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319 Meeker St, Galena, IL 61036-1847
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COVID-19 update: See the added health and safety measures this property is taking.Read more
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Traveler (555)
Dining (139)
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What is Travelers’ Choice Best of the Best?
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What you can expect during your stay
  • Regularly sanitized high-traffic areas
Updated 06/12/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
Updated 06/12/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#1 of 31 B&Bs / Inns in Galena
2021 Travelers' Choice Best of the Best
GreenLeaders Bronze level
Welcome to Jail Hill Inn, a luxury small inn one block from historic Galena, Illinois. Prominently situated to overlook Galena and its countryside, Jail Hill Inn offers gracious lodging for your perfect getaway to Galena. The 135 year old, 4-story brick building that served as the county jail for nearly 100 years has now been completely renovated in 2015 with amenities that will thrill any traveler.
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Room & Suite (129)129
Full view
Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Horseback riding
Full body massage
Adults only
Non-smoking hotel
Electric vehicle charging station
Happy hour
Special diet menus
Wine / champagne
Canoeing offsite
Outdoor furniture
Sun terrace
Private check-in / check-out
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Room features
Allergy-free room
Soundproof rooms
Air conditioning
Coffee / tea maker
Cable / satellite TV
Whirlpool bathtub
Seating area
Separate dining area
Separate living room
Wardrobe / closet
Bottled water
Private bathrooms
Tile / marble floor
Wake-up service / alarm clock
Flatscreen TV
Bath / shower
Complimentary toiletries
Hair dryer
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Room types
City view
Non-smoking rooms
Good to know
City View
Great View
Languages Spoken
531Reviews3Q+A94Room tips
Traveler rating
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Popular mentions
Lara W wrote a review May 8
Orland Park, Illinois37 contributions2 helpful votes
My husband and I stayed at Jail Hill Inn May 1st and 2nd and wished we could have moved in permanently! This was our first stay at the Inn and it greatly exceeded our expectations. This stay was pure luxury! Matthew the Innkeeper/owner created a beautiful B & B which would rival any 5-star boutique hotel. We stayed in suite 201 which was home to the sheriff and his family. It was stunning! It's a corner suite with large windows allowing for natural light. The ceiling is brick!!! So cool! The bathroom and bedroom spacious and comfortable. The pillows were SO comfortable and the sheets SO soft that we bought some for home! Matthew pampers his guests by giving them champagne and chocolates upon arrival. There were fresh flowers in the suite...very lovely touch and smelled SO good! Every evening you're treated to a wine and cheese tray brought to your room! My husband and I particularly enjoyed having the tray in our room since we were able to tuck the food in the fridge and enjoy it later at night. The breakfasts were beyond yummy and they're HUGE!!! You will not be hungry until dinner! This was only our second stay in Galena...last time was 10 years ago. Downtown Galena is thriving and ready for guests. It won't be another 10 years before our next visit! Matthew...we plan on being "repeat offenders"!
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Date of stay: May 2021
Room Tip: Only a brief walk to Main street. Suite 201 doesn't have a view overlooking Galena...pick a...
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candicezg wrote a review Jan 2021
il2 contributions2 helpful votes
Property's Favorite Review
This beautiful inn is clearly a work of love for innkeeper Matthew Carroll. We were familiar with Matthew’s expertise as an innkeeper and first visited Jail Hill Inn shortly after Matthew ventured on his own and undertook the extensive renovation of the jail. The rough plumbing and basic structure that we saw has been transformed into the most luxurious inn with six very private suites. Each 800 sq ft suite boasts 3 rooms and is meticulously decorated. The details in the suites are impeccable – incredible and unique use of light, top of the line Kohler tubs, showers, and fixtures, and linens that encourage you to melt into the bed. I could go on and on. Our visit was actually a last minute decision because of an unpected day off. We were incredibly please with our spacious room on the 4th floor and cannot wait to explore the rooms on floors 2 and 3 which featured even higher ceilings. We were also fortunate to visit in early January on the last weekend that the inn was decorated for Christmas. In addition to decorations abundant throughout the common areas of the inn, each guest suite was also tastefully decorated for the holiday. Our favorite treat is the over-the-top 3 course breakfasts that are classic, yet unique and always feature the finest and freshest of ingredients. We were also treated to a wine and cheese tray that was delivered to our room and featured a bottle of house wine a charcuterie selection, fruit, fresh appetizers made at the inn, and a few of Matthew’s mom’s decadent cookies. Although our stay was brief, I could continue to elaborate on the many details of this beautiful escape. But, I will stop here, and not divulge any further details because part of the fun is the surprises that you will encounter in this magical place. Matthew has created an amazing environment with his incredible sense of design and style and great appreciation for fine cuisine. He also does not take his past success for granted and is always looking ahead and acting upon the latest trends in travel. This place is an absolute gem!
