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Traveler (638)
Dining (165)
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About

#3 of 28 B&Bs / Inns in Galena
Location
5.0
Cleanliness
5.0
Service
5.0
Value
5.0
Travelers' Choice
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
Hiking
Horseback riding
Full body massage
Adults only
Non-smoking hotel
Electric vehicle charging station
Wifi
Happy hour
Special diet menus
Wine / champagne
Skiing
Canoeing offsite
Outdoor furniture
Sun terrace
Private check-in / check-out
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Room features
Allergy-free room
Soundproof rooms
Air conditioning
Fireplace
Housekeeping
Coffee / tea maker
Cable / satellite TV
Whirlpool bathtub
Bathrobes
Seating area
Separate dining area
Separate living room
Sofa
Wardrobe / closet
Bottled water
Iron
Private bathrooms
Tile / marble floor
Wake-up service / alarm clock
Kitchenette
Microwave
Refrigerator
Flatscreen TV
Bath / shower
Complimentary toiletries
Hair dryer
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Room types
City view
Non-smoking rooms
Suites
Good to know
HOTEL STYLE
Boutique
Romantic
Languages Spoken
English
608Reviews3Q+A100Room tips
Traveler rating
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Ryan C wrote a review Dec 4
1 contribution
Our experience was beyond our expectations. When we checked in, we were created by the owner. He was extremely friendly and made us feel welcome. A 3 course breakfast was served every morning and a tray of cheese, meat, fruit and wine was delivered to our room every night. Our stay was very relaxing. We will definitely stay there again.
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Date of stay: November 2022
Value
Location
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Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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SDK wrote a review Jul 2022
Valparaiso, Indiana8 contributions1 helpful vote
Property's Favorite Review
Our stay at the Jail Hill Inn has been spectacular. Matthew, the Inn Keeper, has created a beautiful environment and cares so much about his guests. No detail is spared and the quality of everything is top-notch. The gourmet breakfasts are so good and filling we were full until dinner. Each afternoon we also had great apps and wine (a very good selection is offered) The decor, linens, amenities, quality and level of comfort and care will have us returning often. You won’t be disappointed. Location is excellent, within walking distance of so much. Also fascinating is the history of the building and the labor of love required to turn it into what it is today. More than 5 stars in our book.
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Date of stay: July 2022Trip type: Traveled as a couple
Room Tip: Parking is right outside the building.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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hpknox wrote a review Nov 2022
Woodhull, Illinois19 contributions19 helpful votes
This was our third time visiting Jail Hill Inn so we knew we were going to be pampered and our expectations were met and exceeded. Matthew, the proprietor, was so welcoming and made sure we had everything we needed to relax during our stay. We have stayed in a different suite each time we have visited; this time we were on the fourth floor. Each suite is beautifully furnished and yet just a bit different. Take the time to tour the rooms on the website, but know that the suites are even more impressive in real life. We loved the wine and appetizer trays that Matthew delivered to our room every afternoon. The gourmet three-course breakfasts were to die for. The beds were very comfortable and had the most luxurious linens. I could go on and on. There were just so many extras that came with our room that makes Jail Hill Inn special. It is easy to see why this property receives so many awards and all of the recognition. It is well-deserved. My husband and I look forward to our fourth visit in the future.
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Date of stay: November 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Emily W wrote a review Nov 2022
2 contributions
What an exceptional Bed and Breakfast, in every single way. This was my second visit to JHI and my husband’s first. I’m so glad he got the JHI experience, and he thought it was just as wonderful as I did. No detail is left untended. The check in was friendly and smooth, we had help getting our luggage up the stairs, and got settled with a warm welcome of chocolates and champagne. We stayed in suite 302 this time which was immaculate and comfortable, well-appointed with everything we needed AND MORE. Breakfast is delicious and hearty - you definitely won’t feel hungry here, and that’s part of the pampering. The afternoon wine and appetizer tray was just as delicious, and served as a great snack to have throughout our stay (we often saved things for the next day). I live far away so can’t come as often as I like, but I’m already looking forward to another luxurious few days at this incredible B&B. It deserves every review, accolade, and more. Thanks, Matthew!! What a gem.
