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Our top choices for Winterset pet-friendly hotels

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA
2.5 star property
Winterset
9.2 out of 10, Wonderful, (712)
"Great place to stay. "
United States
Steve
The price is Rp1.359.660
Rp1.522.839 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cobblestone Inn & Suites - Winterset, IA

Covered Bridge Inn

Covered Bridge Inn
2.5 star property
Winterset
9.0 out of 10, Wonderful, (769)
"Breakfast was top notch for the price."
United States
Raymond
The price is Rp1.643.726
Rp1.840.953 total
includes taxes & fees
1 Jan - 2 Jan 2026
Covered Bridge Inn

AmericInn by Wyndham Stuart

AmericInn by Wyndham Stuart
2.5 star property
Stuart
8.4 out of 10, Very good, (526)
"Was clean and nice."
United States
Christopher
The price is Rp1.403.733
Rp1.639.264 total
includes taxes & fees
9 Jan - 10 Jan 2026
AmericInn by Wyndham Stuart

Lakeside Hotel Casino

Lakeside Hotel Casino
3.0 star property
Osceola
8.2 out of 10, Very good, (1002)
"Room was clean, staff were pleasant."
United States
Yvette
The price is Rp1.207.344
Rp1.585.363 total
includes taxes & fees
5 Jan - 6 Jan 2026
Lakeside Hotel Casino

Evergreen Inn

Evergreen Inn
2.5 star property
Osceola
9.0 out of 10, Wonderful, (692)
"The room was very clean and comfortable. Kari was super friendly and helpful as we checked in. "
United States
Randy
The price is Rp875.446
Rp980.433 total
includes taxes & fees
9 Jan - 10 Jan 2026
Evergreen Inn

Super 8 by Wyndham Osceola IA

Super 8 by Wyndham Osceola IA
2.0 star property
Osceola
8.6 out of 10, Excellent, (237)
"Very convenient location and wonderful staff!"
United States
Sandra
The price is Rp1.341.680
Rp1.502.682 total
includes taxes & fees
9 Jan - 10 Jan 2026
Super 8 by Wyndham Osceola IA

Quality Inn Osceola

Quality Inn Osceola
2.5 star property
Osceola
8.6 out of 10, Excellent, (64)
"Great place to stay!!!"
United States
Cynthia
The price is Rp1.509.390
Rp1.690.517 total
includes taxes & fees
1 Jan - 2 Jan 2026
Quality Inn Osceola

Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West
2.5 star property
West Des Moines
9.0 out of 10, Wonderful, (1005)
"Room was clean, staff was courteous and the bed was comfortable. "
United States
Craig
The price is Rp1.268.726
Rp1.420.973 total
includes taxes & fees
25 Jan - 26 Jan 2026
Fairfield Inn and Suites by Marriott Des Moines West

La Quinta Inn & Suites by Wyndham Des Moines West Clive

La Quinta Inn & Suites by Wyndham Des Moines West Clive
3.0 star property
Clive
8.6 out of 10, Excellent, (1005)
"Very clean with a great breakfast. My kiddos loved the pool!"
United States
Erica
The price is Rp1.190.406
Rp1.333.254 total
includes taxes & fees
25 Jan - 26 Jan 2026
La Quinta Inn & Suites by Wyndham Des Moines West Clive

Hotel Pommier Indianola

Hotel Pommier Indianola
2.5 star property
Indianola
9.2 out of 10, Wonderful, (438)
"Loved it! Quaint and perfect stay! "
United States
Kara
The price is Rp1.240.130
Rp1.388.871 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hotel Pommier Indianola
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.

Top Winterset Hotel Reviews

Frequently asked questions

What's the best dog-friendly accommodation option in Winterset?
Cobblestone Inn & Suites - Winterset, IA is a top dog-friendly hotel, and offers a restaurant along with free WiFi for its human guests. Covered Bridge Inn is another good option for a stay with your pet.
What's the best time of year to travel to Winterset with my pet?
When you travel with your pet, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winterset are January, February, November and March, with each month seeing an average of 22 cm of snowfall.
What is there to see and do with your pet in Winterset?
See the local sights and visit John Wayne Birthplace Museum and Clark Tower. While you're there, make sure you don't miss Cedar Bridge and Holliwell Bridge.