One of the nicest places I have ever stayed at. Where to begin? The inn is impeccably restored. It is a beautiful building, and our suite was thoughtfully, elegantly designed and stocked with every comfort. We loved the lush fresh flower arrangements in our room and throughout the entire inn. The common areas (breakfast area/living on main floor and the outdoor patio) are similarly beautiful, with comfortable seating and beautiful vistas. The food - from the afternoon appetizer/cheese/wine tray to the incredible breakfast - was really delicious. And I could go on. If you're at all contemplating a stay in Galena, this is the place to go! It is romantic, quiet, nurturing, luxurious. read more

The facilities at Jail Hill Inn are EXQUISITE! Everything that you could possibly imagine was at our disposal. The decor was GORGEOUS! And everything was very high-end. For instance, the carpeting was what you would find in a mansion. The linens and towels were luxurious. We were provided with a bottle of wine and appetizers in the evening. There was a nice variety and a more than ample amount. Breakfast in the morning was out of this world! 3 Courses!!! Entrees were expertly prepared and delicious -- and healthy! Probably our favorite was the steel-cut oats with fruit and a banana foster sauce -- YUM! Again, these portions were very generous. Our host, Matthew, was very kind and attentive. I don't think there are enough superlatives to describe our experience! read more

A stay at Jail Hill Inn is luxurious and cozy, welcoming and intimate, sophisticated and hugge all due to Matthew and his staff. The professional attention to detail and Mathew's own passion for the well-being of his guests and his overall kindness is unsurpassed. We have stayed several times and are never disappointed--the holiday décor is not to be missed. read more

Great personalization on a local historic site. Limited to six rooms, this is five star service in an unassuming, yet five star hotel facility. Wine and cheese, plus three course breakfast included in the pricing. One block walk to downtown strip. read more

Jail Hill Inn - A nice gift waiting guests' entrance to their rooms, provisioned via Stam Fine Chocolates. - Bed & Breakfast Near Me - Galena, Illinois

What a lovely inn! Mathew your love for being an innkeeper shows through with what you have created here at Jail Hill Inn. The rooms are just beautiful and there is no detail that hasn't been addressed. The food is amazing - the breakfasts are divine and the afternoon cheese and wine tray with those cookies are nice treat to enjoy after a day of exploring Galena! Would recommend a stay here with a most gracious host! read more

We were absolutely thrilled with our stay at the Jail Hill Inn. The breakfast was extraordinary as well as the 4pm appetizer tray accompanied with a bottle of wine. Our innkeeper, Matthew Carroll's, attention to detail made this the best B&B stay that we have ever had. We highly recommend it. read more

Spectacular stay! You won't be disappointed. My husband wanted to surprise me with a weekend get away with golf and bed breakfast stay. Upon our arrival, it was more than I could image. The Jail Hill Inn was so beautiful. The Innkeeper Matthew was extremely hospitable and accommodating . Our room had pipe music, bathroom was gorgeous and breakfast so delicious! I highly recommend staying at the Inn. I can't help telling everyone I know. It was the best weekend vacation ever. My husband and I will definitely be return visitors. Thank - you so much, Matthew. You are a true blessing in your craft. See you soon on our next visit. read more

A perfect romantic getaway. The entire weekend my wife and I could not stop talking about how charming and relaxing our room was. Matthew, the Innkeeper, seems to have thought of everything when it comes to comfort and relaxation. Our brunch each morning was healthy, fresh, and gourmet prepared. There was complimentary wine and finger foods in the downstairs shared sitting area each late afternoon and evening. Matthew was always attentive, warm, and welcoming with any requests. We loved that we were steps away from the main shopping street of the town, and walking distance from historical sites to tour and the charming businesses of the town. We plan on returning to The Jail Hill Inn and becoming "repeat offenders" as we loved staying in our room so much this past weekend we still have so much of Galena to see. read more

I can not even put into words how incredible this place is. We were looking for an upscale B&B that didn't feel like grandmas house and this place is perfection. My husband and I booked a weekend here for our anniversary and are beyond impressed! We're staying in suite 201, the old Sheriff's suite, and it is so luxurious, beautiful and comfy. The inn keeper/owner Mathew didn't miss a detail down the bathrobes. Love it! Hospitality & customer service is superb and food is fantastic! Already made my husband promise we'd come back here again one day. :) Looking for a romantic get away? Come here! You will not regret it! read more

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The Jail Hill Inn is a perfect couples get away! The breakfast is always delicious, three courses! The rooms are all unique and gorgeous! Downtown is a short walk away!! Matthew is a terrific host!! read more

Perfect. Everything. The room, the food, and especially the service from Matthew! One of the few places that should get six stars.

