#1 BEST RATED Bed And Breakfast In Galena | Jail Hill Inn
Surpasses All Expectations! 
Absolutely Amazing In Everyway! 
Counting Down Til My Next Visit! 
- TripAdvisor 2021 Reviews

Welcome to Jail Hill Inn

Jail Hill Inn offers gracious lodging for a perfect getaway. A true gem, the inn delivers the ultimate in relaxation, luxury accommodations, and location. Tucked away, yet close enough to walk to Galena’s historic Main Street, the 135-year-old, 4-story brick building (which served as the county jail for nearly 100 years) has been lovingly transformed into Galena’s premier bed and breakfast inn by innkeeper Matthew Carroll.

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UNMATCHED LUXURY

Guest Suites

Each of the inn’s six uniquely appointed and luxurious suites boasts an impressive 800-square foot of space and a range of high-end amenities. Every detail of your stay is attended to with genuine care, ensuring Jail Hill Inn guests experience an unforgettable getaway in historic Galena, Illinois.

#1 on Trip Advisor

Our Inn

Jail Hill Inn is the #1-rated Bed and Breakfast in Galena. In 2019, TripAdvisor also named us as the #1-rated Bed and Breakfast in the Country, and #2 in the world. Housed in the historic 4-story brick building where the Jo Daviess County Jail once operated, the Jail Hill Inn offers its guests unmatched luxury and an up-close-and-personal glimpse into Galena’s storied history. 

UNIQUE GIFTS

Our Merchandise

We work hard to make sure every stay at Jail Hill Inn is special, and that includes offering customized, high-end amenities.  Many of the things you’ll enjoy throughout your stay, including our luxurious sheets and bathrobes, our custom roasted coffee and hand-made mugs, our annual holiday ornaments, and so much more are available for purchase in our online store. 

The Premier Galena Bed and Breakfast

Every Jail Hill Inn guest has access to enjoy the inn’s first-floor lounge area, a ground-level courtyard, and an expansive third-level deck, which overlooks the beautifully landscaped yard. All common areas are ideal for sipping a glass of wine, gathering with friends, enjoying a morning coffee and relaxing during the nightly wine and cheese reception.

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#1 Bed and Breakfast

In 2019, Jail Hill Inn was recognized as the #1 B&B/Inn in the USA (and #2 in the World) with a TripAdvisor Travelers’ Choice® award! In 2020 TripAdvisor ranked us at the #3 B&B in the United States. These incredible distinction reflects the impeccable hospitality and attention to detail every guest experiences at Jail Hill Inn.

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Member of Select Registry

Jail Hill Inn is a member of the prestigious Select Registry, the “gold standard” for inns and small properties. In 2018, the inn received the top score of nearly 300 inspected properties! An impressive 299 points out of a perfect 300.

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Business Leader

Jail Hill Inn is honored to be named the 2018 Business of the Year from the Galena Chamber of Commerce. Innkeeper Matthew Carroll’s collaborative spirit shows in his commitment to showcasing local talent and partner with area businesses.

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Sustanability

In an effort to offer guests a luxury stay without compromising the environment, Jail Hill Inn has taken steps to improve efficiencies and reduce waste. These sustainability actions have earned it a Green Lodging designation.

attention to detail

Amenities

Guests to Jail Hill Inn will find themselves surrounded by some of the most bespoke property & room amenities you can find. Each of our guest rooms features custom-made king-size beds with hypoallergenic pillows and fine Comphy Sheets.™  In each expansive private bathroom, guests will find Aveda personal care products and travel amenities. You will also find romantic gas fireplaces, KOHLER® BubbleMassage™ Air Bath with chromatherapy, and dual showerheads in showers.

CLASSIC & HISTORIC

Galena, Illinois

Galena is an incredible getaway destination, located just a few hours outside of major cities like Chicago and Milwaukee.  Once here, spend the time browsing the area’s top historic attractions, shop your way through Main Street’s boutiques, sip local wine, beer, and spirits, dine at our exquisite restaurants, and otherwise enjoy the chance to relax, unwind, and enjoy this stunningly beautiful town. 

BOOK DIRECT

Reservations

Jail Hill Inn has established itself as the premier Bed and Breakfast in Galena, IL.  Consequently, booking well in advance of your desired stay is highly recommended. We take reservations up to one year in advance, and our up-to-date availability is always shown directly on our website.  All bookings should be made on our website, as booking direct with us always ensures you the best rates possible!

The lastest from our Things To Do in Galena Blog

So what exactly happens when you purchase a Jail Hill Inn certificate from www.jailhillgalena.com @jailhillinn ?

A whole lot of of old fashioned magic to be honest!

My mom, Ginny, has hand written every Christmas Gift Certificate for JHI for the last 6 years and this year was no different of course! I spent the evening at mom and dad’s dining room table compiling, signing and boxing this first wave of gift certificates 2021! We are selling gift certificates in any $$$ in Dec and I’m being totally honest…who doesn’t want a JHI getaway for 2022!

