319 Meeker St. Galena, IL 61036

815-777-3000

RESERVATIONS

Downtown Galena

Looking For the Best Weekend Getaway Near Chicago?

The Best Weekend Getaway Near Chicago is our Galena IL Bed and BreakfastIf you’re looking for the best weekend getaway near Chicago, you’ve come to the right place!  Galena has long been considered to be a top getaway destination for those in Chicago and other major cities in the Midwest, including Milwaukee, Madison, and even Minneapolis/St. Paul.  From Chicago, Galena is considered to only be a one-tank getaway, as it takes just under 3 hours to get here.

If you haven’t yet made the trek from Chicago to Galena, you’re missing out on a truly extraordinary little town, and, as it happens, the Best Galena IL Bed and Breakfast. With plenty of awards and accolades and an incredible number of 5-star reviews standing behind our name, you’ll soon see why the Jail Hill Inn is the best weekend getaway near Chicago. Book a room, and come explore this romantic piece of Illinois with us! Continue reading

10 Things You Simply Must do in Galena This Winter

10 Things to do in Galena This WinterHave you ever visited Galena during the winter? It’s a wonderful place to visit, even when there’s snow on the ground!  There are plenty of delightful things to do this winter, and we have a great guide for you. Head out on a cross country skiing adventure, explore our vibrant and historic downtown, or sit back and savor the luxurious accommodations found at our Galena Bed and Breakfast.

Galena has long-been a popular getaway destination for those living in or around the Chicago area, and these winter months should be no different. Even if you don’t love spending time outside during the winter, the chance to stay at our romantic Inn is more than worth the time it takes to get here. Your day will start with a delicious breakfast, but that definitely isn’t the end of our award-winning hospitality.  In the afternoon, join us for a delicious wine and cheese hour, along with some delicious fresh cookies, hot from the oven. Come see it for yourself, and book a room at our Galena Bed and Breakfast today. Continue reading

10 Reasons Why We’re the Best Galena Bed and Breakfast

Stay at the Best Galena Bed and Breakfast this WinterIt’s bold to assert that we are the Best Bed and Breakfast in Galena, but it’s a statement we can firmly stand behind.  In fact, not only is Jail Hill Inn the best Galena Bed and Breakfast, but we’re the best Bed and Breakfast in the entire country, according to TripAdvisor. After 4 incredible years in business, we’re thrilled to have seen the successes we’ve had in 2019, and are looking forward to an incredible 2020 with our guests, friends, and family.

If you’re looking for a beautiful and fun getaway destination this winter, consider staying at the Jail Hill Inn so you can see what all the hype is about for yourself. Book your room at Galena’s Best Bed and Breakfast today!

10 Reasons to Stay at our Galena Bed and Breakfast

We know that an essential part of a great getaway is where you stay. Where you stay and the experience you have there can often make or break the trip and how you remember it. To that end, we take special care to treat you to a truly luxurious stay while you’re at our Galena Bed and Breakfast.

Best Galena Bed and BreakfastBeyond just being able to say you visited the country’s #1 rated Inn, here are 10 more reasons to come stay at our Galena Bed and Breakfast in 2020:

  1. We offer 6 distinctly decorated guest suites, each thoughtfully designed with you in mind. Each of our three-room suites encompasses an impressive 800-square foot space where every detail is attended to with genuine care to ensure our guests experience a getaway that far exceeds their expectations.
  2. We are within easy walking distance of everything you could possibly want to do in downtown Galena, including the finest restaurants, entertainment, shopping, and more!
  3. We put luxury touches into everything we do, including our amenities. All the “standard” amenities are far beyond ordinary, and they include things like plush spa robes, Aveda personal care products, bath salts, Frette bath towels, Kohler bubble massage tubs or steam showers, and so much more.
  4. We also offer a variety of value-added amenities and services, including in-room massages, a daily wine and cheese reception, decadent, homemade cookies each evening (requests accepted!), a Tesla charging station, and so much more.
  5. Each of our guest rooms has the latest and greatest in technology, including a Bluetooth sound system that you can customize however you see fit and a Samsung Smart Tv.
  6. Each night of your stay is followed by a delicious, gourmet breakfast made right here at the Inn. We utilize fresh and local products whenever possible, including our own produce from our country gardens. Our breakfasts are considered by many to be the absolute best in town, and the only way to savor our culinary delights is by staying with us!
  7. We’re constantly redecorating, updating, and fixing the Inn to keep it looking brand new and impeccable for you!  For example, this year we recarpeted all of the suites, we added stairs and a deck to our backyard, and we just recently finished repainting some bathrooms.
  8. We offer Rewards!  JHI offers the Repeat Offender Program as a way of rewarding your loyalty. Visit us at least 6 times and stay in each of our six distinctive and luxurious suites, and you’ll earn a free two night midweek stay in a suite of choice.
  9. We care about our community, and give back to it whenever we can!  Our Posting Bail Program specifically gives part of our proceeds throughout the year back to three local non-profits whom we value greatly.
  10. We are a member of Select Registry, which is a diverse collection of independent, boutique properties that deliver a level of personalized service unheard of at hotel chains, and something you will only find at select few properties like ours.

