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Kentucky’s Over-the-Top Overnights

In Kentucky, your group’s overnight accommodations might just be one of the trip highlights.

Around the Bluegrass State, unique hotels and other accommodations infuse Southern hospitality with Kentucky history, signature elegance and elements of whimsy. Consider some of these one-of-a-kind properties on your group’s next tour through the state.

Kentucky Castle


A boutique hotel experience like no other can be found within the stone walls of a medieval-European-style castle in the heart of the Bluegrass. Despite its vintage look, the Kentucky Castle, also known as the Martin Castle, has only been around since 1969. That’s when the Martins, a husband and wife inspired by the European architecture they’d seen on their travels, began construction on what would become a beloved central Kentucky landmark. It’s now a boutique hotel with 18 overnight accommodations, an upscale restaurant, a working farm and event venue. The restaurant features farm-to-table fare and a wide selection of wine and bourbon. The property also has a pool and a spa and offers experiences such as bourbon tastings. Its rooms range from turret suites to a cabin; since space is limited, reservations need to be made well in advance.

The Manchester


Lexington’s newest boutique hotel takes the form of a chic brick building rising seven stories above the Distillery District. This rustic and revitalized district includes a Goodfella’s Pizzeria, craft ice cream shop Crank and Boom, the historic James E. Pepper Distillery, several breweries and cideries, and now, a 125-room hotel. The Manchester, decked in rich hues of navy and green, as well as wood, leather and brass, is an elegant tribute to the Bluegrass. From horseshoes to bourbon barrels, the hotel’s luxurious finishes and small touches pay homage to the region’s major industries. Granddam, the hotel’s restaurant, creatively reworks Kentucky and Appalachian staples into fresh, upscale meals for breakfast, lunch and dinner. The hotel’s rooftop bar, Lost Palm, incorporates a Floridian feel with art deco finishes and impressive cocktails.

Wigwam Village No. 2

Cave City

Groups looking for a less traditional hotel stay can enjoy the rare experience of sleeping in a “wigwam.” Wigwam Village No. 2, one of seven villages created in the 1930s by a Kentucky businessman, consists of 15 unusual structures — and these structures more closely resemble teepees rather than wigwams. The steel-and-wood framed teepees are covered in stucco, and are much larger than actual teepees, as they either sleep two or four guests, and each has its own bathroom. All feature original hickory furniture. What the village lacks in cultural authenticity, it makes up for in kitschy roadside Americana charm. It’s on the National Register of Historic Places and can be appreciated as something of a time capsule to the 1930s. The village is found in Cave City, near Mammoth Cave National Park, which attracts half a million visitors annually.

Historic Boone Tavern


Built to accommodate guests of Berea College, Historic Boone Tavern is a hotel and restaurant constructed in 1909. The sprawling white building with stately columns was designed in the Colonial Revival style and constructed using bricks from Berea College’s brickyard. It underwent a $9.6 million renovation in 2008 to add guest rooms and improve energy efficiency while preserving its historic charm. Decorated in rich shades of blue and warm wood tones, the 63-room hotel is known for its character and attentive service. It has hosted guests such as the Dalai Lama, Eleanor Roosevelt and Robert Frost. The hotel’s restaurant is known for serving spoonbread and other Southern cuisine, including its signature dish: chicken flakes in a bird’s nest.

The Brown Hotel


One of the most iconic Kentucky foods, the hot brown, is an open-faced sandwich comprising turkey, bacon and tomato and smothered with cheese sauce. It was first served at Louisville’s Brown Hotel, where it got its name. Celebrating its centennial in 2023, the Brown Hotel is a luxurious and richly decorated historic hotel in downtown. With grand chandeliers, glimmering ceiling decals and stately arches, this quintessentially Kentucky hotel is a classic stay for groups. It has 294 rooms and suites with mahogany furnishings and rich upholstery. J. Graham’s Café has light fare a la carte for guests to dig into, while the Lobby Bar and Grill is open for dinner and offers both extravagant cuisine such as sea scallops and filet mignon, as well as staples like smoky macaroni and cheese, the hot brown and derby pie.

Benham Schoolhouse Inn


Located in Harlan County, surrounded by mountains near the Kentucky-Virginia border, Benham was founded as a coal mining company town in 1911 by Wisconsin Steel. These company towns were self-contained and encouraged miners to raise their families in the town by providing a company store, school and hospital. The Behnam Schoolhouse Inn was built as a school in 1926. It was converted to an inn in 1994 and is one of the state’s most authentic stays for those interested in learning about Appalachian and mining history. Each of its 29 rooms is distinctly decorated, and many still feature the original hardwood floors. The Dinner Bucket, the inn’s restaurant, is located in the school’s former offices, while the gymnasium was converted into an elegant banquet hall. Lockers, complete with love notes and other tokens from former students, still line the hallways.