Boutiques of the Bluegrass

The Bluegrass Region has long been synonymous with hospitality and the ability to provide overnight guests not just a soft bed, but a slice of commonwealth history with that bed. Think Boone Tavern in Berea, and Mercer County's Beaumont Inn and the Trustees' House at Shaker Village.

These historic havens are still in high demand, but today they are joined by an influx of newer properties (many in repurposed historic buildings) competing for tourist stays.

The Manchester

Lexington, Fayette County

When guests turn the key to a room at this luxury Lexington property, they are doing it with the blessing of the MICHELIN Guide.

For the second year in a row, The Manchester has been given the coveted One MICHELIN Key, the hotel counterpart of a restaurant star.

The only Kentucky hotel to receive this distinction, the Key indicates "a very special stay."

A special stay is just what you'll get at this 124-room independently owned property which according to the Guide, "distils the quintessential Kentucky high life into one mid-century maximalist property."

It goes on to describe the warmth of the public spaces, courtesy of the stained wood, leather and brass in the decorative touches, and to praise the carefully chosen textiles in all the guest rooms.

Dining at The Manchester is a major selling point – whether you reserve a table (and you must) at the Granddam, to enjoy chef Paula Endara's elevated take on Appalachian cooking – think country ham and leek chowder and Lamb Wellington with locally foraged mushrooms, or the more casual rooftop bar, Lost Palm, offering tropical cocktails, a raw bar and panoramic views of downtown Lexington.

Insider tip: If you want to look like a local, know that in Thoroughbred horse lingo, a Granddam is a grandmother horse. Casually throw that out and your server will be impressed.

You are the one who will be impressed with The Manchester's great location, anchoring the Distillery District, a popular entertainment area, and just across from Gatton Park, an urban oasis.

Historical connection: The hotel may be new(ish), having opened in 2023, but it occupies the former site of the Ashland Distillery, Lexington's first federally registered bourbon producer, established in 1865.

The Delegate

Frankfort, Franklin County

Until recently, Kentucky's capital city was something of a hotel wasteland. All of that changed in 2024 when Common Bond Hotel Collection out of Louisville introduced not one, but two boutique properties within months of each other.

The first, the 48-room Delegate opened in October of 2024, combining timeless tradition with contemporary cool.

The timeless tradition part involved the meticulous restoration of an 1879 three-story Italianate building that originally housed the Jeremiah Weldon South Warehouse, which at one time even served as a factory storing millions of pearl buttons.

Traditional meant retaining original features such as exposed brick walls, wood ceiling structure and original windows – complementing them with custom lighting, new wood floors and artisan furniture.

The cool factor came courtesy of a private tasting room, patio and a high-end steakhouse, Cypress & Oak, whose décor of dark wood contrasting with rich jewel tones, was a throwback to classic steakhouses of the 1940s and 1950s.

The impressive bar specializes in craft cocktails, and the open kitchen offers expertly roasted dishes prepared over an open fire using a selection of Kentucky-raised beef and private reserve steaks.

If you want to stay local for dessert, opt for the Kentucky Brown Butter Cake, a moist concoction that is lip-smackingly delicious.

A nightcap in the elegant bar is the perfect send-off to dreamland.

The Ashbrook

Frankfort, Franklin County

No repurposing of a historic property in the Bluegrass Region has been as eagerly anticipated as that of the elegant mansion in Frankfort's historic district often referred to as "the Queen on the Corner."

The 14-room Ashbrook is the very picture of Southern gentility – no surprise as in the 19th century it was the home of E.H. Taylor, founder of Buffalo Trace Distillery, and a lion in Kentucky's bourbon industry.

Guests enjoy their pre- or post-dinner bourbon the way Taylor did – in front of the fireplace in the Ashbrook's first floor library lounge.

Speaking of dinner, be sure to book a table in the Field Note, the hotel's restaurant where Southern cooking has been elevated to new heights, and there's a bourbon from the well-stocked bar that perfectly pairs with every dish – whether it's pork belly with goat cheese, fig and balsamic with fresh herbs for an appetizer; salmon with miso butter, pomegranate and asparagus for a main, or chocolate tart with ganache, meringue and blueberry for dessert.

The historical roots of the Ashbrook inspired Common Bond to retain original features such as the Rookwood tile in the bathrooms and to add custom-designed reproduction furniture in the guestrooms.

With both the Ashbrook and its sister property, the Delegate, Kentucky's capital city now has two capital hotels.

