Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travelers and are ranked within the top 10% of properties on Tripadvisor.
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travelers and are ranked within the top 10% of properties on Tripadvisor.
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.
Star ratings are intended to indicate the general level of features, amenities, and services to expect. This property is classified according to Giata.
Places to stay are graded on a 0-100 scale. The higher the grade, the easier it is for travelers to find restaurants and things to do within walking distance.
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Jail Hill Inn has won the hearts of many travelers with its impeccable service and sumptuous breakfasts that add a touch of luxury to their stay. The hotel's cleanliness is regularly highlighted, with guests appreciating the immaculate rooms and spa-like bathrooms. Reviewers are captivated by the exquisite decor and personal touches found in the rooms, enhancing the overall comfort.
The warm and inviting atmosphere, alongside the comprehensive amenities, including evening treats, contributes to the Inn's charm. Guests also believe the Inn provides exceptional value, offering an experience that surpasses expectations for the price.
Atmosphere
Inviting
Rooms
Luxurious
Value
Exceptional
Cleanliness
Immaculate
Service
Attentive
Amenities
Lavish
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The meticulous attention to detail is what sets Jail Hill Inn above all others. The discerning traveler will notice these details upon arrival. The exterior landscaping & 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.
Matthew, the proprietor, is the most personable host a traveler could ask for. Our greeting during check-in was a warm and inviting welcome, & 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 & details: Do you use a white noise machine? 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.
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, & firm. Obviously, this is a personal choice and I entrust that you 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! 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. 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.
Jail Hill Inn IS the benchmark in which all other B&B's are measured by.
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Date of stay: August 2024
Value
Rooms
Location
Cleanliness
Service
Sleep Quality
Trip type: Traveled as a couple
Room Tip:Â Be sure to sign the traveler's journal in each room!
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
This was the third time we stayed here, and every time has been an absolutely perfect, magical experience! The innkeeper, Matthew, has fantastic attention to detail that is obvious in each room, every space, and amenity. We feel incredibly spoiled every time we are here, from the spa bathrooms and luxurious beds to the amazing breakfast and cocktail hour spread. We particularly enjoyed the tray of goodies and bottle of wine every evening.
We always feel so welcomed here. Matthew truly makes you feel at home from the second you arrive! It is clear he genuinely cares about his guests as well as the community of Galena. Jail Hill Inn is perfectly located right in town, allowing guests to walk to the many restaurants and shops downtown.
This our favorite bed and breakfast, hands down! We can’t wait to stay in all six suites!
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Date of stay: December 2020Trip 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 as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Jan 4, 2021
Emily! It was such a pleasure hosting you and Jeremy for a little pre-Christmas relaxing getaway. I am so thrilled you both had another magical experience. Making sure every guest has an amazing and personalized experience is my goal everyday and I am so grateful to be able to share my passion for detail, history and all things amazing with both of you! As an innkeeper, I am so honored to see so many return guests coming back as I am checking people in everyday....such a perfect scenario....the guests love it here, I love creating the magic here and the community benefits from all of the above. :-) Health and happiness in your 2021 and look forward to welcoming you both back for your 4th visit sometime. Cheers and all the best, Matthew Carroll
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The best compliment I can make is that after getting home from our stay, we made another reservation a couple of months from now!!!
Matthew (along with his “behind the scenes” helpers) made every effort to make our stay memorable from the history of the location and down to all the details that are included with your stay. The afternoon “happy hour tray” was not only meticulously crafted and tasty but also supported a local store in the community! We were pleasantly surprised to see how comprehensive the wet bar area was that included disease/glassware/utensils if you wanted to bring takeout to dine in your room and even had ice for cocktails in the freezer!
