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Jail Hill Inn

319 Meeker St, Galena, IL 61036-1847
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#1 of 31 B&Bs / Inns in Galena
Travelers' Choice 2019 Winner
Certificate of Excellence
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
Adults only
Private check-in / check-out
Special diet menus
Non-smoking hotel
Outdoor furniture
Sun terrace
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448Reviews2Q+A85Room tips
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Popular mentions
My husband and I had a business trip to LA cancel last week so we decided instead to go to Galena, IL for a couple of days. Based on many fabulous reviews, we booked a 2-day stay at the Jail Hill Inn. Wow!! What a beautiful inn. Perfect location too. Matthew has thought of literally everything to make his guests feel welcome & cared for. The 6 rooms were absolutely beautiful, cozy and comfortable. (We looked at them all). Everything was spotless and the decor so perfect for the setting. Just lovely. A three course breakfast, truly better than any five star restaurant, was such an amazing start both mornings. Matthew is proud of his community & suggested several spots for us to visit as well as where to dine. We had an excellent dinner at Fried Green Tomatoes (as the name suggests, do not miss the fried green tomatoes). We were sad to leave but are already thinking of when we can return for a visit. Maybe in the fall. If we can only give a five stars rating, we give Matthew and his Jail Hill Inn six.
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Response from Matthew Carroll, Owner at Jail Hill Inn
Responded 2 weeks ago
Dan and Becky! How humbling! I am so pleased to read that you both had such an amazing time during your recent getaway to Jail Hill Inn. During these times of uncertainly, it is so refreshing and comforting to have a place where you can come and relax and feel rejuvenated and at ease. Galena Illinois is a tank of gas or less away from Chicago, Milwaukee, Des Moines and so many Midwestern cities and our small town vibe is exactly what travelers are looking for. With Jail Hill Inn and our 6 suites, being 1/2 block to downtown, it is easy access to historic sites, wineries. restaurants and so much more. I look forward to welcoming you both back again and hopefully this fall or sometime soon! Also, what an honor to see you rate Jail Hill Inn 6 out of 5 stars. My goal is to create an amazing five star experience for each and every guest that stays at Jail Hill and so glad to here that we exceeded that 5 star experience. All the best and stay healthy, Warm regards, Matthew Carroll
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Property's Favorite Review
My wife and I visited Jail Hill after reading about the national and worldwide recognition in the Chicago Tribune. We decided to visit during low season to spend time together before the birth of our third child. I cannot imagine a better experience at a B&B than the one we had at Jail Hill Inn. Matthew and his family have truly created a gem, one that should appreciated for years to come. The historic nature of the property, well appointed decor, cleanliness, attention to detail, overwhelmingly delicious treats during an evening social hour and at breakfast, and conversation and guidance from Matthew made this experience one of a kind. Matthew’s humility and obvious hunger for excellence and consistency made for an easygoing relationship and sense of calm. He also paid very careful attention to my wife’s dietary needs and our overall life, looping elements of what we had shared with him during conversation with us while visiting. Our weekend was relaxing, quiet when we wanted, and we found company and conversation with other guests to help enhance our stay. This truly exceptional experience keeps us longing for our next opportunity to visit and will drive us to sharing our story with our friends and family. We can’t wait to go back!!
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Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Feb 23, 2020
Jakob and Mackenzie, Thank you, thank you- reading your sincere and heartfelt review confirms that I have found my calling in life and one where I am able to share so much greatness with every single guest that visits Jail Hill Inn. From our unique and one-of-a-kind history as a former county jail, our carefully curated amenities and decor, our tasty gourmet meals and goodies to caring and genuine connections I enjoy making with guests everyday - Jail Hill Inn is the true definition of "Experience Travel and Lodging" The Galena area has many lovely hotel AirB&B and Bed and Breakfast travel options out there and I'm so honored and humbled when I hear so many times that Jail Hill Inn is the main reason guests visit and Galena and the area are a bonus to explore and enjoy. I look forward to continuing to share the passion, the elegance and the integrity that have become so important here at Jail Hill Inn and being your destination of choice in the future. All the best to you both and to the arrival of baby #3 in April! Cheers and all my best! Matthew Carroll
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Such a charming place for a much needed mini-break. The room was amazing; 800 sq feet! Decorations were tasteful and thoughtful. The host Matthew is very charming and you can tell he loves this place. Very convenient to Main St for restaurants and shopping. It did have some parking out front, and across the street. Breakfast was wonderful, definitely did not need lunch. Bar in room, with microwave, refrigerator and freezer. Keurig with awesome choice of drinks. Wine and nibbles available at check in. Would highly recommend!
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Response from Matthew Carroll, Owner at Jail Hill Inn
Responded 3 weeks ago
Deno and Ann! Thank you so much for sharing your review and it was so fun and such a pleasure hosting you both this past week! I am so thrilled you both were able to enjoy all the amazing amenities and offerings we are so proud to share with our guests here. From the amazing amenities throughout the property, to the decor, architecture and one-of-a-kind history, Jail Hill has some to offer everyone. I look forward to forward to welcoming you both back again when you visit the Galena area! All the best, Matthew Carroll
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This was our first stay at Jail Hill and we can not say enough nice things about them. Excellent location. Fantastic breakfast. Wine and finger foods each evening. Comfortable, peaceful rooms. Owners are welcoming and truly dedicated to providing a excellent service! We booked our return stay before we checked out! Thank you for the relaxing weekend!
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Response from Matthew Carroll, Owner at Jail Hill Inn
Responded 3 weeks ago
Jeremy and Jodie, Thank you so much for sharing this review and I am so humbled and pleased that you both had such a fantastic getaway at Jail Hill Inn this past weekend. How fun and exciting that you will be back to stay in just few weeks and thank you so much! Making sure each guest experience is amazing and the best we can provide is my complete goal everyday. From the lovely menus we create to the various amenities we offer, every last detail has been stressed over for your absolute comfort and enjoyment. I look forward to seeing you both in just a couple weeks! All the best! Matthew Carroll
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My boyfriend and I just returned home today after an amazing weekend getaway stay at the Jail Hill Inn! Every detail from the ultra comfy sheets, the relaxing piped in music to each suite to the Aveda bath products in the luxurious bathroom were top notch. All my expectations for this weekend were exceeded. We stayed in Suite 201 and I knew as soon as we walked in the it would be difficult to leave. Matthew was the ultimate host. He was very friendly and he made us feel right at home. The happy hour snacks and the 3 course breakfasts were simply delicious. I couldn’t imagine staying anywhere else while in Galena. This B&B deserves all the high praise that it has been given.
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Response from Matthew Carroll, Owner at Jail Hill Inn
Responded 3 weeks ago
Susan, Thank you so much for sharing this review! It was such a pleasure meeting and hosting you both this past weekend and so thrilled to read that all your expectations were exceeded! That honestly means so much to me and my parents and entire support system at Jail Hill Inn. Making sure every single guest has the most amazing and genuine experience they can possibly have at JHI is my number one goal everyday. From our menus everyday, to the amenities and products throughout the property to the building design and furnishings, every single thing you see, taste, touch and hear at Jail Hill has been thought of and stressed over to make sure it is the best of the best. I look forward to welcoming you both back again and have a fantastic Spring season! Cheers, Matthew Carroll
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$327 - $466 (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 Log Cabin Restaurant.
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).
Is Jail Hill Inn accessible?
Yes, it offers reduced mobility rooms. For specific inquiries, we recommend calling ahead to confirm.