319 Meeker St. Galena, IL 61036

815-777-3000

      Take Out Dining

RESERVATIONS

Galena Getaways

Are You Ready for Romantic Getaways in Galena IL?

A couple enjoying one of the most romantic getaways in Galena ILRomantic Getaways in Galena IL are a time-honored and special tradition and one we’re thrilled to be a part of here at our exceedingly romantic Galena Bed and Breakfast.  We don’t often give ourselves enough time to stop and smell the roses, so to speak, or more importantly to slow down, reconnect with those closest to us.  And, we must say, if there’s one lesson this pandemic has taught us, it’s to appreciate those few important humans who we’ve let into our lives and to nurture our connections.

We also know that one of the most important considerations to take into account when it comes to those romantic getaways in Galena IL is where you’re going to stay.  After all, your lodging accommodations are probably going to feature pretty prominently in any quality romantic getaway, where time alone is the time best spent. Our Galena Bed and Breakfast, rated the #1 Bed and Breakfast in the entire country in 2019, will happily help you set the perfect stage for these romantic getaways in Galena IL, too!  Our historic town has been a romantic escape for decades, after all.

Make sure to plan in enough “you” time, and enough “together” time is an important goal for many as we head further into 2021.  Why not take some time to start planning for those special moments right now?  The sweet little town of Galena IL will be right here waiting for you.  Book your romantic getaways at our Galena Bed and Breakfast today! Continue reading

Keep Your Resolutions at our Galena Bed and Breakfast!

Keep Your New Year's Resolutions at our #1-rated Galena Bed and BreakfastSometimes, it’s hard to get away and maintain your New Years Resolutions – especially at a place like our Galena Bed and Breakfast, where food is a central part of your stay!  It’s possible, though!

You’ll be served a breakfast every morning of your stay, but we’re happy to take requests and cater to your needs however possible. And, yes, we’ll also serve you a yummy tray of wine & snacks in the afternoon, which includes delicious charcuterie from our friends at Galena River Wine & Cheese. But that can be saved and eaten at your leisure throughout your stay – and maybe even turned into part of a light dinner!

Aside from the food, though, Galena is a great place to get away for some restorative “you” time. When it comes to getting some exercise, there’s plenty of that here, too!  We’d love to share Galena with you this winter AND help you stick to your New Year’s Resolutions, all while ensuring you’re being taken care of. There’s nothing quite like a getaway to Jail Hill Inn.  Book your getaway at our Galena Bed and Breakfast today! Continue reading

Is the Trip From Chicago to Galena Worth It?

Enjoy the Trip from Chicago to GalenaChicago is the nearest big city to Galena, and it only takes about 3 hours to get from Chicago to Galena.  Even so, you might be asking yourself if it’s worth making the trek from Chicago to Galena.  The answer to that is a resounding yes.  Of course, we think the opportunity to visit our Galena Bed and Breakfast is more than worth the effort, but visiting us is about so much more than the luxury accommodations you’ll find once you’re here; it’s also about this incredible, historic town that you’ll get to enjoy once here.

Galena is steeped in history, and it’s hard to get a sense of appreciation for it from afar. Dating back to its earliest days as a mining town, and later as the home of famed U.S President Ulysses S. Grant, there is much to see, do, and experience once here.  And, just as with any great road trip, the journey to get from Chicago to Galena is a beautiful one and is filled with plenty of small towns and picturesque vistas to enjoy along the way. What are you waiting for? Hop in the car, and head on out to Galena. Just make sure you have reservations at the incredible Jail Hill Inn before you go! Continue reading

How to Enjoy a Winter Getaway at our Galena Bed and Breakfast

The #1 BEST Galena Bed and Breakfast for your winter getawayIt’s not yet officially winter, but it’s getting chilly here in Galena and we’re preparing for the cozy and romantic season ahead.  Winter isn’t considered to be peak travel for many destinations around the country, Galena included.  But, there are plenty of reasons to plan a winter getaway – and when you do, there’s nowhere better to spend it than at our Galena Bed and Breakfast.

