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The Ultimate Romantic Midwest Getaways

May 2025
SMTWTFS
May 2025
SMTWTFS

Planning the ultimate romantic Midwest getaways starts with choosing the right destination. Love can thrive anywhere, but the right setting can transform a simple getaway into something unforgettable. This region is brimming with charming small towns, stunning landscapes, and vibrant cities that cater to every couple’s idea of romance. It matters less what you do during your getaway and more that you choose to spend the time together. The Midwest is a fantastic place to enjoy activities that bring you closer together. 

Escape to Door County, Wisconsin, where waterfront sunsets and quaint coastal vibes set the tone for a memorable retreat. Or, explore the scenic beauty of the Great River Road, where adventures like hiking and snowshoeing pair perfectly with cozy evenings by the fire. For those seeking a cultural twist, cities like Chicago and Minneapolis/St. Paul offer world-class dining, live music, and vibrant arts scenes. Spend a weekend sampling wines in the vineyards of Wisconsin or Minnesota, take a romantic stroll through Minnesota’s North Shore in the fall, or go antiquing in Illinois. If you’re looking for something more adventurous, hit the slopes at ski resorts in Wisconsin or explore hidden hiking trails in Iowa.

Each season offers its own unique opportunities for couples to reconnect, relax, and create lasting memories. Of course, no romantic getaway is complete without the perfect place to stay. The Midwest Association of Independent Inns offers a collection of intimate properties designed to make your trip extra special. Imagine waking up in a historic bed and breakfast or enjoying the elegance of a boutique Inn. Consider a luxury cabin or an inviting retreat in the rural countryside for something more private. Whatever your preference, these properties combine charm and hospitality to create the ideal backdrop for unforgettable Romantic Midwest Getaways. 

This Valentine’s Day (and beyond), you can choose from the most elevated, personalized, and romantic places to stay in the Midwest. Spoil yourselves with a luxurious weekend, and let our member properties treat you to the ultimate getaway. Book your romantic Midwest getaways today! 

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Galena, Illinois is one of the most romantic Midwest getaways

10 Fantastic Destinations for Romantic Midwest Getaways

Though it’s true that just about any destination can be considered an excellent spot for romantic Midwest getaways so long as you’re together, there are a few fabulous destinations across the Midwest that have earned a solid reputation for romance. Whether you’re choosing to center your getaway in one of the best Midwest cities or would prefer an off-the-beaten-path adventure, you’ll no doubt find a fantastic destination with exceptional accommodations when you choose to stay at one of the incredible Inns, Bed and Breakfasts, or Cabins of the Midwest Association of Independent Inns. 

Wherever you go across the Midwest this year, you’ll find plenty of immersive opportunities to experience the region’s rich cultural heritage, warm hospitality, and countless attractions. If you’re looking for the best romantic Midwest getaways for couples, you’re in the right spot! We’ve curated a fantastic list of some of the most romantic destinations for couples in Wisconsin, Illinois, Iowa, Minnesota, and Nebraska – states that all have an exceptional range of accommodations and romantic places to stay. 