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Date of stay: November 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Sarah S wrote a review Oct 2022
1 contribution
We just checked out after our second stay at Jail Hill Inn. We have regularly visited Galena for twenty years now, and stayed at a handful of different places. Some are better than others, but none can compare to Jail Hill, which is truly so much more than a bed and breakfast, it's an experience for all of the senses. There is nothing that hasn't been thoughtfully considered by innkeeper Matthew. Absolutely exceptional, every time. As someone with a few sensory issues, I will tell you a few things I appreciate: our suite is consistently immaculate. There is no dust in inconspicuous places and the bathroom is very clean. And believe me when I tell you, when I am staying anywhere I look the place over for inadequate cleanliness because if it's dirty I won't stay again. There is nothing worse than staying in dirty accommodations, except feeling dirty due to a subpar shower. The water pressure and temperature in a JH shower is on par or better than what you would experience at home. The bed and bedding are exquisite. Room temperature extremely comfortable. Noise level in the bedroom is non-existent, as can be light, if preferred. If you are not a persnickety person, the things mentioned above may not matter to you, however, everyone enjoys good food. Matthew's breakfast is incredible. The flavors, the presentation, the love he puts into his delicious recipes is just outstanding. I have him on standby to be our personal chef if we win the lottery. Even your grandma would be impressed by his cooking. Each afternoon comes another tray of charcuterie items, canapes, fruit, cookies and wine. Yet another lovely, delicious and refreshing touch that is offered at JH. And these are just a few things you can expect. My husband reached out to Matthew a few weeks before we came to surprise me for our 20th anniversary. When we walked in, our wedding picture and program were on display at the front desk. In our room I found a beautiful bouquet of flowers and more pictures from our wedding around the suite. It was so special and I was so touched. It was so kind of Matthew to take care of all these personal details to make our time away a real celebration. I am so grateful for the devoted job he does and the beautiful Jail Hill Inn. We won't stay anywhere else!
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Date of stay: October 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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marybethvandehey wrote a review Oct 2022
Kaukauna, Wisconsin1 contribution
We stayed at the Jail Hill Inn for our Anniversary. It was an AMAZING get away! If you want to be pampered-this is the place. The food was phenomenal, the room we stayed in was SO comfortable and all the extras that Matthew makes sure his guests receive and enjoy are there. LOVED it all. Best bed amd breakfast by far that we have ever stayed at :)
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Date of stay: October 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Lewis W wrote a review Oct 2022
Naperville, Illinois41 contributions36 helpful votes
+1
The meticulous attention to detail is what sets Jail Hill Inn above all others. The discerning traveler will notice these details upon arriving at the premises. The exterior landscaping and decor are perfectly manicured, placed, and festive for the season, (fall harvest). Step foot into the Jail Hill Inn and behold the breathtaking beauty of a perfectly decorated first floor which serves as a lobby, sitting area and dining room. One will also notice that Jail Hill Inn is flawlessly decorated throughout each floor and room. Matthew ensures that Jail Hill Inn stays properly adorned with each season throughout the year. Matthew, the proprietor, is the most personable host a traveler could ask for. Our greeting during check-in was a warm and inviting welcome, and after being assisted with our bags to our room, Matthew gave us a brief and highly interesting history of the Jail Hill Inn along with some of the features of our specific room. After leaving us to our own devices for a short while Matthew returns with an exemplary display of an afternoon appetizer tray, replete with charcuterie, a wine & cheese offering, a small dessert, and another offering (that changed daily during our visit) will start your visit with a further impression of exquisite detail. As you enjoy your tray of delicious goodies, take a look around your room and notice the amenities and details: Do you use a white noise machine at night? There's one in your room. Your choice of blankets is available for snuggling on the couch: a light, medium, and heavy weight blanket, each of the softest touch, is available for your selection. Let's discuss the bed: It just might be the best night's sleep you'll ever have. The mattress is both soft but, yet supportive, at the same time. The sheets are microfiber but, do not feel like a typical microfiber sheet nor do they feel hot like others that I have experienced. Each guest has three pillows