319 Meeker St. Galena, IL 61036

815-777-3000

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Galena Bed and Breakfast

Downtown Galena is the #1 Place for Holiday Shopping

holiday shopping in downtown galena near our Bed and Breakfast in IllinoisNovember is officially here, and that means many of us around the country are gearing up for the holiday season ahead.  If you’re coming to Galena sometime in the next couple of months, you’ll find that downtown Galena is the perfect place to unwrap a little holiday magic and get a jump start on your holiday shopping. Main Street in Galena is lined with more than 100 unique and independently owned boutiques and is the perfect place to find fantastic gifts for everyone on your list.

And, of course, while you’re here, let us take care of you at the #1 Rated Galena Bed and Breakfast, Jail Hill Inn.  From the moment you arrive at our doorstep, you’ll see and feel the difference!  We offer luxurious guest rooms and amenities that go far beyond what you’ll find at other properties and hotel chains.  Every detail of your stay, from start to finish, is thoughtfully planned out to ensure maximum enjoyment.  Plus, we’ll soon be decorated for the holidays and ready to celebrate this festive season with you!

Holiday shopping in downtown Galena is something we look forward to every year.  Come join us this season, and help up support all of these incredible business owners that make Galena the wonderful getaway destination that it is! Book your room at our Galena Bed and Breakfast today. 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

What’s New at Galena Restaurants This Fall

5 of our Favorite Galena Bed and Breakfasts to Try This Winter

We’re avid supporters of local businesses, including our incredible slate of Galena IL Restaurants.  These small businesses are the backbone of our local economy and support those of us in the tourism sector by providing exceptional things to do and other amenities for our guests.  As a relatively small town, you might not expect these restaurants in Galena to pack much of a punch, but we think you’ll be pleasantly surprised!

Galena IL Restaurants are as diverse and interesting as the rest of the town.  Right now, most of the dining in downtown Galena is taking place outside on the town’s newly-created Pedestrian-friendly zone. But there are also plenty of takeout options from local restaurants as well, which you are more than welcome to bring back to our Galena Bed and Breakfast, where you enjoy your meal in the privacy of your own room or in one of our many common areas, both indoors and out.

This winter, we hope you’ll consider getting out of the city for a few days, where you can sit back, relax, and enjoy the ambiance of beautiful small-town America. Book your room at the country’s #1 Bed and Breakfast, the Jail Hill Inn, today!

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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

10 Things to do at Apple River Canyon State Park This Fall

Things to do at Apple River Canyon State Park Near GalenaThere really are a lot of things to do in Galena this fall!  It’s hard to choose a favorite, but enjoying the splendor of fall in the great outdoors is an absolute must. One of our favorite places to get outside in these crisp fall months is the Apple River Canyon State Park.  It’s actually beautiful any time of the year, but the juxtaposition of fall colors against the park’s landscape in the fall really is breathtaking. Apple River Canyon State Park encompasses an area of just under 300 acres here in this scenic portion of Illinois, and it is the perfect place for nature loves to get outside and away from the crowds of downtown Galena.

With so many great things to do in Galena throughout the year, it’s a wonderful place to return to time and time again.  And, when you do, there’s one Bed and Breakfast that stands out amongst the rest; Jail Hill Inn.  Jail Hill Inn, which was rated the #1 Bed and Breakfast in the country in 2019 and #3 in 2020, truly is the best Bed and Breakfast in Galena. Our Inn offers unparalleled service with luxury touches throughout, and we’re within walking distance to downtown Galena’s shops, restaurants, and attractions.  Staying here will certainly lend an air of unforgettable elegance to your Galena getaway.  Book your room at our Galena Bed and Breakfast today! Continue reading

The 10 BEST Things to do in Galena This Fall

10 of the BEST Things to do in Galena This Fall Near our Bed and BreakfastThings often look different in Galena from year to year, with new attractions, events, shops, restaurants, and other things added to our list each year. This year, mostly thanks to the COVID-19 Pandemic, things are definitely different in Galena.  Even so, it’s still one of the best weekend getaways from Chicago, and there are plenty of wonderful things to do in Galena this fall.  While many of our favorite fall events have been canceled in 2020, we have some ideas to ensure you have a fun and memorable getaway.