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Date of stay: January 2021
Sleep Quality
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Jan 26, 2021
Candice! It was so fun hosting you and Jack here at Jail Hill Inn and wow, what an amazing and heartfelt review you shared- thank you for detailing the love, beauty and passion that has created Jail Hill Inn. I truly consider Jail Hill Inn my greatest honor in life. Being able to take something, from basically nothing and give it life, love and to be able to share it with everyone that visits, is a pretty incredible feeling! Your time away, even if it is just one night, is so very important and making sure every detail is thought of and taken care of is my mission everyday. We all have so many choices for good lodging out there and creating an experience that goes above and beyond is what travelers want these days, especially during the unique times we are in. I never want to settle with the "status quo" and strive to make each day, greater than the last. From the wonderful afternoon treats to the 3 course gourmet breakfast....making sure it is the best of the best with every dish we share, is our mission. Thanks again for taking the time to share this review and I look forward to welcoming you both back and sharing more of JHI with you both! Take good care and I will do the same, Matthew Carroll :-)
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Nomad56619 wrote a review Apr 2021
21 contributions
First off I have to say our first stay this past weekend at Jail Hill Inn was amazing! We have very good friends who have been telling us about it for the past few years so finally we decided to give them a try and it did not disappoint. First off the location is prime and just one block off of Main Street on the North end of it so that covers the location aspect. Five stars on location. Second the building and interior of the Inn was outstanding. The lobby is completely beautiful and contains some beautiful pieces of furniture and decorations. In your room you will find a spiral bound book of stories of events that happened at the jail from 1860 to 1975 with some great content. Another five stars! Third, the suites themselves. It was recommended by our friends to stay in Suite 201 and I have to say this Suite was top notch but from what I can tell all of them are top notch so on our next visit and there will be a next visit we will try a different suite possibly on the fourth floor. All of the furniture was expertly picked out as were the decorations and accommodations in the room. Everything was just beautiful. Fourth which in my book should be first is the food. The breakfasts are to die for and quite honestly more than I could eat in a single sitting so I was selective about what we took to go. Then there is the charcuterie/snack tray and bottle of wine which again is top notch and more that you can snack on in a single setting if you intend on going out to dinner in town so again plenty of food that was left over and had snacks for home when we got back to Chicago. Crazy good stuff and another five stars.! And lastly the Innkeeper Matt. Matt is a great guy and the mastermind behind this gem for sure and he took great care of us while we were there. Matt is very personable and has a great head on his shoulders so all in all five stars on all categories. Looking forward to our next trip to Jail Hill Inn.
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Date of stay: April 2021
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded 2 weeks ago
Larry! Wow! Thank you for sharing this amazing and heartfelt review! Making sure your getaway is the best of the best is my goal every single day here. Your time away is so important and I am so grateful you chose Jail Hill for your Galena experience. As you mentioned, from the location, the history, food, accommodations and so much more- Jail Hill is a total experience from beginning to end. And to read that I have a great head on my shoulders is an honor, truly. If I ever have to wonder why I decided to do what I did at Jail Hill Inn, reading reviews like your's confirms I have found my calling in life and doing exactly the right thing! All my best to both of you and I look forward to welcoming you back when you can getaway again! Take good care and have a wonderful summer season! Cheers, Matt Carroll Jail Hill Inn
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Jason K wrote a review Apr 2021
West Des Moines, Iowa3 contributions
This was our third visit to Jail Hill Inn and after a long break due to COVID we were so excited to return! Mathew did not disappoint! He continues to improve upon perfection and the town of Galena is always so inviting! Thank you Mathew and know that JHI remains one of our favorite places to getaway! We will be back!!
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Date of stay: April 2021Trip type: Traveled as a couple
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded 2 weeks ago
Jason! It was such a pleasure hosting you and Joanna again and thank you for making JHI your getaway spot after COVID. Our guests, the property and the entire experience is my mission every single day here and making sure your experience is the best it can possibly be is such a reward! 2021 is shaping up to be an incredible year for small towns like Galena and small venus like JHI and I couldn't be more humbled and honored that so many people are turning to these small, experience driven getaways as we navigate these COVID times. I look forward to welcome you both back when you can getaway again and have a fantastic spring and summer season 2021 and I will do the same! All the best, Matthew Carroll
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barbarasmcfadden wrote a review Apr 2021
Iowa City, Iowa2 contributions
So, this is a great place and if you are even considering staying there do yourself a favor and book right now. Every aspect of your comfort and wellbeing has gone into the preparation of you amazing, gigantic yet oh-so-cosy suite. Champagne and water in the fridge and an amazing evening snack. And the breakfasts? Let’s just say they are amazing, tempting and worth every calorie! You will not need to plan a lunch out after indulging. Matthew is such a kind, cheerful and helpful host, and does he know the area! We intend to be “Repeat Offenders” and I bet you will, too!
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Date of stay: April 2021Trip type: Traveled as a couple
$355 - $472 (Based on Average Rates for a Standard Room)
United StatesIllinoisGalena
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Frequently Asked Questions about Jail Hill Inn
Which popular attractions are close to Jail Hill Inn?
Nearby attractions include P.T. Murphy Magic Theatre (0.2 miles), Great American Popcorn Company (0.2 miles), and Galena / Jo Daviess County Historical Society and Museum (0.2 miles).
What are some of the property amenities at Jail Hill Inn?
Some of the more popular amenities offered include free wifi, free breakfast, and free parking.
Which room amenities are available at Jail Hill Inn?
Top room amenities include a kitchenette, air conditioning, and a flat screen TV.
What food & drink options are available at Jail Hill Inn?
Guests can enjoy free breakfast during their stay.
Is parking available at Jail Hill Inn?
Yes, free parking is available to guests.
What are some restaurants close to Jail Hill Inn?
Conveniently located restaurants include Fritz and Frites, Fried Green Tomatoes, and Little Tokyo.
Is Jail Hill Inn located near the city center?
Yes, it is 0.5 miles away from the center of Galena.
Are there any historical sites close to Jail Hill Inn?
Many travelers enjoy visiting Ulysses S. Grant Home (0.5 miles), Root Beer Revelry (0.4 miles), and Washburne House State Historic Site (0.6 miles).
Does Jail Hill Inn have any great views?
Yes, guests often enjoy the city view available here.
Is Jail Hill Inn accessible?
Yes, it offers reduced mobility rooms. For specific inquiries, we recommend calling ahead to confirm.