Galena Bed and Breakfast

Jail Hill Inn

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About The 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.

Each of the inn’s six uniquely appointed, luxurious three-room suites is an impressive 800-square feet and offers the finest of amenities. Every detail is attended to with genuine care ensuring Jail Hill Inn guests experience a getaway that exceeds expectations. Guests looking for ultimate pampering should consider scheduling a fully-customized, in-room massage. In an instant, your suite will transform into a tranquil spa escape.

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.

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! This incredible distinction reflects the impeccable hospitality and attention to detail every guest experiences at Jail Hill Inn.

Safety Features

In-Room(s) Climate control

About The Innkeepers

The Family Team at Jail Hill Inn

The Family Team at Jail Hill Inn

As a Galena native, I am proud to share my community, my home and Jail Hill Inn with my guests. My passion for inn keeping began after I graduated from college and joined an amazing team at a local inn. I quickly discovered an incredible way of life and realized my passion for customer service and hospitality.

In January of 2015, I had an opportunity to purchase the old Jo Daviess County jail building, which was in dire shape and in need of extensive repairs. I took a leap and purchased the property before funding was secured or rezoning was approved. Thank goodness my instincts were accurate and I received an outpouring of community support. Since I was born and raised in Galena, I wanted to patronize local businesses for the restoration. Every beautiful detail at Jail Hill Inn was designed, crafted or sourced from talented local contractors and fellow area business owners.

My parents, Terry and Ginny, have been hands-on and supportive since the very beginning. Whether it was having my dad, a retired schoolteacher, oversee some of the construction work or my mom, a retired Galena business owner, help to create the inn’s amazing breakfasts, Jail Hill Inn came to be and continues to flourish because of my parents love, support and willingness to work alongside me. They are integral in the day-to-day operations of the inn and as a family we share the same love for hospitality and attention to detail.

What an incredible dream come true this experience has been for me to see my vision unfold from idea to reality. This would not be possible without the amazing support of my loving parents, family, neighbors, friends, local contractors and fellow business owners.

I look forward to welcoming you soon to this very special place.

Warm regards,

Matthew Carroll


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319 Meeker Street, Galena, Illinois 61036


6 Guest Rooms

Popular Amenities

Accepts Gift Cards
Breakfast Included
Daily Housekeeping
Fireplace In Room(s)
Free Parking
Free Wi-Fi
Full Breakfast Included
In-Room TV(s)
King Bed(s) On Site
Smoking - Prohibited
Private Bathroom(s)


TripAdvisor 2019 Travelers Choice Award # 1 B&B/Inn in USA
TripAdvisor 2019 Travelers Choice Award #2 B&B/Inn in the World
Landmarks Illinois 2016 Preservation Award - Adaptive Use


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