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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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Traveller (578)
Dining (148)
Videos (3)
What is Travellers’ Choice Best of the Best?
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What you can expect during your stay
  • Regularly sanitised high-traffic areas
  • Contactless check-out
  • Individually wrapped toiletries
Updated 12/06/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
Updated 12/06/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#2 of 32 B&Bs / Inns in Galena
2021 Travellers' 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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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 / wardrobe
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
559Reviews3Q+A99Room tips
Traveller rating
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Popular mentions
Laura GR wrote a review 4 Nov
Elm Grove, Wisconsin22 contributions9 helpful votes
This amazing place exceeded our expectations! For our "last hurrah" before baby arrives, we wanted a relaxing getaway to a small, walkable town with charm. The accommodation needed to have a whirlpool tub, king bed, and gas fireplace. Jail Hill Inn checked off those boxes AND MORE! When we reserved room 202 several months in advance, we didn't have many options left - so we stayed Sunday through Tuesday. Many restaurants are closed on Mondays, but we didn't mind because we were SO well fed at the Inn! The 3-course breakfasts were delicious and filling, so we didn't need lunch! Then we had wine/cheese daily at 4-5pm, which became our dinners! Those charcuterie boards had everything! We actually came home with leftovers! Innkeeper Matthew was wonderfully accommodating and had non-alcoholic sparkling cider available for this pregnant lady. And you can tell he is super passionate about his job and customer service. He made our stay so comfortable and amazing. Bonus features: Bluetooth sound system (we used it constantly), ability to log into AppleTV account to watch our movies, delicious box of chocolates, Aveda (and other high quality) skin care products, cozy faux fur throw blanket, unique architecture, easily walkable to Main Street, sold our favorite bottle of wine without a huge markup (The Prisoner), comfortable sheets and bed, electric vehicle charging station!
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Date of stay: November 2021
Sleep Quality
Room Tip: We loved Room 202! Spacious yet cozy. Nice views from 9' tall windows (saw a shooting star...
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candicezg wrote a review Jan 2021
il2 contributions2 helpful votes
Property's Favourite 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 26 Jan 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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Ronnie R wrote a review Oct 2021
Kaaawa, Hawaii13 contributions2 helpful votes
This is one of those things in life that you need to check off your list. The owner very attentive on the smallest of details. It’s the best of the best. We have been visiting his place now for three years. Always the same. Perfect. We keep watching for openings and we were able to get five nights in this year. You just need to keep checking. All rooms are different but all perfect. This is the only jail in the country that you pay to get into. Spoil yourself You deserve it Captain Ron
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Date of stay: October 2021Trip type: Travelled as a couple
Room Tip: There is a electric charger for guests only. One of the best I’ve used
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John G wrote a review Sep 2021
1 contribution
Loved our stay at the Jail Hill Inn. Prime location in an historic building with top of the line details in the room furnishings, breakfasts and afternoon snack tray and couteous service. Will definitely come back again for another visit in the near future. Thank you Matthew!
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Date of stay: September 2021Trip type: Travelled as a couple
Happy Traveler wrote a review Sep 2021
1 contribution
We had a fabulous stay at Jail Hill Inn. We found the history of the building fascinating. But the transformation of the space is hard to believe without seeing. And their attention to detail is impressive. The cheese and appetizer tray in the evening was delicious, and it came with wine! The room itself was clean and spacious. The bed was quite comfortable. The 3 course breakfast was incredible! Each course was something special; all were tasty and beautifully plated! We are already exploring open dates for a return visit!
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Date of stay: September 2021Trip type: Travelled as a couple
US$355 - US$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 (0.4 km), Great American Popcorn Company (0.4 km), and Galena / Jo Daviess County Historical Society and Museum (0.4 km).
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 centre?
Yes, it is 0.8 km away from the centre of Galena.
Are there any historical sites close to Jail Hill Inn?
Many travellers enjoy visiting Ulysses S. Grant Home (0.9 km), Root Beer Revelry (0.6 km), and Washburne House State Historic Site (1.0 km).
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 enquiries, we recommend calling ahead to confirm.