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The Best of the Best in Galena

The Most Romantic Getaway of the Year is Waiting

In the middle of a cold, dark winter, there’s something indulgent about planning a romantic getaway in Galena, IL, and giving you and your partner something special to look forward to. For the ultimate luxury couples getaway, turn to our Galena Bed and Breakfast. Not only have we been rated as the #1 Bed and Breakfast in the entire country (and #2 in the world!), but we are easily ranked as one of the most romantic getaways near Chicago.

Our incredible slate of 5-star reviews will tell you a lot about the experience and the many luxuries waiting for you here. We take the romance game seriously and love treating couples to memorable romantic getaways. With luxurious touches at every turn and the warmest, most welcoming and detail-oriented hospitality, it won’t take you long to feel perfectly at ease. There’s a reason we have earned AAA’s four-diamond designation!

Our Inn isn’t the only reason to plan a romantic getaway in Galena, IL, though. The town itself is a top tourism destination in the state and sets the perfect stage for a romantic escape. Galena’s historic downtown is filled with ample charm and character. It serves as an excellent place to unplug for a few days and slow down, enjoying uninterrupted time with your sweetheart. Whether you prefer to meander the streets of downtown Galena doing a little shopping, enjoy wine (and other) tastings, indulge in a massage or two, or breathe some fresh air on our local trails, you’ll find there’s no shortage of things to do in Galena. 

Of course, you may just find our guest rooms too relaxing to do much of anything – and that’s perfectly ok, too! Are you ready to experience the best romantic getaway near Chicago? Book your room at our top-rated Galena Bed and Breakfast today!

A cozy guest room at our Galena Bed and Breakfast - the best place for a romantic getaway in Galena IL

Plan the Perfect Romantic Getaway in Galena, IL

Though there may be many great choices for Galena lodging, nothing compares to Jail Hill Inn for a romantic getaway in Galena, IL. The Jail Hill Inn guest experience is far superior to what you’ll find at other local properties. We’re located just a few blocks from the shops, restaurants, and attractions in downtown Galena, yet are tucked away quietly on a hill overlooking the beautiful town and river valley below. 

Romance is at the heart of what we do here. We have thoughtfully curated every aspect of our guest experience, and this attention to detail makes our Inn the ultimate destination for a romantic getaway in Galena, IL. It’s an experience that starts the moment you check in to your guest room, too. Waiting for you will be a delicious box of custom chocolates made just for our Galena Bed and Breakfast and a chilled bottle of champagne. It’s a simple invitation to kick back, relax, and let the pampering begin. 

Setting the perfect stage for your romantic getaway are our guest rooms. We offer six luxurious suites, each featuring an impressive 800 square feet of space. Each guest room also features a sitting room, a kitchenette, a large spa-like bathroom, and a well-appointed bedroom, complete with a sumptuous king-sized bed. Aside from these basic luxuries, each guest room has a host of fabulous amenities to enjoy throughout your romantic getaway in Galena, IL. This includes things like dimmable lights, a customizable Bluetooth sound system, gas fireplaces, luxury Frette bathrobes, and just about everything else you need to enjoy an intimate weekend.

In the morning, join us in the dining room for our signature multi-course breakfast. It’s a true treat for the senses and will leave you feeling full and well cared for. In the afternoon, we invite you to enjoy some one-on-one time over our delicious wine & appetizer trays. We’ll bring it directly to your room for your own private happy hour, or you can take the tray and enjoy it in one of our common areas or outside spaces. 

If you’re looking for ways to add extra touches to your romantic getaway in Galena, IL, we’re here to help! We can help arrange in-room massages for one or both of you, and we’re always happy to make custom cakes, place fresh flowers in your room, or treat you to other romantic extras. Just let us know what you need, and we’ll help you make this getaway the most romantic and memorable romantic getaway in Galena, IL yet!

Gay couple enjoying drinks at a bar during their romantic getaway in Galena IL

Things to do During Your Couples Getaway

For many couples, the chance to stay at our award-winning Bed and Breakfast is the entire reason to plan a romantic getaway in Galena, IL. You may not want to leave the luxurious and pampered environs of Jail Hill Inn all that often – and we can hardly blame you! However, there is a charming and historic town just a few steps away that is more than worth exploring while you’re here.

However you like to spend your time, you’ll likely find plenty of fabulous things to do in Galena, IL. It’s beautiful here, and the historic charms of our streets, coupled with the friendly vibe of the town as a whole, make for a fantastic place to explore with your loved ones. From learning more about the town’s history to sampling wine at local wineries, there’s no shortage of great things to do in Galena. We’ve included some of our favorites below!

  1. Browsing the unique shops is one of the most popular things to do in downtown Galena, IL – and we don’t think you’ll be disappointed! There are more than 100 unique shops along Main Street to explore – you won’t find chain stores here!
  2. While shopping and exploring Main Street, don’t miss the opportunity to stop at a local winery for a tasting. Galena Cellars and Massbach Ridge Winery both have tasting rooms in downtown Galena. Other great places include Champagne on Main, Galena Brewing Company, and Blaum Bros Distilling. There are also a few vineyards in the surrounding area, including Fergedaboudit Winery and Rocky Waters Vineyard & Winery. Perhaps you want to consider Galena wine tours during your romantic getaway in Galena, IL?
  3. After all that shopping and wine tasting, you’ll need a great place to enjoy a romantic dinner. There are plenty of great Galena restaurants, including Fritz and Frites and Fried Green Tomatoes.
  4. If all you want to do is enjoy some beautiful scenery and conversation, we recommend taking a walk on the scenic Galena River Trail or one of the local nature preserves, such as Horseshoe Mound PreserveCasper Bluff Land and Water Preserve, and the Valley of Eden Bird Sanctuary.
  5. There’s also plenty of history to admire during your romantic getaway in Galena, IL. Consider touring one of our historic homes, such as the Belvedere Mansion or the U.S. Grant Home.
  6. In-room massages at our Galena Bed and Breakfast are the ultimate way to relax and unwind during your romantic getaway in Galena, IL, but if you’re looking for more spa treatments, we recommend the Stonedrift Spa at Eagle Ridge Resort.
  7. If you want to enjoy some of Galena’s nightlife, you have options! Head to a magic show at PT Murphy’s Magic Theatre, or grab a drink and enjoy the ambiance at Ms. Kitty’s Grape Escape or one of these other bars in Galena.

The only thing better than enjoying your time out and about in Galena is spending your romantic getaway in Galena, IL “inn” – and the only place worth doing that is our top-rated Galena Bed and Breakfast. Book your room today!

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Give The Gift of Jail Hill Inn This Christmas

Give your loved one a very special gift of a stay at Jail Hill Inn .  We offer gift certificates in many amounts.