  1. For historic, small-town charm that exudes romance around every street corner, head to Galena, Illinois – easily one of the most romantic getaways in Illinois. Galena, tucked into the rolling hills of western Illinois, is a charming town perfect for a romantic getaway. From skiing at Chestnut Mountain with stunning views of the Mississippi River to sampling wines at local vineyards, there’s something for every couple to enjoy. 
  2. If you’re looking for a big-city vibe that’s as charming as it is romantic, head to Milwaukee, Wisconsin. Milwaukee offers a mix of quirky charm and vibrant activities, making it an ideal city for couples to explore together. Stroll through the lively Milwaukee Public Market for local eats or take in scenic views along the Riverwalk. Don’t miss exploring the Historic Third Ward, visiting unique museums, or catching a live performance at venues like the Fiserv Forum.
  3. Cedarburg, Wisconsin, just a short drive from Milwaukee, is a top pick for couples looking for romantic getaways in Wisconsin. This charming town invites visitors to explore its historic streets, browse unique local shops, and enjoy wine tasting at its celebrated wineries. With its welcoming inns and vibrant downtown, Cedarburg is an ideal spot for a relaxing and memorable weekend together.
  4. If breathtaking natural scenery is in your plans for your romantic Midwest getaways, don’t miss Sturgeon Bay in Wisconsin’s Door County. Explore the town’s vibrant art galleries, enjoy waterfront dining with stunning views of Lake Michigan, or take a leisurely walk to one of its iconic lighthouses. Whether visiting in the fall for colorful foliage or in winter for peaceful snowy trails, Sturgeon Bay is a perfect spot for reconnecting and making lasting memories.
  5. For an unbeatable riverside getaway, head to the charming Minnesota town of Stillwater. Couples love its historic downtown filled with unique shops, inviting restaurants, and views of the scenic St. Croix River. A leisurely walk by the water or a cozy evening exploring the town’s vibrant atmosphere makes for an unforgettable experience and is undoubtedly one of the most romantic Midwest getaways. 
  6. If a rural adventure in the heart of the Midwest’s Amish country sounds appealing, head to the charming town of Lanesboro in southern Minnesota. Lanesboro, known as Minnesota’s “Bed and Breakfast Capital,” is a favorite for couples looking to escape and reconnect. The Root River Trail offers endless opportunities for biking, hiking, or simply soaking in the beauty of Bluff Country. With its charming atmosphere and glimpses into Amish culture, Lanesboro creates the perfect setting for memorable romantic Midwest getaways. 
  7. If you’re looking for a scenic getaway on the Mississippi River this winter, consider the charming riverside town of Clinton, Iowa. Couples can enjoy stunning sunsets over the Mississippi River, explore the historic architecture of the Lyons District, or take in a show at the elegant Clinton Area Showboat Theatre. With its inviting local restaurants and scenic parks, Clinton provides the perfect backdrop for a memorable escape.
  8. For a charming and romantic destination that packs an abundance of local culture, head to Pella. With its rich Dutch heritage, Pella is the perfect setting for romantic getaways in Iowa. Stroll through charming streets lined with European-inspired architecture, enjoy the warm glow of festive winter lights, and indulge in fresh pastries from local bakeries. From exploring the iconic Vermeer Windmill to taking in the beauty of Lake Red Rock, Pella offers couples a delightful mix of culture, flavor, and scenic charm.
  9. Treat your partner to a romantic escape in the charming town of Spring Green, Wisconsin. Famous for its artistic flair and breathtaking surroundings, Spring Green combines creativity with natural beauty. Don’t miss iconic attractions like Frank Lloyd Wright’s Taliesin or the whimsical House on the Rock, which are perfect for creating unforgettable memories together.
  10. Finally, for another big-city adventure that also happens to be one of the best romantic Midwest getaways, don’t miss time in the Twin Cities of Minneapolis and St. Paul. Minneapolis and St. Paul perfectly blend city excitement and romantic charm. From strolling along the Mississippi River at sunset to dining at award-winning restaurants and exploring world-class art museums, the Twin Cities provide endless opportunities for connection. Whether catching a live show at the Guthrie Theater or relaxing in a cozy boutique hotel, this vibrant metro area sets the stage for unforgettable moments.
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same sex female couple making hearts with their hands during their romantic Midwest getaways

The Most Romantic Places to Stay in the Midwest

The Midwest is brimming with destinations perfect for a romantic getaway, offering everything from charming small towns to vibrant cities. Whether you’re planning a cozy weekend escape or celebrating a special occasion, the region’s welcoming spirit and understated elegance set the stage for an unforgettable trip. And when it comes to romantic places to stay in the Midwest, you’ll find exceptional options that go far beyond the ordinary.

The Midwest Association of Independent Inns showcases some of the most enchanting accommodations across states like Wisconsin, Minnesota, Iowa, Illinois, and Nebraska. From intimate Bed and Breakfasts to boutique inns and rustic cabins, these properties cater to couples seeking a stay that’s both unique and deeply personal. Each offers a blend of thoughtful details and warm hospitality, making your couple’s getaway feel truly special.

Imagine waking up in a room filled with character, where every detail reflects the romantic charm of the destination. Enjoy a leisurely breakfast prepared with care, featuring local ingredients and seasonal flavors. Many of these properties also provide spaces perfect for quiet moments together—think cozy fireplaces, private patios, or even luxurious spa tubs. These romantic touches create an atmosphere where you can relax, reconnect, and savor every moment.

Each inn is a reflection of its surroundings, with hosts who know the area intimately and can guide you to the best experiences. Whether it’s a scenic drive, a tucked-away restaurant, or a secret hiking spot, they’ll ensure your trip is as memorable as it is meaningful. For couples drawn to history, many of these properties are housed in historic buildings with captivating stories, offering an added layer of depth to your stay.

Make this the year you discover the heart of the Midwest with someone special. Explore romantic places to stay in the Midwest and create memories you’ll treasure forever. Your perfect romantic Midwest getaways await. Book your stay with one of these exceptional Midwest lodging properties today!

Lodging Properties near topics in our blog

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The Three Elizabeths Guest House

  • 101 West Main Street
    Elizabeth, Illinois 61028
  • 815-990-8618
  • Email Us
Located 15 minutes East of Galena, accommodations include three Guest Rooms, classically styled, each with their own private bath. Reasonable rates and a welcoming front porch entice visitors.
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The Muse Gallery Guesthouse

  • 602 East Lincoln Avenue
    Milwaukee, Wisconsin 53207
  • 414-745-7735
  • Email Us
The Muse Gallery Guesthouse is an art gallery inn in the heart of Bay View – Milwaukee’s, trendiest neighborhood. It is conveniently located near the Lake Express ferry port, airport, and downtown.
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Garden Gate Bed & Breakfast

  • 434 North 3rd Avenue
    Sturgeon Bay, Wisconsin 54235
  • 920-217-3093
  • Email Us
A premier Victorian bed and breakfast, the Garden Gate welcomes you with its friendly hospitality and elegant breakfast located in Beautiful Door County, Wisconsin.
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Hawk Valley Retreat & Cottages

