We had a wonderful stay at Cumberland Manor. The hosts were wonderful and Jill was a font of information about things we shouldn't miss in Cumberland Gap Park. Our bed and room, the Washington room, were very comfortable. The breakfast was outstanding. The porch was a great place to sit in the evening and drink a beer. Our only regret is that we didn't know how much we'd enjoy our stay in Middlesboro and we'd only planned for a one night stay ... don't make this same mistake while planning your visit. read more

Great Bed n Breakfast! The owners Jill and John are great hosts and the breakfasts are awesome. The House is so interesting and the room's are comfortable with nice soft sheets. John has added amazing woodwork to bring the house back to the era when it wss built. You will not be disappointed with this choice. Jill also spends time in the morning giving a brief summary of what you should do while visiting. Thank you for your awesome hospitality. We hope we are back in the area some day. read more

We visited at the end of August 2013. Jill (our hostess) made sure we felt right at home. She always made sure we know where coffee or muffins were, she made us delicious breakfasts, told us about Middlesboro history, and generally made us feel very welcome. We stayed at the blue room in the attic (Kennedy Room) and loved its size, feel, brightness. There is this cute little black and white doggy that lives in a house next door, and it follows you when you go for a walk. :) Great place to visit! read more

A great B&B. Good host, great house in a great location in town. Lots of common sitting space, front porch space, and plenty of parking. We stayed in the Roosevelt room, a more or less standard B&B room. The Lincoln room is a suite. Highly recommend. read more

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Talk about historical charm! This three story Manor is stunning, and so well decorated. Lots of seating areas down starts. Jill is a wonderful cook, and she is so knowledgeable about her home, as well as the surrounding area. I would go again in a heart beat. It's so close to down town, but you would never know it. It's up on hill, and has some nice views of the city/mountains. The home was originally built in late 1800s in the center of a meteorite crater. There are sitting spots outside on the porch, or in the garden. Jill has a wonderful way of making you feel like family. read more

Jill is the most gracious host you'll find anywhere and the mansion is absolutely gorgeous! Jill cooks an amazing breakfast and you won't regret staying at the Cumberland Manor B&B one bit. The home was built in the late 1890s but is extremely comfortable and all her furniture is antique so it really feels like you're stepping back in time. Jill does a great job decorating as well and is extremely courteous in accommodating your needs. Wifi is included and extremely fast so you'll have no problem staying connected. They also have a parking driveway that has room for 7-8 cars. Whether you're in town for business, pleasure, or just passing through, a stay at the Cumberland Manor is a must! read more

We stayed at Cumberland Manor during my nephews graduation from nearby LMU. We thoroughly enjoyed our stay. The home was absolutely beautiful, filled with antiques that the owners, Jill and John had collected over the years. Jill was able to tell us fascinating stories about the town of Middlesboro (the only town in the US built into a crater if I remember correctly). The breakfasts that Jill prepared for us were excellent- frittatas, blueberry muffins, cinnamon bread pastry, toast with homemade blueberry moonshine jelly...! Jill went out of her way to make us feel welcome and comfortable. She even invited us to sit with she and her husband around a campfire that they had built in. the back yard. we will definitely try to return to Cumberland Manor in the future. read more

I stayed at the Cumberland Manor B & B this past January and had a great experience. The owners are very, very nice and accommodating. The house itself was one of the first houses in Kentucky to get electricity and they have refurbished the common area and bedrooms extensively. Jill is also a great cook, so there's a whole lot to like about this B & B! read more

Jill is a gracious host who provides a delicious breakfast of both the sweet and savory varieties which we enjoyed during our two-night stay. This old home dates back to the 1890s, but is extremely comfortable and provides a "step-back-in-time" experience with the antique furnishings. Free wifi provides the opportunity to easily stay connected. Jill is very knowledgeable about the area and was able to provided suggestions of places to visit and dine during our stay which was most helpful. If you are in the area, Cumberland Manor B&B is definitely the place you want to stay. read more

My husbands family visited the area for the first time ever and Jill made their stay the absolute best! We were served an excellent dinner and breakfast; wow can she and John cook some amazing dishes. I simply could not pick a favorite; the smoked pork roast, roasted seasonal vegetables, pumpkin bars, French toast casserole, and cooked apples with cranberries are some of the best dishes I have been served! The house is beautiful and the porch was so perfect for the families to spend time together. Jill took excellent care of everyone. Even addressing special food needs. Definitely the best accommodations and hospitality in the area! read more

A gorgeous old house lovingly restored by the owner, John to its 1890's glory, but with added disabled access, and central air. Like stepping back in time and being a guest in a great Victorian manor house. The bed (king room) was very comfortable, and we slept well. The owners were very accommodating in letting us arrive late at night, and even plugged in my car to charge. Possibly the worlds greatest omelette for breakfast, home made by Jill, who is a great chef. Unfortunately, the lovely large bath had been broken by previous guests, and we happened to stay between then and the replacement parts arriving. The curtains did not make the room very dark, so if you are bothered by the light and want to sleep late, bring a mask. I'd absolutely go back, and recommend. read more

We thoroughly enjoyed our three-night stay at the Cumberland Manor B & B in Middlesboro. Our hosts Jill and John have done a wonderful job of restoring the historic Victorian home to its original 1890's grandeur, and Jill has beautifully decorated the inn with her large antique collection and many other creative touches. We were at the inn in the fall, and the house was full of festive fall arrangements. The large front porch was also adorned with fall decor and had many comfortable chairs where guests could sit and enjoy the distant mountain views. Jill's breakfasts were delicious and very filling. She adds unique personal touches to all of her breakfast offerings--things like a warm mixed fruit compote for French toast, fresh veggies from her garden in a frittata, and tasty herbs in her eggs Benedict. We enjoyed getting to know Jill and appreciated her willingness to spend time explaining local attractions, describing hikes she had taken herself and recommended for us, and telling us about the history of Middlesboro and the inn. We felt like we were leaving a friend behind when we said good bye to Jill and went on with our travels. Mike and Christy read more

We enjoyed our stay at the Cumberland Manor B&B! Jill, our hostess, made us feel like old friends. She graciously accepted our last minute request for a room, which I am ashamed to admit was poor manners on my part. The Manor was decorated in wonderful antiques that complimented the Victorian style of the home. It was very clean and comfortable. Due to the government shut-down of the federal parks we had to make new plans for our visit to the area. Jill provided us with numerous enjoyable options, so that we didn't even miss our original plans. She provided wonderful full breakfasts of tasty homemade (and grown) delicacies. We would highly recommend Cumberland Manor B&B and our hostess, Jill. read more

I thoroughly enjoyed my stay at Cumberland Manor last week. Jill was an amazing host who made me and my colleagues feel right at home with her warm personality. Jill made sure we had everything we needed and gave us lots of great insight about the area. Her breakfasts were beyond incredible and I will be dreaming of them for many nights to come. The manor is a charming house with very neat decór, I particularly liked the giant world map covering the wall on the second floor. read more