Jail Hill Inn a Boutique Hotel - Galena, Illinois

Annemarie S.

You can certainly see why it is number rated across many review sites. Matthew leaves no stone unturned for his guests and you can see how much dedication and work he put into making this former jail into a beautiful bed and breakfast. All the food was delicious and our room (301) was so beautiful. The biggest compliment came from my husband who is not a big fan of BNBs, he was very impressed and said we should stay here each time we go to Galena, and we’ve been coming to Galena for over 20 years now. He jokingly said let’s go back next weekend.

Shawn M.

Every now and then you meet someone who is doing exactly what they're meant to do. Matthew is one of those people. From the moment we got there, we felt welcomed and pampered and since we've both been really stressed out lately, this was just what we needed to relax and reset. The room was warm, inviting, and beautifully decorated. The charcuterie tray waiting in the room for us was perfect after our drive. The bed had the softest sheets we've ever encountered. Breakfast was not only delicious but substantial enough to keep us going until well into the afternoon. ||Will we go back? Without a doubt. And we've already started telling everyone what an amazing experience staying at the Jail Hill Inn was. ||Bravo, Matthew, Willow, and Dad!

val N.

We loved Jail Hill Inn! The food is incredible and has well thought out pairings! The evening food trays are fabulous! The room we stayed in (402) was extremely clean, beautiful decor and has a comfy bed! Very high end furnishings and attention to every detail. Matthew is an amazing host and is very personable. We will be back!

Dan

Amazing stay from start to finish! This was our first time staying here. We came to celebrate my wife's birthday and it sure was a birthday to remember. The room, snacks, treats, breakfast, and all the extra details were wonderful. Thank you, Matthew for all your thoughtfulness, kindness, and hard work into making our stay so memorable! We can't wait to be repeat offenders!

See you next time!

Judy B.

We had a great stay at the Inn! Quiet, comfortable, beautiful large room with a beautiful bathroom and great shower. Warm hospitality and delicious food for breakfast and late afternoon snacks. Loved the tray of all the goodies. So convenient for strolling Galena, exploring the area, and relaxing. Hope to return soon!

Jenna L.

This was the best hotel / BB I have ever been to!! The hubby and I had a weekend away and it was everything we could’ve asked for and more. From the big Jacuzzi bathtub to the comfy, cozy, bedding, and pillows. Matthew made sure every detail of our stay was perfect and not to mention the food was phenomenal. We cannot wait to go back.

Betty K.

From the moment you enter the front door of the Jail Hill Inn greeted by an exceptional host, ready to please at every turn, you are transported into a world of luxury.|We haven't stopped talking about our visit Sept. 2024. Our visit was nothing less than luxurious and pampered. With Matthew who is the most personable and dedicated host willing to please at every turn, he is also very knowledgeable about the area, restaurants and the like.|The whole experience of staying here is incredible! There is nothing we've experienced elsewhere that can compare. One night we even had the experience of deer outside the window of our suite which was a pleasant surprise!|From the champagne and chocolates waiting upon arrival to the charcuterie and wine that arrives shortly thereafter to your luxurious suite that is exquisitely decorated Matthew has thought of everything! |Waking up in the morning to freshly brewed coffee and freshly squeezed orange juice followed by a 3 course breakfast is the perfect way to get your day started in the inviting and beautifully decorated dining room.|If you are thinking about booking a suite for that special occasion or just to get away, don't hesitate, you won't be disappointed! We are planning a visit for our 50th wedding anniversary in 2026. I can't think of anywhere else I'd want to be.|If only I could give 10 stars!!

J N.

We needed a quick weekend getaway from Chicago. We’ve always heard positive reviews of Jail Hill Inn, not only from reviews but also from our friends that have frequented this establishment. Matthew’s attention to detail is impeccable, from the detail of the three course breakfast to the details of the rooms are exquisite. Mathew’s knowledge of Galena is also very welcoming. I can’t say enough positive words for Matthew, Mathew is incredibly thoughtful from the day you arrive until the day you depart. Mathew‘s gracious generosity has a feel of Victorian era time period… I can appreciate the careful thought and preparation that has gone into our stay.
Mahalo, Jenn & Karl