319 Meeker St. Galena, IL 61036

815-777-3000

RESERVATIONS

Galena Events

Plan Now to Visit our Galena Bed and Breakfast in 2019!

Book Early and Book Often for popular weekends and events at our Galena Bed and BreakfastIt’s hard to believe that not only is 2019 here, but that January is nearing an end. 2018 was a wonderful year of business for us at Jail Hill Inn, and was capped off earlier this month when TripAdvisor’s Traveler Choice Awards were announced.  Jail Hill Inn has been recognized as the winner in the Inns/B&B category of the 2019 TripAdvisor Travelers’ Choice®awards for Hotels, ranking #1 out of 25 in the United States, and #2 in the World! Travelers’ Choice award winners generally reflect remarkable service, value, and quality. In the 3 short years since opening our doors, we have been so honored by a number of designations. Our guests, family, and friends are the most critical part of this exciting award, as we would not be here without you. Thank you for your continued loyalty to Jail Hill Inn!  As we look forward to another successful year making connections with our guests in 2019, we urge you to plan your getaways to Galena well in advance. Book early, and book often! Continue reading

Galena Wine Country Getaway

Galene Wine Country GetawayAs we head into the brisk months of fall, we’re all looking for ways to getaway, relax, and unwind.  The fall months in Galena are packed with plenty of fun activities and events.  Whether it’s getting outside for a hike, shopping along Main Street, celebrating over a romantic dinner for two, or touring and tasting your way through Galena’s wine country, Galena truly is a town that has it all.  This November, join us for one of Galena’s most popular weekends, the 34th Annual Nouveau Weekend. There’s no better way to celebrate the harvest of the season and the delicious wines produced in our area.  You won’t find better accommodations than those at Jail Hill Inn, downtown Galena’s top-rated luxury Bed and Breakfast. Book your wine country getaway with us today! Continue reading

Holiday Events and Celebrations in Galena

2017 Holiday Events in GalenaGalena’s event calendar is often packed around the holidays, and this year it’s no different.  At Jail Hill Inn, we’re gearing up for another exciting and busy holiday season, and hope you find time in your busy schedule to come visit us.  Galena is truly a magical holiday destination that you must see at least once in your lifetime.

The first of many fantastic holiday events this year starts this upcoming weekend with Galena’s 33rd Annual Nouveau Wine Weekend.  The Nouveau Wine Weekend is a celebration of the year’s harvest, and features the release of Galena Cellar’s first bottled wine of the year.   Continue reading

Wine and Hot Air Balloons: Two Great Events in Galena

Summer Events in Galena, IllinoisAs we head into the warmer summer months, things are starting to heat up here in Galena–both literally and figuratively.  The summer months are packed with plenty of fun activities and events.  Whether it’s getting outside for a hike, paddling down the picturesque Galena River, shopping along Main Street, celebrating at festivals, or sampling delicious wines, Galena truly is a town that has it all.  This June you can soar to new heights in a hot air balloon, or stay on the ground and sample the finest food and wine around.  Whatever it is you want to do, you won’t find better accommodations than those at Jail Hill Inn, downtown Galena’s newest luxury Bed and Breakfast. Book your summer getaway with us today! Continue reading

Discover Wineries in Galena

Wineries GalenaGalena, a town put on the map because it was the home of President Ulysses S. Grant, is a wonderful getaway destination throughout the year. It’s picturesque and quiet streets are filled with quaint shops and boutiques, gourmet restaurants, spas, and wineries. Even better, all of this and more is easily attainable, as Galena is only a one-tank trip from many large Midwest cities.  Throughout the year, there are a variety of events that draw wine lovers to Galena, and numerous wine bars and wineries to keep the fun flowing throughout the remainder of the year.  Book your room at our newly renovated and historic Galena Bed and Breakfast, and sip your way through Galena’s best wines. Continue reading

Discover History in Galena

Galena History Galena is the perfect getaway destination for a variety of people in the midwest.  It’s just one tank of gas away from many of the midwest’s large urban areas, yet it feels distinctly different.  More than that, Galena is a fascinating destination with a distinctive history and an interesting variety of things to see and do.  Located in historic Jo Daviess County, Galena is the perfect place for history lovers to spend a few days.  There’s no better time to explore Galena than this spring during one of the biggest Civil War events, the annual US Grant Pilgrimage weekend.  Our historic Inn, formerly the county jail, has recently been renovated into a modern and luxurious Bed and Breakfast, making it the perfect place to end your days in Galena.  Book your room with us today so you can getaway to Galena this spring. Continue reading

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Jail Hill Inn Bed and Breakfast in Galena Wins Top TripAdvisor Award

Jail Hill Inn has been named the #1 Bed and Breakfast in the United States and #2 in the world by TripAdvisor.