When it comes to things to do in Galena this winter, there’s more than enough to keep you busy, too.  Enjoy some socially distanced shopping or dining in downtown Galena, get out on the trails for a little winter hiking (or cross country skiing or snowshoeing), head to Chesnut Mountain for some skiing, or otherwise take the time to breathe the fresh air of Galena Country and sit back, relax, and let us take care of you!  Book your room at Jail Hill Inn, and get ready for the winter getaway of a lifetime.

Continue reading

Our Bed and Breakfast in Illinois is the Perfect Romantic Getaway

Romantic getaway at our Bed and Breakfast in IllinoisIf there’s one thing we do well at our Bed and Breakfast in Illinois, it’s cater to the romantics among us. In fact, romance is at the very heart of everything we do here. Whether it’s in the luxury touches of our spacious guest rooms, our delicious breakfast each morning of your stay, the luxury touches and amenities you’ll enjoy throughout your time with us, or just the private oasis that is our Bed and Breakfast in Illinois, you can be assured that this is one romantic getaway you won’t forget.

And that’s to say nothing about the romantically charming town of Galena itself!  This historic little town, just a few hours west of Chicago, seems as though it was built with romantic getaways in mind.  There are plenty of romantic things to do in Galena, including wine and other tastings, shopping, romantic dinners, picturesque strolls by the river, and so much more.

Come check out this sweet little town this winter, and give yourself the chance to get cozy at our romantic Bed and Breakfast in Illinois.  Book your getaway today! Continue reading

Discover the #1 Weekend Getaway in the Midwest

Our Galena Bed and Breakfast is the #1 Weekend Getaway in the MidwestAre you looking for somewhere romantic to curl up and get cozy this winter? Let us introduce you to our Galena Bed and Breakfast, considered by many to be the best weekend getaway in the Midwest. Our Bed and Breakfast is located in the charming, historic town of Galena, and only a few hours from major cities such as Chicago, Milwaukee, and Des Moines.

You might be asking what it is that makes Galena, and our Bed and Breakfast, in particular, such a delightful weekend getaway in the Midwest.  In part, it’s the many fun things to do in Galena, even in the chilly months of winter. Whether it’s getting outside for a little bit of adventure, strolling down Main Street and browsing Galena’s independent boutiques, enjoying a delicious glass of wine, beer, or spirits over laugh-filled conversations, or just enjoying the historic ambiance of this quaint town, you will be pleasantly surprised by all that Galena has to offer.

But your weekend getaway in the Midwest is about more than just the town of Galena. It’s also about the opportunity to stay in such a luxuriously elegant and historic building, and to let us take care of the details for a weekend while you do nothing but relax and enjoy the moment. When it comes to where to stay in Galena, there’s only one choice that brings you the romantic ambiance and touch of luxury that you’re looking for; Jail Hill Inn.

Our Galena Bed and Breakfast has been rated the #1 and #3 Bed and Breakfast in the country in 2019 and 2020, respectively. There are still some openings this winter, too, but you’ll need to act fast before those disappear.  Book your room at our Galena Bed and Breakfast today, and enjoy one incredible weekend getaway in the Midwest! Continue reading

We’re Still the Best Galena Bed and Breakfast

Stay at the Best Galena Bed and Breakfast This FallSince first opening our Galena Bed and Breakfast in 2015, Jail Hill Inn has enjoyed a number of awards and accolades, including our crowning achievement of being named the #1 Bed and Breakfast in the country, and the #2 Bed and Breakfast in the world, in 2019.  Those awards from TripAdvisor led us to our best year on record, and we entered 2020 with a great sense of hope and purpose.

While 2020 has certainly been a challenge, with the COVID-19 pandemic affecting not just our business, but those around the country, we’re still so thrilled to be open and busy welcoming guests this summer. This summer has brought many changes to Jail Hill Inn. We no longer host an afternoon wine and cheese hour, but instead deliver individual trays to your suites each afternoon, our breakfasts are now served at socially distanced tables (or to the privacy of your suite), and masks are required on our property.  Moreover, downtown Galena has, at least temporarily, closed down Main Street to vehicle traffic and has moved to dine outdoors onto the new Pedestrian Zone.

It’s been challenging but fun to rise to the occasion and pivot our business model to meet the demands of this pandemic, but it’s also been heart-warming to see how the entire town of Galena has come together and rallied to keep our thriving tourism destination a safe and welcoming space to getaway.  In midst of all of this, we’re also incredibly delighted to once again be named at the top of the list of the Best Bed and Breakfasts in the country.

