top of page
  • aliciaunderleenels

Last Minute Deals For A Fun Fall Getaway In The Midwest

Updated: Apr 29, 2021

Autumn is in full swing, but there’s still time for a fall getaway. Midwestern hotels have some great deals on all the fall experiences you’ve been craving, from ghosts stories and fall foliage tours to apple picking and spa getaways.

Many of these deals are for a limited time only, but the resorts, hotels and bed and breakfasts listed here are destinations in and of themselves. So even if you can’t travel this year, it’s worth bookmarking these properties for future trips.

Here are a few of the most fun deals for a Midwestern fall getaway.

Spooky history in Deadwood, South Dakota

The historic downtown looks much like it did when outlaws, gamblers, prospectors and gunslingers like Wild Bill Hickok and Calamity Jane roamed the streets. (Okay, technically, they’re still here — they reside permanently Mount Moriah Cemetery.)  Businessman Seth Bullock (made famous by the HBO series and film) is there too.

Learn spooky stories from the city’s wild west/gold rush past when you book the Deadwood Heroes and Villains vacation package. Valid now through December 30, 2019, it includes a visit to the cemetery, a Ghost Tour at the Bullock Hotel, and two nights lodging at your choice of several Deadwood hotels. Free admission to the Days of 76 Museum and The Adams Museum are included too.

You can still gamble in Deadwood, just like back in  the day. And I definitely recommend ordering whiskey at Saloon #10 American Whiskey Bar. Not only is this the very spot where Wild Bill Hickok was murdered (perfect for the history nerds like me), it also carries 150 varieties of whiskey, Scotch and bourbon for the whiskey geeks of the world.

A hiking and spa getaway in Geneva, Ohio

Lake House Inn Resort is nestled along the shore of Lake Erie, about an hour from Cleveland in Ohio’s wine country. The suites, cottages and beach house rentals have a cozy, upscale bed and breakfast vibe and water views. The spa offers a comprehensive menu of massages, body treatments, facials, manicures, pedicures and waxing services. With all that, plus a farm to table restaurant, wine from the boutique winery, and the option to have treats like craft beer and local cheeseboards delivered right to your room, who’d want to leave?

If you can tear yourself away from the relaxation long enough to get a little fresh air and exercise, the Fall Harvest Experience (available through November 23, 2019) is a great option. It includes an overnight stay, a bottle of apple cider in your room upon arrival and a full breakfast the next morning. You’ll also get a pass to visit Brant’s Apple Orchard, where you can hike along the orchard and vineyard trails, and a map to visit the area’s many covered bridges. The nearby  Smolen Gulf Bridge is the longest in the country.

Technically, spa services aren’t included in this package, but the spa does offer a pumpkin mani pedi and a pumpkin and fig facial seasonally. What could be more fall themed than that?

A family fall getaway in Ridgedale, Missouri

I fell in love with the Missouri Ozarks when I was working on a story there last fall, so I love the idea of disappearing to Big Cedar Lodge for a few days of autumn magic. It’s rustic, it’s remote and the sprawling grounds (so large that complimentary shuttle service around the resort is a featured amenity) look gorgeous.

You honestly never need to leave. Grab a drink in a casual bar or the upscale wine cellar and whiskey room. Try one of the impressive range of restaurants that serve everything from homestyle Southern cooking to contemporary Mexican cuisine. I’m pretty sure I could spend all day in the spa alone. There’s an indoor grotto pool with underwater lounges (okay, I’m intrigued), saunas, steam rooms and a cold therapy ice room.

Guests can enjoy Cedar Fest every Saturday afternoon in October. There are all the family-friendly fall classics you love, like pumpkin picking, hay rides, crackling bonfires and free hot cocoa and popcorn, as well as wild card activities like a mechanical bull. You’ll also find an impressive array of artistic activities, like pumpkin decorating, pottery painting and tie-dying sessions.

Pumpkin Picking in Bismarck, North Dakota

Papa’s Pumpkin Patch has been voted one of the best pumpkin patches in the U.S. When you book the Papa’s Pumpkin Patch Package (say that five times fast), you’ll get a room at Hampton Inn and Suites with two queen beds, pumpkin patch admission for four, five pumpkin patch activity tickets and four cookies, just for fun.

