The Hotels in Osceola Iowa Blog:
Why Extended Stay Guests Choose Local

Alison Frank • September 8, 2025

Hotels in Osceola Iowa: 48 Hours of Parks, Food, and Fun

Imagine you're looking for something to do while you're staying at the best little hotel in Osceola, The Jeffreys Hotel Extended Stay. Think there's nothing to do here? Think again. We packed a fun 48 hour tour you can follow or bend to fit your days. Add your own stops. Swap a hike for a coffee. Slide in a fishing hour or a quiet museum visit. The possibilities are wide open and right here. Let’s take it minute by minute…

Check in: Night 1

3:10 p.m.

You check in to your favorite little hotel in Osceola, The Jeffreys Hotel Extended Stay. Think quiet rooms. Good Wi-Fi. Space to breathe. You drop your bag. You set the coffee. You exhale.

4:00 p.m.
Walk the square. Get your bearings. The courthouse sits at the center. The district is on the National Register, which is a nice way of saying the brick fronts and old cornices tell a story. You'll see new storefront updates mixed with older buildings.

5:30 p.m.
Easy crew-style dinner. If you want comfort food and quick service, try Family Table. Big plates. Friendly people. Good after a long drive.

7:00 p.m.
Sunset stretch at East Lake Park. It is close. Benches. Docks. A paved trail that loops back to town. Good shore fishing and a hard surface ramp if you brought gear. Keep it simple today. Save the longer hike for tomorrow.

9:15 p.m.
Lights out. Or stream a show and turn in early. (We've got Roku TV in here). You have a full day ahead.

Day 1

6:10 a.m.
The first fish hits and your bobber drops under the water at East Lake. Bluegill. Maybe a nice bass. Coffee in a travel mug. You're up before the wind.

7:45 a.m.
Breakfast at Mayberry’s Coffee House & Eatery on the square. Strong coffee. Breakfast sandwiches. House baked treats. Fast and friendly.

9:00 a.m.
Scenic drive to Winterset. Covered bridges. Courthouse square. If you're here in October, the Covered Bridge Festival fills the streets with booths and music from October 11-12. The parade starts at 3 p.m. on Sunday. Mark it down if your dates line up.

10:15 a.m.
Short photo loop to one or two bridges, then a slow walk around the square. Find a café. Take a seat. No rush.

12:30 p.m.
Back to Osceola for lunch at Iron Horse Neighborhood Grill. Burgers. Salads. Sit and recharge before the afternoon.

2:00 p.m.
Museum hour. On summer Sundays the Clarke County Historical Museum opens for a quiet walk through local history. If your timing's different, check hours first. The stained glass and local artifacts are worth a look.

3:30 p.m.
Simple errand run. Groceries. Sunscreen. Snacks. Then back to the hotel for a quick reset.

5:30 p.m.
Evening plan one. If you like live music and table games, Lakeside Hotel Casino has Saturday shows in September and special events during the month. If you're around on Sept 24, the Preacher Lawson show hits the event center at 7 p.m. Check the casino calendar to match your dates.

8:45 p.m.
Late bite back in town at Cuban Flavor. Or tuck in early. Tomorrow's your nature day.

Day 2

6:40 a.m.
Quiet loop around the water. Same lake. Different light. Or switch to the wooded trails for birds and a little climb.

8:15 a.m.
Second breakfast. If you missed Family Table on night one, go now. If you already tried it, circle back to Mayberry’s for a lighter start. Your call.

9:30 a.m.
Drive north to Stephens State Forest or continue to Banner Lakes at Summerset near Indianola. Both offer easy trails and places to sit by the water. Banner Lakes has short shoreline walks and simple parking. Perfect for a calm half day.

12:30 p.m.
Indianola winery stop. Summerset Winery offers tastings and relaxed patio time. Keep it responsible and linger over a small plate.

2:30 p.m.
Fall only idea ... Howell’s Pumpkin Patch in Cumming. Baby goats in early fall. Farmyard play. Pumpkin fields as the season turns. Hours run to 6 p.m. in September and October.

4:45 p.m.
Back to Osceola. If your dates land Sept 15 to 21, the Chamber’s Restaurant Week is a fun excuse to sample local menus. If you're here in late October, the Downtown Spooktacular brings costumes to the square. Check the Chamber calendar for the most current list.

6:15 p.m.
Dinner round two. Playa Margaritas Mexican Restaurant if you want a sit-down meal. If you're keeping it casual, try a pizza at Keller's or a quick taco night at Hermanos Lopez Taqueria. Keep the evening open.

7:45 p.m.
Nightcap at Revelton Distilling Co. Their tasting room hosts periodic live music on weekends and offers tours. It's right here in Osceola, which makes the return to your room easy.

9:30 p.m.
Walk the square one last time. Lights on the storefronts. Quiet streets. You're settled in.

That's your first 48 hours, simple and full. Take what you like and make it your own. If you find a new favorite stop, tell us at the front desk so we can share it. When you're ready for more, the town is waiting.

Simple packing list and notes

Fishing basics for the lake. Small tackle box. Iowa fishing license rules apply.
Shoes for short hikes. A light jacket if it is fall.
Reusable water bottle. Picnic kit.
A small cooler for winery snacks and pumpkin patch finds.