The breakfast alone is enough to carry you through to the appetizer tray in the late afternoon and is impressive that the three courses change daily! Some breakfast and cookies have reached cult following and look forward to what delicious creations await our next stay. We appreciated Matthew’s engagement, helpfulness, historic overviews, hospitality and making every effort to make people feel safe as we traverse this pandemic. Bless your thoughtfulness of creating personalized trays that you carry up and down all those stairs to ensure everyone has the personal touch. We always tried to take our trays back down to save him a trip. 🙂. We look forward to our next stay! Valerie & Mark
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Date of stay: March 2021Trip 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 as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Mar 26, 2021
Oh Valerie and Mark, Reading your review made my heart so happy and humble and really reminded me why I do, what I do....to read this amazing review and am so grateful to be able to share my love for history, luxury and all things great in the world with all of the guests here! Your time away is very important and especially after this the crazy year we have all had and making sure every last detail is covered is my mission everyday. I am so excited to welcome you both back in a couple months and I completely agree that the best compliment is making another reservation and I couldn't be more honored and look forward to creating another amazing experience for you both, how fun! In the meantime, take great care and be well and I will do the same and thanks again for sharing your time and sending this review. All the best! Matthew Carroll
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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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Date of stay: February 2020Trip 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 as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Feb 24, 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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My husband of 52 years decided to treat me for Valentine's Day. So we spent the night there on Feb. 13th. Matthew was a perfect host and had lots of suggestions for us. We could not have had a nicer place to stay. The suite was over the top and the food was absolutely delicious. The evening started with a wine and cheese gathering. Some of my favorite cheeses, plus fruit and yummy cookies, which were there all evening. Breakfast of steel cut oatmeal with bananas foster was simply yummy. A chocolate croissant and the egg strata dish was delish, everything seasoned perfectly. Compliments to the chef, Matthew. Loved the room, plenty of room but still quite cozy. The bed was amazingly comfortable as well as the pillows. We were so tired after dinner we didn’t get a chance to use the hot tub but the shower was wonderful. Plus all the add-on amenities. My daughter is a huge Aveda fan so I had to rob them of all of the products. She’ll be thrilled. There is no downside about this place. There's so much history to it plus the town of Galena. Lots to do and see. Plus a variety of restaurants to fit every appetite. We ate dinner at the Log Cabin steak house. Great meal and service. If you go, ask for room 302. The windows are on 3 sides and overlook Galena and across the river to Grant's home. There are stairs to climb but well worth a little exercise. We're in our late 70's, if we can do it, anyone can. In the dead of very cold days we had bright sunshine and it lit up the rooms. Check the website out, It tells you everything I didn't. Thank you Matthew!! Loved it and are planning an annual event.
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Date of stay: February 2020
Value
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew C, Owner at Jail Hill Inn
Responded Feb 16, 2020
Peggy! Thank you for sharing this incredible review! Wow! It was such a pleasure hosting you both and how neat is that that you only live several miles away. It is so fun to welcome guests from near and far literally and because Jail Hill is truly and experience, compared to other forms of lodging, we are in the business to create lasting memories in a one-of-a-kind-expereince. I am so thrilled you loved every last aspect of your stay from our menus to the bedding. Yes, Suite 302 is a very special room for sure and luckily so are the other 5 suites as well. Each space was creating with the guest's experience in mind and that has created the TripAdvisor's Top Rated #1 B&B/Inn in the USA in 2019 and #2 in the World by the travelers that have stayed with us. So incredible by all means and look forward to continuing to share our little slice of heaven here for many, many years to come! All my best and have a fantastic rest of the winter season! Cheers, Matthew Carroll
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We wanted to get away after Phase 3 finally occurred in Illinois. Our first thought was to head to Jail Hill Inn for our 6th visit .We have been aware of Mathew’s high standard of excellence and complete devotion to his guests previously. He didn’t disappoint us in regard to the upmost care that he demonstrated to ensure the safety of his guests. We really appreciated all the hand sanitizers that were placed around the inn and in our room. The varying seating options for breakfast and cocktail hour. We personally liked the option of the cocktail hour tray being brought up to our room each day at 4:30. Once again we had a great time biking along the Galena River and then kayaking the river.
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Date of stay: June 2020Trip 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 as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Jun 13, 2020
Leslie and Dave! I love this review so much and even more importantly, I love how much you both love Jail Hill Inn and everything we are doing and adapting to in the new world we are living in right now. Making sure our guests feel pampered and protected is my number one goal each day. And how exciting that this stay now marks your 6th stay, which now puts you in our exclusive Repeat Offender guest status! I can't thank you enough for making Jail Hill Inn your getaway of choice since we opened our doors and during COVID-19. I look forward to welcoming you back for your complementary stay very soon! Have a fantastic summer season! All my best, MatthewCArroll
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My fiance and I chose to travel here for a birthday weekend escape, and it was absolutely incredible. The innkeeper was very attentive in helping us plan our activities, both in terms of finding the right things to do and in terms of navigating the local COVID restrictions. The feel of the inn was just perfect. It was absolutely as luxurious as you'd expect for the price, and played into the location's history as a jail the right amount; nothing felt tacky. Both the breakfasts and the afternoon snacks were tasty, as well.