My husband and I spent two nights in suite 201. This place is everything it claims to be and more! Our suite was so spacious and the Bluetooth speakers throughout were a great touch. The breakfasts were fantastic, though don't plan on eating lunch any time soon afterward because they are filling! I loved the wine and snack tray that came by in the evening as well. Matthew was a great host and very willing to help with making plans. The location was perfect and worked out great for walking downtown. We never got in our car between the time we arrived and the time we left to go home. We will absolutely be back and look forward to trying out other suite! read more

Jail Hill Inn - Evening cocktail hour! - Bed & Breakfast Near Me - Galena, Illinois

This place has all the charm of a bed and breakfast but with the service and quality of a Four Seasons resort! The location of the property is right off main street which we love. We were able to park the car, walk to all the great stores and the stumble back from a must visit of Jamie's Wine Studio of Galena! There is nothing in the area that can compete with the luxury and service level at this Inn. read more

Jail Hill Inn - Bed & Breakfast Near Me - Galena, Illinois

Top notch in every way. Matthew the innkeeper puts everything together to make his small hotel perfect!

Matthew never disappoints. The rooms, the breakfasts, the happy hours and the service are all top notch. This was our second stay and we are already planning our third! read more

ALL IN THE DETAILS! From the historic architecture to the modern conveniences, everything was brought together by Mathews incredible attention to detail. The great location also made it easy to walk to all downtown sites. I've stayed at many bnb's in Galena the last 10 years and this one stands above all others. Looking forward to returning! read more

My wife and I stayed at the Jail Hill Inn this past weekend. The restoration of the building is beautiful. Matthew is a fantastic host and makes you feel like a guest in his home. The king size bed is great but the sheets are amazing. The softest I have ever slept on. We asked about them and Matthew volunteered to order a set from the manufacturer and have them drop shipped to our house. The suites are very large and comfortable. The bathroom is spa like with a jetted tub and seperate shower. The breakfast is amazing!! The 3 course breakfast is the best I've ever had! There is also a wine/cheese/fruit serving at 5pm that is a perfect start to the evening. The complementary bottle of champagne upon your arrival is a nice touch also. We truly enjoyed our weekend and look forward to going back in the fall. read more

This B&B is spectacular -- the best I've every stayed in, anywhere, and I'm picky. I love the small, unique feel of a B&B, but it's so hard to find one that doesn't make you feel like you're sleeping in grandma's bedroom. Not here! Each room is unique, and modern without being sterile. We were in 201, which has the feel of a rustic loft feel, but the innkeeper, Matthew, showed us the other rooms (we were early and the first guests) and they were all lovely. They were also spacious, with separate living rooms and kitchenettes -- it's like being in an apartment. A bottle of free champagne was waiting in our room when we arrived, and free wine and hors d'oeuvres were waiting for us around 4 in the lobby each evening. Matthew also kindly let us buy wine from him at a fairly reasonable price and delivered it to our room upon request. And breakfast was great -- three courses. I ate better at Jail Hill Inn that I did anywhere else in Galena. I told Matthew he should open a restaurant next. Matthew's story is also amazing. He used to manage the only other B&B in Galena we considered, then bought and renovated this old jail. And he runs it only with the help of his parents and a local high school student. So much sweat and money and love clearly went into it; staying there, you can't help but feel honored to be part of it. read more

Jail Hill is the best Bed and Breakfast not only in Galena, but out of all of them I have been to! It's my third time and counting coming back to the Jail Hill. Matthew provides the best hospitality with a smile on his face and truly makes you feel like family there. It's conveniently located in downtown Galena. Can't say enough great about this place, we will be back! read more

