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$425
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Traveler (638)
Dining (165)
Videos (3)
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About

#2 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
City View
Historic Hotel
Languages Spoken
English
614Reviews3Q+A100Room tips
Traveler rating
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Popular mentions
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Most Recent
Kevin S wrote a review Jan 17
Experience at the Jail Hill Inn was spectacular. From the amazing breakfast, the evening appetizer and the hospitality provided by Matthew, all were amazing. It was tough to leave, we truest enjoyed this 5 star experience. The rooms are extremely spacious and the decor is top notch, everything was very thought out when planning/developing this Bed and Breakfast. I would recommend the Jail Hill Inn to anyone, whether it’s their first time at a Bed and Breakfast or if they’ve been to many. It really helps that the Jail Hill Inn is just a block away from downtown Galena Highlights: The service/hospitality, the food, the rooms.
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Date of stay: January 2023
Value
Location
Service
Trip type: Traveled as a couple
Room Tip: Ask Matthew about recommendations on where to go for dinner/events. He’s well versed in Galena.
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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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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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Kevin S wrote a review Jan 10
What an amazing experience Jail Hill Inn was for my husband and I. The welcoming atmosphere, the decor, the tasty food, the accommodations. Everything was top notch. We felt very blessed to be there and Matthew is definitely doing his calling very well.
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Date of stay: January 2023Trip 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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Miranda O wrote a review Jan 9
My husband and I had an amazing weekend celebrating 10 years together and our “baby moon.” Matthew ensures every detail is perfect. From the appetizer, decor, to the sheets, and OH. MY. the breakfast is absolutely top notch!! We will be back!
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Date of stay: January 2023Trip 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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Joan wrote a review Jan 5
Urbana, Illinois1 contribution1 helpful vote
If you are in need of the caring ministrations from an innkeeper who is at the top of his game in every arena, the Jail Hill Inn is the place for you. My husband and I just completed our third visit over the New Year, and once again cannot share enough accolades about our experience. Matthew, the owner and innkeeper, has thought of every detail to give his guests the ultimate experience in luxury; from the amazing 3-course daily gourmet breakfasts, the separate water closet (for privacy!) and silent fans in the bathrooms, the beyond-comfortable beds, the evening goodie trays and the ability to pipe your own music into your suite, Matthew has created a true oasis from the world of daily living. His ability to meet the needs of his guests is unparalleled, and it's clearly evident that he values each one of us. A stay with him is worth every penny as you will leave your time at the Jail Hill Inn completely restored and rejuvenated.
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Date of stay: January 2023
Value
Rooms
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
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Kori B wrote a review Jan 1
2 contributions1 helpful vote
Great experience! Every detail was covered and service was top notch. Great location, walking distance to everything downtown. Rooms were spectacular, every breakfast was delicious. Thank you Matthew for being such a wonderful host, having so much pride for what you do. It plays a huge part in the experience!
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Date of stay: January 2023Trip type: Traveled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
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Brett D wrote a review Dec 2022
The place was spotless, everything was perfect and top of the line. The breakfasts were some of the best I’ve ever had. Can’t recommend it enough. 1 minute walk to all the activities in town. Great host. Nothing to comment on that would need improved. Well done sir.
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Date of stay: December 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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Ryan C wrote a review Dec 2022
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
Service
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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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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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 2023 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 (0.3 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 The Old Blacksmith Shop (0.1 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.