If those 10 reasons aren’t enough of a reason for you to book your Galena getaway now, perhaps this will be:  We have 421 unique reviews on TripAdvisor, and each and every one of them are 5-star reviews.  98% of our 150 reviews on Google are also 5-star reviews (the other 2% are 4-star reviews). We think that speaks volumes about what you can expect when you stay at our Galena Bed and Breakfast.

Do You Need More Reasons to Visit Galena?

Stay at the Best Galena Bed and Breakfast Having the opportunity to stay at the Best Galena Bed and Breakfast is certainly a good enough reason to make the journey here.  But if you’re looking for more, you’re in luck!  For such a small town, Galena hosts an incredible variety of exciting weekend events and activities throughout the year, many of which have proven extremely popular.  Your time here can be spent dining out, sipping on wine, shopping, biking, hiking, skiing, kayaking or paddleboarding, driving through the beautiful countryside, laughing with friends, or just relaxing in luxury at our Galena Bed and Breakfast. Whatever it is you want to do, rest assured you’ll find it here!

As we’ve become accustomed to saying over the past year, if there’s something you really want to see or do in Galena, it’s best to book early, and book often.  What are you waiting for? Come see the Midwest’s most charming town, and stay at Galena’s Best Bed and Breakfast.  Book your rooms at Jail Hill Inn today!

10 Instagram Photos to Take of Galena This Fall

Instagram Worthy Photos to Take When you Visit our Bed and Breakfast in GalenaThough many of us may not want to admit it, we love to capure picture-perfect moments of our vacations to share on Instagram. It helps when you have an exceptionally beautiful place to photograph! If you’ve ever visited Galena in the fall, then you know just how extraordinarily beautiful this historic little town is. If this will be your first time, you’re in for a treat. The hillsides around Galena light up in their fiery shades of fall each September and October, making for a breathtaking display that must be experienced to be believed.  Galena, located within easy driving distance from Chicago, Minneapolis, Des Moines, and St. Louis, is the perfect getaway destination this fall. Between hiking through the beautiful fall colors and soaking up the small-town charm of downtown Galena, there are a number of Instagram worthy destinations to show off during your stay in picturesque Galena.  Book your room at the Jail Hill Inn, and enjoy another spectacular fall at the country’s #1-rated Bed and Breakfast. Continue reading

Browse Main Street in Downtown Galena

Main Street in Downtown Galena, IllinoisThough Galena is a lively four-season destination, there’s no doubt that things are starting to pick up here in Galena, as we head into the final stretch of spring and onto summer.  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.  It’s no wonder Galena has consistently been ranked as a top getaway destination. 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

Hit the Trails Around Galena

Hiking and Biking Trails in GalenaAs we officially sail into summer in just a few days, it’s time to start making plans to enjoy the warm summer sun.  There’s no better place to do this than the charming, historic town of Galena.  Our historic Main Street is nestled along the scenic Galena River, and surrounded by the rolling hills pervasive in this region of Illinois.  Plan a getaway to our luxury Bed and Breakfast, and you’ll be situated just steps from all downtown Galena has to offer.  From the moment you step through our doors at the Jail Hill Inn, it’s time to embrace a simpler time.  The picturesque countryside will beckon you into the great outdoors.  Galena is home to many great hiking and biking trails just waiting to be discovered.  Book your room at our Galena Bed and Breakfast today. 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

A Magical Winter Getaway in Galena

Winter Getaway in GalenaCountless couples over the years have been witness to the magical ambiance of Galena in the Winter time.  There is truly something special about it here. Glistening white snow covers the ground, old-world architecture stands stately, couples stroll hand and hand through our picturesque winter wonderland, and cozy fires are ablaze in businesses and homes around town.  Guests from all over come for skiing, snowboarding, sleigh rides, candlelit hikes, and romantic dinners.  What’s more, Galena offers an incredible range of shops, art galleries, spas, and live entertainment to fill your days and nights.  The offseason is special, and Valentine’s Day is coming up just around the corner.  The Jail Hill Inn still has some availability for the surrounding weekends, but we will soon sell out.  Book your getaway now, and see why we say you’ll always want to return, and you’ll never want to leave. 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.