My husband and I recently stayed three nights in room 401 and I cannot express enough how much this B&B exceeded our expectations. What Matthew has created here is not only a restful escape and a fun adventure, he wraps it all up in a piece of timeless history within the original Galena Jailhouse. The breakfast is easily the best I've ever had, utilizing many of the fresh ingredients from his parents own garden, as well as nearby farms. The modern amenities, including in room blue-tooth sound system, jet tub, and shower area with seating and multiple shower heads (just to name a few), do not at all take away from the feeling that you are staying in a building that has stood the test of time. Matthew's thoughtfulness and dedication to what he has created here shows in every detail of your stay. The décor, the main lounge with fireplace, the rooms, the breakfast, the afternoon hors d'oeuvres, the outdoor patio and secluded back deck, are all very comfortable, warm, and welcoming as well as so opulent you will know you are staying somewhere truly special and unique. We can't wait to go back and try more rooms! Paul and Jennifer Naylor, Chicago, IL. read more

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Jail hill inn This new addition to the Galena bed and breakfast scene has certainly set the bar high. This six suite boutique B&B will leave you awe struck in its classic styling with an eclectic mix of everything good of both the old and new. It is hard to believe that such an exquisite property was once an actual jail. However, the subtle nuances of this have been tastefully embraced by The Jail Hill Inn's proprietor, Matthew. While each suite is equally worthy of a five star rating, Matthew managed to maintain the rich history of the property through subtle details, such as exposed beams and brick in the ceilings original to the building when it was used as a jail. But make no mistake, this bed and breakfast is nothing less than perfect. Besides the grand decor, every amenity a guest could want has certainly been thought about and delivered. From integrative blue tooth surround in every room, luxurious beds, linens, fine Turkish towels and robes, champagne and chocolates upon check-in, to the nightly wine and appetizer reception and three course gourmet breakfast, the Jail Hill Inn certainly leaves no detail forgotten. ( I have to pause here to comment specifically on the delicious bacon chocolate chip cookies, banana, chocolate, poppy seed muffins and vegetable strata with roasted potatoes and twisted maple bacon). I cannot say enough about our gracious host, Matthew, who left us not only loving the Jail Hill Inn, but who also set the stage for a continued appreciation for the town of Galena. We will definitely be back! read more

My wife and I loved this place! Everything is done top notch....from decor to service. The attention to detail is the best I've seen. If you don't stay here you're making a huge mistake. Matt, the owner, was extraordinarily gracious. I couldn't find one thing wrong with the room or the property. We were sad to leave. Our stay here just enhanced our trip to Galena and made it priceless. read more

We came here for a romantic weekend away for New Years. To say Jail Hill Inn in is amazing is an understatement. It is out of this world. All the reviews are correct in giving it 5 stars. If there was an option to give more, I would. Matthew is amazing & he cooks the best food. We told him we are Vegan & he adjusted the menu & served us food that we couldn't even find at a Vegan high end restaurant. He makes the most beautiful & delicious meals. The place is beautiful. The rooms are like small apartments. We wanted to move in. The sheets amazing. The tub fits two people perfect & it is so relaxing and amazing. Fireplace is a beautiful touch. It was decorated for Christmas. So magical. You can walk to all restaurants & shopping. It's in the perfect location. We did not need the car the entire time we stayed there. If you want the best service, food, atmosphere, romance & everything else that is amazing - you have to stay here. We are coming back for sure. My fiancé wants to write his own review on this because he loved it so much! Thank you Matthew! You made our weekend & a great way to start 2017! read more

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Jail Hill Inn is hands down the BEST B&B in Galena. The luxury and attention to detail are unparalleled. Each room is spacious with and cozy with designer touches and historical details. We loved the original brick ceilings, spa tub, fireplace, and 9 ft windows bringing in gorgeous light. Matt has thought of everything and no expense was spared in making this a five star experience. There are handmade local chocolates and a bottle of champagne in the room upon arrival, a wine and cheese reception with delicious appetizers, Bluetooth speakers in all rooms, spa quality sheets and robes... the list goes on and on! The breakfast was exquisite. Matt is a wonderful host, offering luxury with a humble, down-to-earth personality. We loved chatting with him. We will definitely be back. I honestly would not consider staying anywhere else in Galena. Do yourself a favor and stay at Jail Hill Inn! read more