You need to act quickly though. The package is only available through October 19, 2019.

When you’re all pumpkined out, the hands-on Gateway to Science center is right next door. The hotel has an indoor pool and hot tub that are perfect for families. There’s a free continental breakfast the next day too, which is good if you’re on a budget.

Leaf peeping by bike in Milwaukee, Wisconsin

The Kimpton Journeyman Hotel is located in the heart of the historic Third Ward, one of my favorite neighborhoods in Milwaukee. There are tons of cool shops, breweries, restaurants and river views, all within walking distance.

The pet-friendly hotel offers sweet (and complimentary) add-ons like coffee and tea every morning and wine and growlers of local craft beer during nightly social hours. There’s a free yoga mat in every room, a 24-hour fitness center, bikes for exploring, in-room ice cream delivery and local experts on hand to send you to the coolest spots that have popped up since your last visit.

You can truly see Milwaukee like a local when you book the Leaf Peep + Bike Package. You’ll score two bikes to explore The Oak Leaf Trail, over 100 miles of paved paths and trails that snake throughout the city. The hotel will pack you a picnic of savory snacks from Tre Rivali in a Journeyman leather backpack handmade by Milwaukee artist Heather Hembracht.

Apple picking in Saugatuck, Michigan

Located on the shore of Lake Kalamazoo, The Hotel Saugatuck is a quiet place to rest and unwind. The hotel portion of this luxe bed and breakfast was built in 1865 as a lumber mill. The property has since added duplex cottages, upscale amenities like hydrotherapy tubs, and gourmet in-room breakfasts and desserts you can enjoy in front of a crackling fire. You can also book an in-room massage for maximum relaxation.

The Caramel Apple Getaway takes that in-room service to the next level. The property will pay for up to 10 pounds of the apples you pick at nearby Crane Orchards.  Don’t forget to explore the 20-acre corn maze and try an apple cider donut while you’re there. Once you’ve picked your apples, the hotel will bring the hot caramel and all the fixings to your room, so you can enjoy a caramel apple fondue and decorate your apples. The package is available through late October 2019.

A city break in Chicago, Illinois

For a classic city getaway in one of the most storied properties in Chicago, check out InterContinental Chicago Magnificent Mile Hotel. Constructed as an ultra-exclusive men’s club 1929, the elegant 42-story property houses the oldest pool in the city (complete with a hand-carved Neptune fountain hand-painted tiles and towering marble columns), and an interior overflowing with gold leaf moldings and hand-painted murals.

The Best of Chicago Package gives you a head start on your sightseeing. It includes accommodations and a pair of tickets to one of six of Chicago’s coolest attractions. Choose from VIP Passes to the Shedd Aquarium, All Access Admission to the Field Museum or VIP Tickets to the Art Institute of Chicago. Or get admission to The Ledge at Skydeck Chicago, General Admission to the Museum of Science and Industry or passes to the Chicago Children’s Museum and Navy Pier Ferris Wheel. Additional tickets are available for purchase at the front desk.

When you’re settled in for the night, you can check out the gorgeous skyline views while eating the complimentary skyline truffles. The Best of Chicago package is available this fall and must be booked three days in advance.

What about you? What’s your favorite fall getaway in the Midwest? Which one of these trips seem like the most fun and why? What are your favorite fall activities? Have you stayed at any of these properties? What did you think?

This post contains affiliate links. That means I may receive a small commission if you book a stay after clicking on a link I include here. Thanks for helping me fund some of my own fall travel!

You won’t miss a single post when you subscribe to Prairie Style File. Just look for the “Follow Prairie Style File” sign-up on the right side of the page. Or follow my adventures across the Midwest, the prairie provinces of Canada and around the world on Facebook, Twitter and Instagram.

Tag your pics and travel tips #PrairiePeople and #PrairiePlaces on Facebook, Twitter, Instagram and Pinterest. You could inspire an upcoming post on Prairie Style File. Prairie Style File is curated by Alicia Underlee Nelson. All rights reserved.

11 views0 comments


bottom of page