Thank you all for this incredible love…it is genuinely felt! ❤️❤️❤️❤️
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As we head even further into the busy holiday season, don't forget to give yourself plenty of space to relax and unwind... and maybe pick up a cozy robe or two to snuggle into! ⁠

They're for sale (along with plenty of other goodies) in our online store, which is found at the Link in our Bio.⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #weekendgetaway #weekend #weekendvibes #weekendfun #wanderlust #getaway #boutiquehotel #weekendtrip #weekends #luxury #beautifuldestinations #adventure #bestvacations #summerfun #escape #galenacountry #galenaillinois #stayselect #selectregistry
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It's small business Saturday, which means it's time to head out and show those small Galena businesses just how much you love and appreciate them! We can't think of a better place to kick off your holiday shopping this year!⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #wanderlust #getaway #boutiquehotel #luxury #beautifuldestinations #adventure #bestvacations #escape #galenacountry #galenaillinois #stayselect #selectregistry #yummy #yum #nomnomnom #happyhour #shopsmall #shoplocal #smallbusiness #local
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Want to save on gift certificates to Jail Hill Inn! You only have a few days to take advantage of these great savings! Here's the special* for this year, valid Today through Monday, 11/29!⁠

Spend $100 - $200, get a $25 Midweek Bonus Certificate⁠

Spend $300-$400, get a $50 Midweek Bonus Certificate⁠

Spend $500 or more, get a $100- Midweek Bonus Certificate⁠

*Only one bonus gift certificate per guest. Double your purchase will not result in more bonus gift certificates. ⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #wanderlust #getaway #boutiquehotel #luxury #beautifuldestinations #adventure #bestvacations #escape #galenacountry #galenaillinois #stayselect #selectregistry #yummy #yum #nomnomnom #happyhour #gratitude #happythanksgiving #grateful
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Happy Thanksgiving! We hope you're all able to gather with friends and family this year. We're so grateful you're on this incredible journey with us, and look forward to many more years of stories and friendships!⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #wanderlust #getaway #boutiquehotel #luxury #beautifuldestinations #adventure #bestvacations #escape #galenacountry #galenaillinois #stayselect #selectregistry #yummy #yum #nomnomnom #happyhour #gratitude #happythanksgiving #grateful
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In the spirit of the food-focused holidays coming up - what's your favorite dish at your Thanksgiving table?⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #wanderlust #getaway #boutiquehotel #luxury #beautifuldestinations #adventure #bestvacations #escape #galenacountry #galenaillinois #stayselect #selectregistry #yummy #yum #nomnomnom #happyhour #gratitude #happythanksgiving #grateful
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It's never a bad time to indulge in hot, fresh cookies from the oven.... right?! Luckily, you'll get them every day on your wine & appetizer tray. If only we could share smells instead of pictures!⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #weekendgetaway #wanderlust #getaway #boutiquehotel #luxury #beautifuldestinations #adventure #bestvacations #summerfun #escape #galenacountry #galenaillinois #stayselect #selectregistry #yummy #yum #nomnomnom #happyhour
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Just a few of the magical photos shared from recent guests, who were here sharing their babymoon with us. Read through their comments about their stay below - but really, it's us that should be thanking THEM, for sharing this amazing life moment with us. Talk about a #gratitude post! ⁠

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On top of “Love-birds,” Laura and I added “Jail-birds” to our list of monikers this week! 😂⁠

We are staying in an old Galena jail converted into a B&B!⁠

Our specific room used to be the Sheriff’s family’s quarters on the second floor!⁠

The architectural beauty of the original building was preserved during the restoration and no detail was overlooked!⁠

The inmates were housed on the third floor directly above our room. The 15-foot brick ceiling you see in our room served not only as a decorative accent, but also as a security feature so the prisoners couldn’t tear up the floorboards above and sneak into the Sheriff’s house.⁠

We also found out Jail Hill Inn is the No. 1 B&B in the US and No. 2 in the WHOLE WORLD! So far, we see why! Everything has been top-notch!⁠

Aside from our beautiful accommodations, getting to spend our last trip together, before Henry arrives, has been magical also!⁠

Laura and I are so blessed by our little miracle and by the love and support we’ve received from all of you, our family and friends! Thank you!⁠

#📷 @richterfam )⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #wanderlust #getaway #boutiquehotel #luxury #beautifuldestinations #adventure #bestvacations #escape #galenacountry #galenaillinois #stayselect #selectregistry #babymoon #celebrate #specialmoments⁠
#mommatobe #cantwaittomeetyou
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It's been a while since we've shared a review, but this one from earlier this year is just too good not to share. ALL of our guests deserve nothing but the best, and we think everyone should feel like royalty! 👑⁠
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#jailhillinsta #chicago #Midwest #Midwestgetaway #getawaydestination #chitown #travel #illinois #midwestisbest #midwestlife #weekendgetaway #weekend #weekendvibes #weekendfun #wanderlust #getaway #boutiquehotel #weekendtrip #weekends #luxury #beautifuldestinations #adventure #bestvacations #summerfun #escape #galenacountry #galenaillinois #stayselect #selectregistry
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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.