This bed and breakfast is just unbelievably nice. Located about one block from the downtown mainstreet, this is very convenient to stay here and enjoy all that downtown Galena has to offer. This is a converted 19th. century jailhouse. Matthew, the proprieter, has turned it into an exquisite 6 suite bed and breakfast. Matthew is the nicest young man and I can tell he works extremely hard. He has thought of everything. Late afternoon, he has a nice spread of cheese, fruit, crackers, and wine to enjoy. Our suite (they all are about 800 sq. ft.) featured a fireplace, a sitting area with refrig and coffee maker, and a very nice bathroom with steam shower and the softest robes you will ever find. Our suite also featured a backdoor leading to a large deck for the guests. The suite also featured a sound system you could use to listen to the smooth jazz channel or hook your own device up via blue tooth to listen to your own music. One last feature of our suite was an original piece of wood in the window that had names, carved into the wood, by prisoners that stayed there over 100 years ago. The bedding features the softest sheets I have ever slept on. The breakfasts are unbelievably good and LARGE!! You will not need lunch and may not need dinner. The presentation rivals any chef anywhere. All in all just an exquisite experience. And if you don't leave feeling you have a new friend in Matthew, something is wrong with you. Jail Hill Inn gets my wife's and my highest recommendation and we booked another stay in 2 months. This was one of the nicest and most relaxing weekends we have had in a long time. Thank you, Matthew! read more

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This was by far one of the nicest B&Bs we have ever stayed in. Matt the owner is so nice and accommodating. The Inn is spectacular. Clean, fresh, new!! The attention to detail is phenomenal. What a perfect way for my husband and I to spend time together and celebrate my birthday. Highly recommend this beautiful B&B!! Thank you Matt! Great job!! read more

How can I even begin to express my feelings about Jail Hill Inn? If you want an eloquent Bed & Breakfast that is like none other we have ever experienced look no further. From the moment you walk in the front door you are greeted by the owner, Matthew Carroll, so warmly you feel like you have known him forever. A wonderful array of appetizers awaits you as he explains everything that awaits you on your stay here. Matthew accompanied us to our room and all I can say is Wow. The room is so inviting you truly don't know where to look first. The decor is stylish and so refreshing you never want to leave your room. There are fresh flowers, complimentary champagne, chocolates and anything else you could ask for at your disposal. This isn't Grandma's house for sure. Top notch Bluetooth, state of the art TV and anything else that the 21st century has to offer, Matthew has incorporated it into his establishment. The bedding is dreamy, you are engulfed in its comfort for a wonderful nights rest. The bathroom is beyond description. A breakfast awaits you in a gorgeous dining room after your nights stay. I could go on and on but as you can tell this is a top notch Bed & Breakfast-don't miss a stay at Jail Hill Inn if you are visiting Galena, Illinois read more

We just stayed at the Jail Hill Inn for an anniversary getaway and were blown away by our visit. We stay at a lot of B&Bs and have recently started looking to stay exclusively at Select Registry sites because of the guaranteed high standard. Jail Hill Inn is probably the best B&B we have ever stayed in. The rooms are gorgeous. They are huge and uniquely decorated (we snuck a peek at other rooms on our way out and each one was decorated differently from the next). The attention to detail in the room finishes is outstanding. Matthew, the innkeeper, has done a phenomenal job blending his experience from managing the Irish Hollow into a venture of his own. He earned a well deserved preservation award for bringing the Jail back to life. While maintaining wonderful pieces of the building's character, Matthew has managed to weave in all the modern comforts expected of a B&B of this high caliber. Matthew's food is also fantastic. We are nearly always underwhelmed by food in the Midwest outside Chicago, but this was not the case at all with Matthew's breakfast. His ingredients come from his parents' garden and the use of organic produce, spices and quality ingredients is evident. We've been spoiled now and will have a hard time being satisfied elsewhere! read more

Believe it. Every 5 star review is 100% correct. The attention to detail is astounding, the food is amazing, the beds are heavenly, the whole place is divine. Book it now because there is going to be a waiting list to get a room. It really is that good. read more