For 2020, our Galena Bed and Breakfast ranks as the #3 B&B in the country, and #11 in the world.  It may not be #1 and #2, but we’re still near the top of the list, and that is something we’re incredibly grateful for! If you’re looking for a beautiful, safe, and welcoming getaway anytime in the near or distant future, we hope you’ll consider staying at Jail Hill Inn, so you can see what it’s like to stay at one of the best Inns in the world. Book your room at the Best Bed and Breakfast in Galena today! Continue reading

One of the Most Romantic Getaways in Illinois

Our Galena Bed and Breakfast is one of the most romantic getaways in IllinoisRomantic getaways are special. They offer you a time to slow down, reconnect, and focus on nothing but your relationship.  If we’ve learned nothing else during this COVID-19 pandemic, we’ve learned that being surrounded by and connected to our loved ones is the single most important thing in our life, so much more so than material things.

This summer, why not take time to fan those flames and reignite your passion for each other, all while enjoying one of the most romantic getaways in Illinois?  Galena, of course, has long been considered a charming destination in Illinois and is perfect for romantic getaways.

Beyond choosing a destination, you’ll want to choose accommodations that set the perfect stage for romance.  For that, turn to our luxurious Galena Bed and Breakfast.  We are the #1 rated Bed and Breakfast in the country, and the #2 Bed and Breakfast in the world, let alone the best in Galena, precisely because of the incredible hospitality we provide our guests.  From the moment you walk through our doors, you can expect an unparalleled lodging experience. Book your room today, and discover why our Galena Bed and Breakfast is one of the most romantic getaways in Illinois. Continue reading

Exciting Changes in Downtown Galena IL This Summer!

Explore Downtown GalenaThere have been some big changes to downtown Galena IL this summer in response to the COVID-19 pandemic, but we think they’ve been pretty great changes for the most part.  We recognize that travel feels a little different to all of us right now, but we hope you feel comforted knowing our entire town is working hard to create a safe and healthy environment for all who choose to visit!  You can find what we’re doing, specifically, on our website.

Travel studies released recently have shown that getaways that are closer to home and to smaller towns are considered to be one of the best options.  That is great news for Galena, as we’re located just under 3 hours outside of Chicago, and easily drivable from other major cities like Milwaukee, Minneapolis and St. Paul, and Des Moines. When you get to downtown Galena IL, you’ll notice a few things are different!

The town of Galena has decided to turn its Main Street, which is normally bustling with both cars and people, into a pedestrian-only zone.  It’s transformed our town and is allowing our local businesses to flourish once again.  That is, of course, provided you take the time to get here and join us!  With downtown Galena closed to traffic, staying nearby and within walking distance is more important than ever. Our Galena Bed and Breakfast is the perfect place to stay, as we’re located just off Galena’s Main Street, and within easy walking distance to everything downtown Galena IL has to offer.  Book your room at our Galena Bed and Breakfast today! Continue reading

One of the Most Romantic Getaways Near Chicago is Waiting for You

The most Romantic Getaways Near Chicago

Are you looking for one of the most romantic getaways near Chicago? Look no further; our Galena Bed and Breakfast has everything you want in a romantic escape and more. We know now is not the ideal time to be traveling, with the threat of COVID-19 still hanging in the air.  We’ve been shut down for several weeks per the order from the state of Illinois, and we will remain closed until it’s safe to open.

However, when we do get to the point of reopening, know that we’ll be here ready and waiting to welcome you back to our Galena Bed and Breakfast. At just under 3 hours from Chicago to Galena, our luxury Bed and Breakfast is the perfect place to rest, relax, and just get away. And, after weeks (or months!) of being socially isolated, we think getting away somewhere safe and secure is exactly what you’re going to be needing.

Clean, safe, and comfortable luxury.  That’s what awaits at our Galena Bed and Breakfast.  Give yourself permission to dream, and start planning your future trip to Jail Hill Inn todayContinue reading

Scroll to top

Now Offering Dinner from Brazen!

We’ve partnered with our friends at the sensational Brazen Open Kitchen in Dubuque to bring you a new Friday night food delivery option!