Landon Hill Bed & Breakfast - Bed & breakfast in Chestertown - 10 Landon Hill Rd, USA

This was our first time staying at a Bed and Breakfast and my fiancee and I had a fabulous time. Carl and Judy are the hosts and they are both so sweet and VERY hospitable. The house is well kept- clean and so quaint and cute. The house is also large and there is plenty of space. We booked late and got the smallest room with a bathroom in the hallway and it was still a great stay. Our room had a alarge bed, plenty of space and the bathroom was clean. I did see all the rooms before leaving and they are superb. They have redone all the bathrooms so they are beautiful and clean. So the stay was definately comfortable. Next- the FOOD!!! judy is a great cook, she makes you delicious breakfasts in the morning and their coffee is so good! We had a wonderful weekend. Its about 25min drive from all the touristy stuff, but we still managed to go rafting and biking without any problem. I would definately stay here again!|

I originally chose Landon hill because of the reviews. I have to say I had a very different experience. To start, we were originally promised the Trillium room for $140. When it came to actually putting down our payment, we ended up with the Northface room. Judy the owner said the Trillium Room cost more. Sticking to our original budget, we took the Northface room. The pictures on their site looked decent. Upon arrival, Judy was very kind to leave us a note and the keys. When I went to look at the room, it looked nothing like the photos online. What was supposed to be a KING size bed, was actually 2 twin size beds pushed together. Which I could have dealt with but they should have been honest. Secondly, the room was not only really small there were cracks all over the room. There were water stains under the air conditioner and the bathroom was not a real full bathroom. I called Judy to tell her my dismay in the condition of the room and instead of trying to switch me to another room, she was offended and dismayed. We both decided that it was best that my boyfriend and I didn't stay. I went down the road and found a B&B for $19 more that was in much better condition. I did receive a refund in the mail right away. Which I highly appreciate. Judy did apologize for her directness but the letter also said if i wanted a cheaper room, I should stay in a motel next time. Little did she know, I paid more for a nicer room and experience. I wouldn't say not to stay here, but for the price, you can definitely do a little better. Maybe the other rooms in the house were in better condition. I would just say, know what you are getting into.

My wife and I, along with several friends were going to be in the area for a wedding. We chose to stay at the Landon Hill B and B. I am glad we did. The owners were engaging and pleasant. The bedrooms and bathrooms were clean and comfortable. The grounds were interesting and we spent a very happy hour sitting in adirondack chairs and enjoying the view. We also stayed up in the sitting room for a late night conversation with the group. My only complaints may be things that cannot be corrected. The television reception is poor and the advertised free Wi-fi was not strong enough for my iPad to lock onto. Maybe that was for the best, in the opinion of my wife. ||Breakfast was plentiful around the dining room table where we lingered until almost the 11 AM checkout. It is very convenient to I 87 and to Chestertown shops etc. but when at the B and B, you wouldn't know it. I would stay here again.

My wife needed a room for one night with almost no notice. We scrambled and called some B&Bs in the area. I suppose they were full or just not too motivated because I didnt hear back from 2 of the 3, Judy from Landon Hill rang me back and said she had a room but that she was out getting ice cream so she couldn't take my name or credit card. I thought it was very quaint that she eimply trusted I would show up, and that i would just pay her whenever I got there. And when we arrived she was just a doll, she presented 5 good choices for dinner and we opted for OP Fredricks and it was awesome (Judy recommended the Duck Burrito - weird- but great). The room was clean and neat and well appointed, I've been to B&Bs from Cape Cod to Maryland and this one was very nice. Large common room, nice size dining room and central location. Our room had a large bathroom and plkenty of windows. We liked it a lot. Thanks Carl and Judy for sharing your home with us.

Lovely place, well appointed and cared for. Ours was an odd group, here for 2 nights for a special event, then back home (curse you, covid19), thus we were home bodies rather than doing local activities. Hosts were great. We arrived early and things weren't quite ready, but they saw to our needs. They were friendly, gave good directions as needed, steered us to the local lunch cafe / ice cream parlor, which was excellent. They checked on us a few times then left us to enjoy there place. Excellent location right on the edge of town - a pleasant 5 min walk, if you don't want to deal with car issues. The town (village) is lovely, tiny, quaint (sorry, I grew up in Brooklyn - anything under 100,000 is quaint), but has what you need and a few nice, if boutique-y, shops. Less that 20 minutes to summer and winter activities (and Saratoga; worth a visit). Easily managed our group of 13 folks: bathrooms, lounge areas, dining, grill setup, comfy bedrooms, AC (yes, a given, but you'd complain if there were a problem), good wifi, TV okay ( except one BR), fire pits (and good wood). All round, a good time.

This was the 5th B&B I've stayed in, and it was by far the worst. I told Judy I was traveling for my fiancés 30th birthday, and asked if she could have something special waiting. We walked in and she was in the kitchen making cookies- so I thought that was the "special surprise". I could not have been more wrong. The only surprise I encountered was an old, dingy room with NO air circulation, a tiny shower and bathroom (that was in the main hallway), and two twin beds pushed together to form a King bed (that had elevated padding in the middle to prevent you from falling between the two beds and PREVENT any sleep). I was hoping for maybe a balloon or some flowers - wrong. I never saw the cookies, or anything special. Furthermore, the breakfast consisted of French Toast, bacon, and grapes. What happened to a choice? ||||I did walk by other rooms and they looked MUCH nicer than ours, so maybe that was the big turn off. Judy told me she would upgrade me to a better room if there were any open, and there was, but the upgrade never happened. The B&B was centrally located which was nice, but that was the only positive thing about this place. ||||I would ONLY recommend this place to someone that gets the Northface room. There are much better options out there! Beware!

We stayed one night at this lovely B&B for a wedding we were attending this past September. Carl & Judy were very friendly and accommodating--made us feel very at home from the get go. They honored our reservation with a 3-year-old and also rearranged a double ito a King so that the 3 of us could sleep comfortably together at no extra cost. I would definitely recommend this place if you are in that area.

We have stayed and Landon Hill four times. It provides easy access to our son's camp when we go to visit. While it is by no means elegant, it is clean and comfortable. Judy is warm and welcoming and it feels like you are at home. Life and the inn is simple and relaxed. Which makes the entire experience pleasant. If you are looking for fancy, you can find it, but you will pay more for it and miss out on simply feeling welcomed into someone's home.