The Best Hotels with a Pool in Winterset from $65 in 2026

Q: What are some accommodations with pools in Winterset?

Cobblestone Inn & Suites - Winterset, IA : Hotel located near Casey's Center. Offers buffet, an indoor pool, and complimentary wired internet access. Covered Bridge Inn : Features an indoor pool, an outdoor pool, and a snack bar/deli. Hotel Fort Des Moines, Curio Collection by Hilton : Hotel located near Jordan Creek Town Center. Offers a snack bar/deli, an indoor pool, and daily. Sonesta Simply Suites Des Moines : Hotel, 6-minute walk from Jordan Creek Town Center. Provides a snack bar/deli, an indoor pool, and buffet. Home2 Suites by Hilton Des Moines at Drake University : Hotel located near Jordan Creek Town Center. Features an indoor pool, an outdoor pool, and buffet.

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Our top choices for Winterset hotels with a pool

Lakeside Hotel Casino, a Travelodge by Wyndham

Osceola

Retreat to an all-seasons indoor pool and fitness center at this lakeside hotel where every swim is a refreshing escape.

$84 nightly

Mar 4 - Mar 5

Total with taxes and fees

AmericInn by Wyndham Osceola

Osceola

Float in year-round bliss at this countryside hotel with a pristine indoor pool and hot tub.

$100 nightly

Mar 22 - Mar 23

Total with taxes and fees

Evergreen Inn

Osceola

Dive into refreshing poolside bliss with access to a nearby outdoor swimming spot.

$58 nightly

Mar 3 - Mar 4

Total with taxes and fees

Tru By Hilton Grimes Des Moines

Grimes

$81 nightly

Mar 19 - Mar 20

Total with taxes and fees

Drury Inn & Suites West Des Moines

West Des Moines

Soak in splendid relaxation at this hotel's dual-pool paradise, where indoor and outdoor aquatic havens await.

$100 nightly

Mar 8 - Mar 9

Total with taxes and fees

Quality Inn Osceola

Osceola

Splash into a serene indoor oasis at this centrally-located hotel with extended pool hours.

$90 nightly

Mar 3 - Mar 4

Total with taxes and fees

Hampton Inn & Suites West Des Moines/SW Mall Area

West Des Moines

Splash into serenity at this indoor pool oasis with adult-focused swim hours and hot tub relaxation.

$89 nightly

Mar 8 - Mar 9

Total with taxes and fees

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

West Des Moines

Dive into year-round swimming bliss at this West Des Moines hotel with an indoor pool and fitness center.

$97 nightly

Mar 8 - Mar 9

Total with taxes and fees

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Choose what matters most at hotels with a pool in Winterset

Breakfast included

Hot tub

Top Winterset Hotel Reviews

Drury Inn & Suites West Des Moines

10/10 Excellent

"Very nice hotel. Clean, great staff and convenient location. Will definitely stay again!"

Frequently asked questions

What are some accommodations with pools in Winterset?

Cobblestone Inn & Suites - Winterset, IA: Hotel located near Casey's Center. Offers buffet, an indoor pool, and complimentary wired internet access. Covered Bridge Inn: Features an indoor pool, an outdoor pool, and a snack bar/deli. Hotel Fort Des Moines, Curio Collection by Hilton: Hotel located near Jordan Creek Town Center. Offers a snack bar/deli, an indoor pool, and daily. Sonesta Simply Suites Des Moines: Hotel, 6-minute walk from Jordan Creek Town Center. Provides a snack bar/deli, an indoor pool, and buffet. Home2 Suites by Hilton Des Moines at Drake University: Hotel located near Jordan Creek Town Center. Features an indoor pool, an outdoor pool, and buffet.

What is there to see and do in Winterset?

Take in the natural beauty with a stop at Pammel State Park. Discover sights such as John Wayne Birthplace Museum, Roseman Bridge, and Clark Tower during your stay.

When is the best time to book a hotel with a pool in Winterset?

You may want to consider a place to stay that has an outdoor pool if you plan to visit Winterset in the hottest months of July, August, or June when the average temperature is 72°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 29°F.

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Our top choices for Winterset hotels with a pool