A Repeat Stay at the Best Western in Winchester, KY Delivers

Years ago, my mother and I stayed at the Best Western Hotel in Winchester, Kentucky, when we attended the Homer Ledford Dulcimer Festival. The festival doesn’t happen anymore. Ledford, a prominent instrument maker, including the mountain dulcimer, was a well-known Bluegrass musician. He is one of Winchester’s favored sons. 

I remember my mom sitting on one of the beds in our hotel roo,m putting tiny numbers along the neck of the dulcimer that she lent me. Because I had no idea how to play a dulcimer, the numbers helped with finger placement. Despite taking more lessons, I still don’t know how to play much more than “Boil ‘Em Cabbage Down.” Still, I have a wonderful memory of this Best Western stay with my mother.

Best Western in Winchester, Kentucky

New Memories at this Best Western

I recently gained another wonderful memory of this hotel. A few months ago, when my husband, son, and I pulled into the hotel parking lot, I had a flashback to that earlier time. “I think I stayed here before,” I said. It is not that unusual that we would end up here because Winchester does not have many hotel options, particularly within walking distance of downtown. The Best Western has high ratings.

This time we came for an aunt’s birthday party and the Daniel Boone Festival. Although the hotel has been updated, I remembered the layout. Guest rooms are over two floors with all rooms opening to the outside. A parking lot is between the buildings that include an office building and a separate space for tobacco smokers to puff away.

Smoking area Best Western, Winchester, KY

This layout is an old-school road trip hotel format. It’s my favorite format because it makes unpacking and packing a car easy. There is no need to pile belongings on a cart to bump along a hallway, up an elevator, and down another hallway. Of course, we did have to lug a bit because we were on the second floor. 

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Mural of Daniel Boone, Winchester, KentuckyThe hotel delivered just what we needed between my aunt’s party at night and the Daniel Boone festivities in Winchester’s downtown the next day. Because our daughter and 7-year-old grandson were on this trip with us, we wanted a clean, comfortable hotel with two adjoining rooms. My daughter and grandson checked in first. This was a slight problem because the hotel system was down. This meant it took them longer to get the key to their room. By the time we arrived, the problem was solved. This was the only hiccup. 

The Rooms

Our two queen beds room was what I had hoped it would be. The bedding is updated to modern taste. Gone are the bedspreads from years ago. Instead, the soft, white bedspread comforters give a clean, crisper look and feel. Bedside and table lamps are also sleeker with simple white, modern-style shades. The carpet is also updated as is the art on the walls, the desk chair, and the light wood furnishings. All are modern and simple. Nothing is worn and tired-looking. 

Best Western Hotel Winchester, KY two queen room

There is also a large flat-screen TV on the long dresser. Other furniture includes a desk with a modern office-style chair and a large, comfy armchair. There are plenty of plugs for electronics. The lighting above the long vanity sink has also been updated to a modern look. Because the vanity sink is separate from the bathroom, this was great for the three of us. My husband, college-age son, and I shared the space. Like the rest of the room, the bathroom with its tub with a shower was clean and in good shape. The alcove space with a clothing rack next to the sink is a place to tuck away suitcases and other belongings.

Other room amenities include a microwave, iron, ironing board, refrigerator, coffee maker, and ice bucket. Quality shampoo, conditioner, and body wash are in wall dispensers in the shower. Our daughter’s adjoining king room was similarly appointed. 

The Rest of the Best Western 

Best Western Lobby, Winchester, KY

The lobby has drinks and snacks for purchase

The lobby with the check-in counter and breakfast area are in a separate building across the parking lot from the main hotel. There is a throwback to an earlier time feel here, but that is part of the charm. The tile floors are new from when I stayed before. So are the furnishings and the counter where breakfast is a help yourself version. The chairs with their fabric-covered backs and vinyl seats seem from an earlier era, but they are in excellent shape. 

The breakfast area of the Best Western, Winchester, Kentucky

We hung out here a bit, talking to guests who are distance motorcycle riders. Although we arrived a little late for breakfast, we were able to snag the last of the biscuits and gravy, scrambled eggs, and crisp bacon. Yogurt, fresh fruit, several cold cereal options, and a variety of breads are also included in the mix. 

Although there is an outdoor swimming pool accessible from the hotel’s 2nd floor, and it was blazing hot, we didn’t swim. We were off to the Daniel Boone Festival. The pool does have seating and some shade.

About the Daniel Boone Festival and Winchester, Kentucky

Winchester, Kentucky’s downtown, is splendid. Established in 1793, this small city is southeast of Lexington and considered a “Gateway to the Mountains” of Eastern Kentucky. Natural Bridge State Park is close by. Downtown, you’ll find more than 100 historic buildings with Victorian and Federal architecture, which has placed the district on the National Register of Historic Places. Each building is as stunning as the other.

Daniel Boone Festival Winchester, Kentucky

Daniel Boone Festival in the historic district of Winchester, KY

These days, the buildings have a mix of boutique shops, a distillery, and restaurants. The Daniel Boone Festival goes the length of Main Street with entertainment stages set up at various locations. A variety of craft and food booths fit every style and budget. The festival is named for Daniel Boone, the frontiersman, and pioneer who blazed a trail through Kentucky’s wilderness to help with westward expansion, who lived in these parts. Just minutes from Winchester, Fort Boonesborough State Park has a replica of the fort where Daniel Boone lived and is well worth the visit. 

We booked our rooms at Best Western Winchester through the hotel’s website because my daughter qualified for a military discount. Room rates currently start at $92.99. For a stay with access to all this part of Kentucky offers, I do recommend this hotel as a place to consider. 

Check rates online at Expedia, Booking.com, or Hotels.com.

Post and photos by Jamie Rhein

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