At the heart of your stay in Galena, you’ll still find the same exceptional accommodations offered by Jail Hill Inn, Galena’s #1 rated Bed and Breakfast. The experience of staying with us hasn’t changed too much, but there are a couple of notable adjustments. Breakfast does look a little different, in that we’re offering two choices: You can still enjoy us in the socially-distanced dining room downstairs, or you can request breakfast be brought directly to your suite.  And, in the afternoon, rather than hosting an afternoon wine and cheese reception, we’re delivering hand-crafted trays with your own personalized selection of wine and a delicious assortment of charcuterie, appetizers, and cookies for you to munch on at your leisure.

One thing that hasn’t changed at Jail Hill Inn is our absolute dedication to hospitality, where every detail of your stay is carefully attended to.  This fall, come celebrate the changing of the seasons with us.  Discover new things to do in Galena this fall, and leave with unforgettable memories and plans to return again.  Book your room at our Bed and Breakfast in Galena today! Continue reading

Scenic Drives Around Galena, IL

Fall Scenic Drives Near our Galena Bed and BreakfastFall is a breathtakingly beautiful time of year to be in Galena.  One of our favorite ways to enjoy fall in Galena, IL is to take scenic drives, of which there are plenty near our Bed and Breakfast. The winding country roads are absolutely perfect for these scenic drives, too!  Fall’s seasonal display of color paints the hills around Galena, bringing this area to life in new and exciting ways.

Making yourself at home at our luxurious Galena Bed and Breakfast is the perfect recipe for a memorable and exciting vacation.  We take the meaning of hospitality to a new level, and, most importantly, are dedicated to keeping travelers safe during these unprecedented times. If you’ve never experienced fall in Galena before, this year provides you with the perfect opportunity.

Not only is it a beautiful place to relax and unwind, but it’s a safe and comfortable place to get away for that much-needed change of scenery.  Book your room at our Galena Bed and Breakfast today! 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

10 Delicious Tastings to Try in Downtown Galena

Tastings in Downtown Galena, ILDowntown Galena, IL holds so many wonderful shops, businesses, and restaurants, and is certainly much more than meets the eye. At first glance, downtown Galena might appear to be a sleepy downtown cloaked in historic buildings. And, while that’s true, which quaint town is absolutely packed with character and ineffable charms sitting just behind the historic facades.  We love walking up and down Main Street, exploring the many boutiques along the way. But what if we told you there was an even better way to enjoy downtown Galena?

Downtown Galena, IL is home to an incredible number of food purveyors, and is absolutely packed with flavor!  Tasting your way down Main Street has become one of our favorite activities, and certainly one of our favorite things to recommend to guests who stay at our Galena Bed and Breakfast. This summer, Main Street has turned into a pedestrian-only zone to help allow for air circulation and social distancing, and to ensure the safety of all who visit us in Galena.  Join us for some unique tastings along Main Street, and book your room at our #1 rated Galena Bed and Breakfast today! Continue reading

Make the Most of Your Visit to Galena This Summer

What to do in Galena IL This SummerThis summer, vacations and relaxing getaways are looking quite a bit different in most places around the country.  Even so, our Galena Bed and Breakfast is proving to be a wonderful place to relax, unwind, and enjoy the very best of this small town.  But when it comes to travel this summer, do you find yourself wondering what to do in Galena IL? The town of Galena has been working hard to put various protections and protocols in place to ensure the safety of visitors who choose to come here, while at the same time making it the same fun and romantic destination you’ve come to know and love.

Our Galena Bed and Breakfast has made many changes to our daily service as well, including changing up the way we serve breakfast and our afternoon happy hour.  We’ve been busy since reopening in June and have been receiving plenty of positive feedback from the guests who’ve stayed with us, both about how smoothly their experience with us went, and how much they enjoyed their time in the area as well.  As a small town, Galena is uniquely situated to be a great travel destination for people around the Midwest this summer.

There’s only one Bed and Breakfast that’s been named the #1 Bed and Breakfast in the country, and that’s Jail Hill Inn.  We’re booking up quickly this summer, so make your reservations to enjoy the best of Galena with us this summer! Continue reading

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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!