The location of the inn just past the end of the main tourism street made for easy walking access to our in-town activities but at the same time gave us enough distance from the bustle of the area when we needed it.
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Date of stay: November 2020
Value
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Feb 25, 2021
Carl, Thank you so much for sharing your kind and heartfelt review! It is so wonderful to ready that your experience was absolutely incredible! Making sure every single guest has the best possible experience at Jail Hill is so important. Additionally, making sure we do our job to keep our guests and ourselves safe with COVID protocols and make it relaxing and luxurious along the way is important. Your time away is is important right now and there are many choices for lodging all over and I am most grateful you both chose Jail Hill Inn for your special birthday weekend escape and I look forward to welcoming you both back when you can getaway again! Cheers to the upcoming Spring season and all the best! Take care, Matthew Carroll
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Excellent accommodations. Spacious rooms. Room amenities were excellent. There was nothing lacking. Hand sanitizer was plentiful, even bug spray available on patio. Owner (Matt) provided excellent breakfast and a Wine & Cheese reception. Due to Covid, reception tray was delivered to room. Inn is located one block off main street where restaurants and shops are plentiful. Would recommend for anyone to stay.
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Date of stay: August 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Aug 15, 2020
Richard & Diann, Thank you much for sharing this wonderful review, how kind. I am so thrilled you both had such a fantastic time at Jail Hill Inn and got to get away. Making sure the guests have everything they may want or need available to them is very important as your time away is so special, especially during these unique times we are in. Making sure every single guest has an experience that exceeds their expectations is so important. I look forward to welcoming you both back again when you are in this area and creating another amazing stay for you both. Have a fantastic rest of the summer and I will do the same! Cheers and take care, Matthew Carroll
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After seven months stuck working and socializing at home, it feels great to once again be writing a review. For our first travel experience in the Covid era we wanted something fairly low key and without huge crowds. We chose perfectly, Galena, Illinois and the Jail House Inn. If you have never been to Galena you have to imagine what Main Street America would have looked like in the 1850’s. There is one main road with stores and restaurants on both sides. Adding to the charisma of the town is the fact that not a single chain store or Starbucks could be seen. If you still can’t picture Galena, imagine Main Street USA at Disney but real. The Jail Hill Inn sits just off the end of Main Street. The owner operator, Matthew, took an abandoned jail house and turned it into an absolutely elegant B&B. On the outside, the building resembles the old jail with its brick exterior. The inside, however, has been completely transformed consistent with Matthew’s vision of luxury and style. Simply put, he nailed it. Each of the 6 suites is perfectly coiffed. Our suite had a small sitting area and a large bed with the softest sheets we have ever slept in. The bathroom rivals those in the fanciest 5 Star hotels, compete with steam shower. Not a single detail was missed. You start the day with a delicious 3 course breakfast prepared by Matthew and his parents in the small kitchen located off the main dining area. Homemade muffins, croissants, eggs Benedict, and vegetable quiche are just a sampling of what Mathew and his family serve up. After a day of shopping, Matthew serves a beautiful cheese and meat tray with a bottle of wine. One item in particular warrants mention, the smoked salmon on boursin cheese atop a parmesan crisp. Delicious! In summary, if you are looking for a day or two away, you would be hard pressed not to enjoy Galena Illinois and Matthew’s Jail Hill Inn.
