.
Charming Winterset Vacation Rental w/ Yard & Patio
Secluded St Charles Cabin w/ Gas Grill + Fire Pit!

Secluded St Charles Cabin w/ Gas Grill + Fire Pit!

2 out of 5
Saint Charles
With a stay at this cottage in Saint Charles, you'll be 21.8 mi (35.1 km) from Jordan Creek Town Center and 9.2 mi (14.7 km) from Holliwell Bridge.
Secluded St Charles Cabin w/ Gas Grill + Fire Pit!
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Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!

Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!

3 out of 5
Urbandale
With a stay at this cottage in Urbandale, you'll be within a 15-minute drive of Jordan Creek Town Center and Buccaneer Arena.
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
Raccoon River Retreat: Indoor Pool & Outdoor Fun!

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

3 out of 5
Adel
With a stay at this cottage in Adel, you'll be 20.6 mi (33.1 km) from Jordan Creek Town Center and 8.3 mi (13.4 km) from Brenton Arboretum.
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
'the Barn' Secluded Home 7 Mi to Afton Lake!

'the Barn' Secluded Home 7 Mi to Afton Lake!

2 out of 5
Afton
With a stay at this cottage in Afton, you'll be 15.8 mi (25.5 km) from Holy Spirit Catholic Parish and 16.2 mi (26.1 km) from McKinley Park.
'the Barn' Secluded Home 7 Mi to Afton Lake!
'the Lodge' Spacious Afton Cabin Near Fishing!

'the Lodge' Spacious Afton Cabin Near Fishing!

2 out of 5
Afton
With a stay at this cottage in Afton, you'll be 15.8 mi (25.5 km) from Holy Spirit Catholic Parish and 16.2 mi (26.1 km) from McKinley Park.
'the Lodge' Spacious Afton Cabin Near Fishing!
Pet-friendly Des Moines Home w/ Fenced Yard!

Pet-friendly Des Moines Home w/ Fenced Yard!

3 out of 5
Des Moines
With a stay at this cottage in Des Moines, you'll be within a 5-minute drive of Southridge Mall and Fort Des Moines Museum.
Pet-friendly Des Moines Home w/ Fenced Yard!
1 Mi to Valley Junction: Pet-friendly Iowa Home

1 Mi to Valley Junction: Pet-friendly Iowa Home

3 out of 5
West Des Moines
With a stay at this cottage in West Des Moines, you'll be within a 15-minute drive of Jordan Creek Town Center and Iowa State Fairgrounds.
1 Mi to Valley Junction: Pet-friendly Iowa Home
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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.

Winterset Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winterset will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winterset definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winterset, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winterset Cottages essential information

Accommodation
12 Cottages
Lowest Price
AU$84
Highest Price
AU$181
Popular accommodation
Family-friendly Des Moines Retreat w/ Patio!, Charming Winterset Vacation Rental w/ Yard & Patio, Secluded St Charles Cabin w/ Gas Grill + Fire Pit!, Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!, Raccoon River Retreat: Indoor Pool & Outdoor Fun!, 'the Barn' Secluded Home 7 Mi to Afton Lake!, 'the Lodge' Spacious Afton Cabin Near Fishing!, Pet-friendly Des Moines Home w/ Fenced Yard!, 1 Mi to Valley Junction: Pet-friendly Iowa Home

Top trending hotels in Winterset

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue, Winterset, IA
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 24 Jan to 25 Jan
AU$161
includes taxes & fees
24 Jan - 25 Jan 2025
Located in Winterset, Cobblestone Inn & Suites - Winterset, IA is in a rural location, within a 5-minute drive of The Winterset Stage and Madison County ...
Cobblestone Inn & Suites - Winterset, IA
Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
The price is AU$104 per night from 25 Dec to 26 Dec
AU$104
includes taxes & fees
25 Dec - 26 Dec
Located in Winterset, Covered Bridge Inn is within a 5-minute drive of The Winterset Stage and John Wayne Birthplace Museum.
Covered Bridge Inn
Days Inn by Wyndham West Des Moines / Clive

Days Inn by Wyndham West Des Moines / Clive

2 out of 5
1600 NW 114th St, Clive, IA
Fully refundableReserve now, pay when you stay
The price is AU$84 per night from 4 Jan to 5 Jan
AU$84
includes taxes & fees
4 Jan - 5 Jan 2025
With a stay at Days Inn by Wyndham West Des Moines / Clive in Clive, you'll be near the airport, within a 10-minute drive of Jordan Creek Town Center and Clive ...
Days Inn by Wyndham West Des Moines / Clive
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Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston

2.5 out of 5
5291 Stoney Creek Court, Johnston, IA
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 25 Dec to 26 Dec
AU$181
includes taxes & fees
25 Dec - 26 Dec
Located in Johnston, Stoney Creek Hotel Des Moines - Johnston is in the suburbs, within a 15-minute drive of Jordan Creek Town Center and Drake University.
Stoney Creek Hotel Des Moines - Johnston
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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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^Subject to availability and chosen travel dates.