  • 2752 West Cording Road
    Galena, Illinois 61036
  • 815-777-4100
  • Email Us
You are invited to relax, restore, and explore at our Galena Illinois Bed and Breakfast, a nature lover’s destination. We are located just 8 miles east of downtown Galena, IL.
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Hidden Serenity B&B Getaway & Spa

  • 1876 Shalom Drive
    West Bend, Wisconsin 53090
  • 262-623-0148
  • Email Us
Indulge in our all-inclusive spa, complete with jetted tub, steam room and sauna set in a romantic ambiance enveloped by 40 acres of lush forest. Get a massage, play pickle ball or hike our trails.
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Como Lake Bed and Breakfast

  • 1205 West Como Boulevard
    Saint Paul, Minnesota 55103
  • 651-399-4111
  • Email Us
Classic Craftsman style Inn overlooking St Paul’s Como Lake and adjacent to the regional gem, Como Park.
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Hotel Galena

  • 324 Spring Street
    Galena, Illinois 61036
  • 815-777-0123
  • Email Us
Located in historic downtown Galena, Hotel Galena offers a fabulous experience at an exceptional price. Boasting a 5* Google rating, it’s perfect for couples, families, groups, or solo travelers.
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Scofield House B&B

  • 908 Michigan Street
    Sturgeon Bay, Wisconsin 54235
  • 920-743-7727
  • Email Us
Victorian elegance and modern amenities within walking distance to shops and restaurants in downtown Sturgeon Bay! Enjoy a full breakfast and explore Door County.
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The Foxglove Inn

  • 344 North 3rd Avenue
    Sturgeon Bay, Wisconsin 54235
  • 920-746-9192
  • Email Us
Built in 1877, the Foxglove Inn is a charming, luxurious grand Victorian home where guest receive homemade chef-inspired breakfasts delivered to your door, walking distance to downtown Sturgeon Bay.
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Afton House Inn

  • 3291 Saint Croix Trail South
    Afton, Minnesota 55001
  • 651-436-8883
  • Email Us
Historic Afton House Inn (24 rooms) Most rooms include Jacuzzi for 2, Gas or Electric Fireplaces, Balconies & Walkout Patios. Some rooms overlook Marina. Breakfast Included. 3 Restaurants on site.
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Sheridan’s Bed & Breakfast

  • 5133 South Lake Drive
    Cudahy, Wisconsin 53110
  • 414-747-9810
  • Email Us
This historic 1920’s building has been beautifully renovated and offers 8 private guest rooms, each named and styled after wine making regions.
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Cloran Mansion Bed & Breakfast

  • 1237 Franklin Street
    Galena, Illinois 61036
  • 815-777-0583
  • Email Us
Guests to the Cloran will find modern comfort surrounded by historic charm. Treat yourself to 21st-century amenities certain to pamper while taking in the beauty of 1800s Italianate architecture!
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Andor Wenneson, now The Wen Inn

  • 425 Prospect Street
    Peterson, Minnesota 55962
  • (507) 577-9691
  • Email Us
Constructed over a century ago, the Wen holds a unique charm that is perfectly molded within its extended history. Retaining original antiques from the 1900’s, you will be transported back in time.
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Fisher House Bed & Breakfast

  • 407 5th Avenue South
    Clinton, Iowa 52732
  • 563-249-8948
  • Email Us
A completely remodeled Queen Anne Victorian home that features 4 unique bedrooms each with a private bathroom. There are 2 rooms with queen size beds and 2 rooms with king size beds.
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White Lace Inn

  • 16 North 5th Avenue
    Sturgeon Bay, Wisconsin 54235
  • 920-743-1105
  • Email Us
The White Lace Inn has 18 inviting guest rooms in four turn-of-the-century neighboring homes furnished in antiques, queen or king size Victorian beds, oversize whirlpools & fireplaces.
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Historic District Bed and Breakfast

  • 483 Ashland Avenue
    Saint Paul, Minnesota 55102
  • 763-360-3717
  • Email Us
A high value boutique inn with a gourmet breakfast and personal service in a unique and historic neighborhood. Close to museums, concert venues, small business owned restaurants and bars.
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Brisbane House

  • 7050 Reimann Road
    Arena, Wisconsin 53503
  • 608-576-6696
  • Email Us
Celebrate friends, family, and your story. Beautifully restored for you to fully experience. A rare treat, the charming Brisbane House is on the State and National Registers of Historic Places.
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Silver Star Bed and Breakfast Inn

  • 3852 Limmex Hill Road
    Spring Green, Wisconsin 53588
  • 608-935-7297
  • Email Us
Near Spring Green, we are a secluded 10 room log inn on 70 rural acres in the Driftless area of Wisconsin. We provide personal B&B service, with hotel quality beds, hearty breakfasts & fresh cookies.
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The Midwest Association of Independent Inns was formed to help the discerning traveler find the best Bed and Breakfasts, Inns and Boutique Hotels. Our member properties are located throughout the Midwest with plans to welcome properties from all 13 Midwest states.

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