5/5 - Excellent
Verified traveler
We visited the bridges of Madison county and local wineries. Beautiful drives.
Winterset, IA
Travel Guide
Visit Winterset
Cobblestone Inn & Suites - Winterset, IA
1304 North 4th Avenue, Winterset, IA
The price is SAR 513 per night from Oct 6 to Oct 7
SAR 513
SAR 574 total
6 Oct - 7 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (672 reviews)
"Perfect. Quaint wonderful community"
Reviewed on 8 September 2025
Covered Bridge Inn
1312 Cedar Bridge Rd., Winterset, IA
The price is SAR 334 per night from Oct 3 to Oct 4
SAR 334
SAR 367 total
3 Oct - 4 Oct
includes taxes & fees
Stay at this motel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9/10 Wonderful! (732 reviews)
"It was reasonable."
Reviewed on 10 September 2025
Hotel Fort Des Moines, Curio Collection by Hilton
1000 Walnut St, Des Moines, IA
The price is SAR 523 per night from Sep 21 to Sep 22
SAR 523
SAR 586 total
21 Sep - 22 Sep
includes taxes & fees
Stay at this 4.5-star luxury hotel in Des Moines. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,014 reviews)
"The hotel is in a lovely, old building with great architecture. The room was clean. The bathroom was in disrepair with the shower head hanging in a broken bracket, which fell a few times in the middle of the night, waking us up. The faucet fixtures had the cover rings just hanging off the wall. The ..."
Reviewed on 9 September 2025
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.
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Des Moines
Book a stay at this family-friendly vacation home in Des Moines. Enjoy free WiFi, a fitness center, and laundry facilities. Our guests praise the helpful staff ...
9.2/10 Wonderful! (55 reviews)
"Thanks so much! We enjoyed the stay with our family"
Reviewed on 18 August 2025
Beautiful home minutes from downtown!
Des Moines
Stay at this vacation home in Des Moines. Enjoy laundry facilities and air conditioning. Popular attractions Casey's Center and Iowa State Fairgrounds are located ...
9.2/10 Wonderful! (16 reviews)
"This worked out great for us while we were in town for a wedding. Plenty of room for 4 of us and a dog!"
Reviewed on 24 August 2025
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom
Des Moines
Stay at this vacation home in Des Moines. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Casey's Center and Jordan Creek Town Center ...
9.4/10 Exceptional! (23 reviews)
"Wonderful property! Location was excellent and close to everything we were looking for. Home was super cute and we loved the hot tub and fire pit. Beds were comfy and I would highly recommend staying here! We will definitely stay here again!"
Reviewed on 23 August 2025
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.
Popular places to visit
Roseman Bridge
You can learn about the history of Winterset with a stop at Roseman Bridge. Make some time to visit the monuments while you're in the area.
Clark Tower
You can find out about the history of Winterset with a stop at Clark Tower. Make some time to visit the shops while you're in the area.
John Wayne Birthplace Museum
You can spend an afternoon browsing the exhibits at John Wayne Birthplace Museum in Winterset. While you're in the area, wander around the natural setting.
Madison County Courthouse
Madison County Courthouse is just one of the places to see in Winterset, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the natural setting.
The Winterset Stage
You can enjoy a show at The Winterset Stage during your stay in Winterset. Make some time to visit the shops while you're in the area.
Cedar Bridge
You can learn about the history of Winterset when you stop by Cedar Bridge. Make some time to visit the monuments while you're in the area.
Reviews of Winterset
4.6
Top Destination
5/5 - Excellent
Terri
Loved Winterset. John Wayne museum was nightlight. Enjoyed seeing the covered bridges. The downtown was so authentic...took you back in time. Beautiful old building. Beautiful parks. Hope to go back when the weather is nicer.
3/5 - Okay
Verified traveler
Very limited dining choices for an area with many wonderful sites to see
5/5 - Excellent
Verified traveler
Great place, we enjoyed our visit.
5/5 - Excellent
Patty
Loved the town, it was small but very nice.
4/5 - Good
Verified traveler
Beautiful town. Locals are very friendly and make you feel at home. The bridges are one of our favorite places to visit.
- Roseman Bridge
- John Wayne Birthplace Museum
- Madison County Courthouse
- The Winterset Stage
- Cedar Bridge
- Pammel State Park
- Clark Tower
- Hogback Bridge
- Holliwell Bridge
- Jordan Creek Town Center
- Drake University
- Blank Park Zoo
- Hoyt Sherman Place
- Living History Farms
- Val Air Ballroom
- Des Moines Art Center
- Merle Hay Mall
- West Glen Town Center
- Lauridsen Amphitheater
- Valley Junction
- Lakeside Casino
- Gray’s Lake Park
- Salisbury House
- Simpson College
- Mercy Medical Center West Lakes
- National Balloon Museum
- Walnut Woods State Park
- Osceola Country Club
- John and Mary Pappajohn Sculpture Park
- Raccoon River Park
- Water Works Park