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Date of stay: October 2020Trip 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 as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Nov 12, 2020
Heidi and Ken! Truly what an honor it was to be your first getaway after 7 months of not traveling and be stuck at home working, etc, because of COVID. Such a crazy and unique year 2020 has been for sure! How fun to read our charming little town of Galena is like Main Street USA at Disney, but real. I totally agree. We call it the "Town that Time Forgot" and we are so blessed to have so many small shops, artists and passionate people that see why the historical charm is so important here. Just like Jail Hill Inn and how important our history and story is here in addition to all the amazing amenities, offering and tasty goodies we share with all the guests everyday here! Additionally I am so pleased that you enjoyed our smoked salmon with Boursin on the parmesan crisp so much! I agree it is pretty sensational and pairs perfectly with our evening wines we bring to the suites each night too! Take good care and have a wonderful Thanksgiving and Christmas season and I will do the same and look forward to welcoming you both back again sometime as well! Cheers, Matthew Carroll
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This was our second trip to Jail Hill Inn, and first during the pandemic. We must say, that THIS visit topped our first! We enjoyed all of the luxurious amenities offered by the Inn, including the in room champaign and chocolate assortment that greeted us in the room, the DEEP whirlpool type tube and bath products, and the sheets on the bed—(honestly, they make it difficult to want to get out of bed in the morning!).
Matthew (the innkeeper) goes above and beyond to make sure no detail is missed, even during the pandemic. He has even furthered his level of service by offering in room happy hour offerings, and even delivering breakfast to the rooms, if that helps to make guests feel safer and socially distant. We took advantage of the in room dining one morning, but we honestly prefer dining in the luxurious first floor.
The decor in this place is simply amazing. We are especially partial to Suite 401 and it’s cozy fireplace and comfortable sitting room furniture. So partial in fact, that we are opting to spend another weekend at the inn during the month of December 2020, and have precooked weekends for 2021!
If you need a getaway (and even if you think you don’t) I would HIGHLY recommend investing in a stay at the Jail Hill Inn in Galena, Illinois. You will NOT regret spending the money, and making memories at this place. Oh.. and PRO TIP for your first stay— make sure and ask Matthew about the history of the building. In addition to his skills as an innkeeper, he is a wonderful storyteller!
One last thing—- buy a Jail Hill Inn coffee mug on your way out. I promise— it’s my favorite mug now. Holds temperature of your warm beverage and stands up really well in the microwave!
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Date of stay: October 2020Trip 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 as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Matthew Carroll, Owner at Jail Hill Inn
Responded Nov 16, 2020
Sean! Thank you, thank you! What a kind and amazing review and it is such an honor it is to read every word, honestly. To see your last stay a couple weeks ago topped your first stay and even as we have adjusted a few things because of the pandemic, is so nice to read. I am grateful to have found my calling in life and being able to create and provide a unique small scale lodging experience that is Jail Hill Inn, is such an incredible opportunity I am so excited to share with my guests everyday. Your time away is so very important these days and there are many options for lodging all around and I am humbled and grateful to be able to share the passion, the beauty and history that is Jail Hill Inn with every single guest that visits here. I look forward to welcoming you both back in a few weeks for the Luminaria Weekend! How fun! Thanks again and see you both soon! Cheers, Matthew
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Hello MattyVan
Thanks for reaching out and yes, we are delighted to accommodate any dietary concern and I do see many guests with celiacs disease that stay with us and enjoy their worry free getaway with us. I am very familiar with the protocols, cross contamination measures, etc. Your menus will be amazing and that's what is nice with a small, 6 room property here as we can focus our attention on every single guest here compared to larger hotel or vacation rental properties.
Feel free to reach out to me with further questions as I am delighted to help out anyway I can.
Take a look at our website for photos of rooms, available dates and more details and photos!
Take good care and thanks for reaching out!
Matthew Carroll, owner
Jail Hill Inn
Hi there! Yes, we are delighted to accommodate an early departure breakfast and pass along some wonderful goodies for the road and stock some breakfast items in your suite the night before as well. Let us know any additional questions we can answer. Thanks!
Thanks for your inquiry with Jail Hill Inn. Given the historic nature of the property, there are no elevators on site. The suites on the second floor only require one flight of stairs to navigate. There is one handicap accessible room on the first floor as well.
There are more places to choose from in the Galena area.
LOCATION
United StatesIllinoisGalena
NUMBER OF ROOMS
6
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Which popular attractions are close to Jail Hill Inn?
Nearby attractions include P.T. Murphy Magic Theatre (0.2 miles), Matthew's Haunted Pub Crawl (0.2 miles), and Galena / Jo Daviess County Historical Society and Museum (0.3 miles).