available to them: Soft, medium, and firm. Obviously, this is a personal choice and I entrust that you, should you choose to stay, will find the right one for you. We were so enamored with the bed that we purchased a sheet set, and two pairs of pillows before we departed. I have another tab open now, preparing to purchase the comforter as well. I would hope that this gives you a proper indication of just how delightful the attention to details are at Jail Hill Inn. One last item to discuss: Breakfast. Matthew has indicated that he strives to serve the same guests a different breakfast each morning of their stay. With up to six different couples coming and going at various times, this requires a monumental amount of effort to serve everyone the same breakfast but, ensuring that no couple receives the same service as they enjoyed previously. Matthew will also accommodate ANY dietary need or restriction . For brevity's sake, I'll discuss breakfast on our second day. Our first course was a roasted pear, sprinkled with brown sugar and cinnamon. On the side was granola, coconut yogurt(dietary restrictions), and various berries. The pear was perfectly warm and sweet, while the granola, berries and yogurt provided a perfect contrast for the palate. The second course was a pumpkin and cranberry muffin sprinkled with powdered sugar. I'm normally not a fan of pumpkin but, the divine aroma compelled me to partake and I am oh-so-glad I did. My spouse and I split one muffin and saved the other for our drive home! Our third course was a herb and vegetable omelette, with roasted potatoes, and an apple chicken sausage. If any of these alternative are healthy dishes sound unappealing to you, let me reassure you that, as the World's Pickiest Eater, you can enjoy breakfast at the Jail Hill Inn and walk away knowing that Matthew has set the benchmark to which all other establishments that serve breakfast will be measured by. Long story short: Jail Hill Inn IS the benchmark in which all other Bed and Breakfast Inns are measured by.
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Date of stay: October 2022
Value
Service
Sleep Quality
Room Tip: Suite 301 has the only Kohler steam shower! All others have a chromatherapy bath.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Riley K wrote a review Oct 2022
1 contribution
Best bed and breakfast we have EVER stayed at. Breakfast is to die for, the Inn always smells AMAZING, and the cheese platter is the perfect afternoon snack. The bathrooms in the rooms are top of the line, always clean, and have the best robes. Great location too!
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Date of stay: October 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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LizNelson77 wrote a review Oct 2022
Gurnee, Illinois5 contributions
+1
The owner has created an experience that makes you feel like royalty. The rooms are stunning with beautiful, comfortable furniture. I was able to relax and rejuvenate in the soaker tub with the complimentary bath salts. The best part are the delicious homemade breakfasts with fresh ingredients. We also really enjoyed the wine and cheese trays that included products from the local shop downtown. It was a wonderful way to celebrate 20 years of marriage and we can’t wait to go back!
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Date of stay: October 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Katie M wrote a review Oct 2022
Bettendorf, Iowa10 contributions1 helpful vote
We are frequent visitors to Galena but this was our first time staying at the Jail Hill Inn. What an amazing property nestled just up the hill from Main Street. No detail has been overlooked in this place both in the common spaces and the rooms. Matthew is the owner and is so welcoming and full of information. We felt so cared for throughout our stay. The three course breakfast is like no other and the afternoon tray of snacks and wine was a highlight as well. Our room was beautiful and the bathroom was one of the best we have ever had in a hotel or B&B. It was very quiet without any noise from other guests. We enjoyed chatting with others on the back deck in the evenings but didn't feel like we had to have forced interaction with other guests as you sometimes feel at B&Bs. We will definitely be back again!
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Date of stay: October 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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PRICE RANGE
$472 - $549 (Based on Average Rates for a Standard Room)
LOCATION
United StatesIllinoisGalena
NUMBER OF ROOMS
6
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JAIL HILL INN - Updated 2022 Prices & Reviews (Galena, IL)

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), Galena / Jo Daviess County Historical Society and Museum (0.2 miles), and Matthew's Haunted Pub Crawl (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 Fried Green Tomatoes, Fritz and Frites, 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 Dowling House (0.1 miles).
Does Jail Hill Inn have any great views?
Yes, guests often enjoy the city view available here.