Hot Winterset Cottage Rates

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Featured Cottages in Winterset

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

2 out of 5
Des Moines IA
The price is AU$311 per night from 12 Feb to 13 Feb
AU$311
12 Feb - 13 Feb
includes taxes & fees
With a stay at this cottage in Des Moines (Woodland Heights), you'll be within a 15-minute drive of Casey's Center and Iowa State Fairgrounds.
Opens in a new windowCozy Cottage Near Downtown Walkable to Dining and Boutique Shopping
Family-friendly Des Moines Retreat w/ Patio!

Family-friendly Des Moines Retreat w/ Patio!

3 out of 5
Des Moines IA
With a stay at this cottage in Des Moines (Drake), you'll be within a 15-minute drive of Casey's Center and Iowa State Fairgrounds.
Opens in a new windowFamily-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 IA
With a stay at this cottage in Winterset, you'll be a 4-minute walk from Madison County Courthouse and 7 minutes by foot from John Wayne Birthplace Museum.
Opens in a new windowCharming Winterset Vacation Rental w/ Yard & Patio
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Secluded St Charles Cabin w/ Gas Grill + Fire Pit!

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

2 out of 5
Saint Charles IA
With a stay at this cottage in Saint Charles, you'll be 21.7 mi (35 km) from Jordan Creek Town Center and 30.3 mi (48.7 km) from Iowa Events Center.
Opens in a new windowSecluded St Charles Cabin w/ Gas Grill + Fire Pit!
Raccoon River Retreat: Indoor Pool & Outdoor Fun!

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

3 out of 5
Adel IA
With a stay at this cottage in Adel, you'll be within a 10-minute drive of Penoach Winery and Island Park.
Opens in a new windowRaccoon River Retreat: Indoor Pool & Outdoor Fun!
1 Mi to Golf: Quiet Waukee Home w/ Fireplace!

1 Mi to Golf: Quiet Waukee Home w/ Fireplace!

3 out of 5
Waukee IA
With a stay at this cottage in Waukee, you'll be within a 15-minute drive of Jordan Creek Town Center and The Triangle.
Opens in a new window1 Mi to Golf: Quiet Waukee Home w/ Fireplace!
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 IA
With a stay at this cottage in West Des Moines, you'll be within a 10-minute drive of Casey's Center and Jordan Creek Town Center.
Opens in a new window1 Mi to Valley Junction: Pet-friendly Iowa Home
Pet-friendly Des Moines Home w/ Fenced Yard!

Pet-friendly Des Moines Home w/ Fenced Yard!

3 out of 5
5901 SE 25th St Des Moines IA
With a stay at this cottage in Des Moines, you'll be within a 15-minute drive of Iowa Events Center and Casey's Center.
Opens in a new windowPet-friendly Des Moines Home w/ Fenced Yard!
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!

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

3 out of 5
Urbandale IA
Located in Urbandale, this cottage is within a 15-minute drive of Casey's Center and Jordan Creek Town Center.
Opens in a new windowPet-friendly Urbandale Home ~ 8 Mi to Des Moines!
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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
10 Cottages
Lowest Price
AU$113
Highest Price
AU$311
Popular accommodation
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping, Family-friendly Des Moines Retreat w/ Patio!, Charming Winterset Vacation Rental w/ Yard & Patio, Secluded St Charles Cabin w/ Gas Grill + Fire Pit!, Raccoon River Retreat: Indoor Pool & Outdoor Fun!, 1 Mi to Golf: Quiet Waukee Home w/ Fireplace!, 1 Mi to Valley Junction: Pet-friendly Iowa Home, Pet-friendly Des Moines Home w/ Fenced Yard!, Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!

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$142 per night from 16 Feb to 17 Feb
AU$142
16 Feb - 17 Feb
includes taxes & fees
Located in Winterset, Cobblestone Inn & Suites - Winterset, IA is in a rural location, within a 5-minute drive of Madison County Courthouse and John Wayne Birthplace ...
Opens in a new windowCobblestone Inn & Suites - Winterset, IA
Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
The price is AU$213 per night from 25 Feb to 26 Feb
AU$213
25 Feb - 26 Feb
includes taxes & fees
With a stay at Hotel Fort Des Moines, Curio Collection by Hilton, you'll be centrally located in Des Moines, within a 5-minute drive of Iowa Events Center and ...
Opens in a new windowHotel Fort Des Moines, Curio Collection by Hilton
Home2 Suites by Hilton Des Moines at Drake University

Home2 Suites by Hilton Des Moines at Drake University

3 out of 5
2650 University Ave. Des Moines IA
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 15 Feb to 16 Feb
AU$141
15 Feb - 16 Feb
includes taxes & fees
With a stay at Home2 Suites by Hilton Des Moines at Drake University in Des Moines (Drake), you'll be steps from Drake University and a 4-minute drive from Iowa ...
Opens in a new windowHome2 Suites by Hilton Des Moines at Drake University
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Sonesta Simply Suites Des Moines

Sonesta Simply Suites Des Moines

2 out of 5
7625 Office Plaza Dr N West Des Moines IA
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 15 Feb to 16 Feb
AU$113
15 Feb - 16 Feb
includes taxes & fees
Located in West Des Moines, Sonesta Simply Suites Des Moines is in the entertainment district, a 3-minute drive from Jordan Creek Town Center and 8 minutes from ...
Opens in a new windowSonesta Simply Suites Des Moines
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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.