Hotel Thoroughbred

Paris, Bourbon County

Bourbon County has long had a tradition of breeding racing champions, and in the spirit of that tradition, there's a new Thoroughbred in the county. But this one doesn't have four legs - instead it has 19 meticulously curated rooms which reflect the town of Paris's motto, "Horses, History and Hospitality."

All three have been an integral part of Paris's identity since its founding in 1776. However, the hospitality part didn't get a boost from a boutique hotel until Hotel Thoroughbred officially opened its doors in April of this year.

As a hotel, it may be less than a year old, but as a structure which has retained the architectural integrity of the town's Main Street, it dates to 1891 when a local merchant built a three-story Romanesque/Victorian building to house his furniture and cabinetry business. The building is now listed on the National Register of Historic Places.

Located just across from Secretariat Park, Hotel Thoroughbred is a fitting homage to the Bluegrass Region's signature industry.

The façade has a stunning mural of Sunday Silence winning the 1989 Kentucky Derby. The lobby features a wall with paddock fencing from Claiborne Farm and jockey silks suspended from the ceiling. Rooms and suites have equestrian themes and names such as the Stallion, the Filly, the Foal and in an amusing twist, the Bridle Suite.

There is no onsite restaurant, but it does have a bar, the Starting Gate, where guests can enjoy a glass of bourbon (you are in Bourbon County after all).

If you need any further convincing, Garden & Gun Magazine has already given its stamp of approval, referring to Hotel Thoroughbred as "a Hot Southern Hotel to Watch."

The Woodford Hotel

Versailles, Woodford County

One could say that the Woodford Hotel in downtown Versailles is experiencing its second act or would that be third or fourth act? Regardless, the latest incarnation is doing it in style.

The building's history as a stop for weary travelers began in 1800 when a relative of Henry Clay opened the Watkins Inn, making it the first tavern in Versailles.

By the mid-1800s, it had changed its name to the Old Versailles House, but not its purpose – as the newly renamed establishment advertised that it "would entertain travelers on reasonable terms."

From 1881 to 1913, the building on Main Street served as the 28-room Hotel Woodford before closing its doors to overnight guests.

More than a century later, it has re-opened as a design-forward boutique (many of the character-defining features such as the cornice and long, narrow windows are intact today) with eight bourbon-themed suites, each named for a Kentucky bourbon.

That means you're in luck if your favorite bourbon happens to be Buffalo Trace, E.H. Taylor, Pappy Van Winkle, Four Roses, Wild Turkey, Blanton's, Old Crow or Woodford Reserve.

There is also a beautifully decorated downstairs common room, making the Woodford Hotel a perfect choice for a family vacation, girlfriends' getaway or wedding party.

The Aldenberg Hotel

Versailles, Woodford County

With the opening of the 29-room Aldenberg in 2025 in the former Woodford Bank & Trust Building, Woodford County got a second property that plays on the county's bourbon heritage.

However, this one took it a step further and added an equine component to its design element.

What could be more Bluegrass Region than bourbon and horses?

While guests won't find any Thoroughbreds hitched to the rail in the parking lot, they will get up close and personal with the bourbon.

Beginning next year, guests can get a tour of Kentucky's first craft distillery within a hotel. They will be able to watch the distilling process in the custom copper still located near the side entrance to the property.

The hotel's specialty bourbon (currently being produced offsite) is called Keyholder's Reserve 10 Year Old, available exclusively at The Aldenberg and its onsite restaurant, Silk's Steakhouse.

If you are more of a wine lover, Silk's offers a topnotch wine list with names like Moet & Chandon, Veuve Clicquot, Cloudy Bay and Chateau Mont-Redon to accompany the cuisine of chef Jon Baugh, who trained in Michelin-starred restaurants before returning to his native Kentucky.

When it comes to design, The Aldenberg has retained touches from its 19th century past (heirloom wood, polished brass, original architectural details) while celebrating the present (a rooftop bar to catch the last rays of a golden Bluegrass sunset).

The Dowling House

Lawrenceburg, Anderson County

Typically, Air B&Bs have appealed to those who want a home away from home when they are traveling. While serviceable, Air BnBs rarely display the charm of a bygone era and historical importance.

This is definitely not the case for the three-story white mansion in Lawrenceburg's downtown. Built in 1886, it was home to Mary Dowling, and if that name doesn't ring a bell, it should – particularly if you consider yourself a bourbon aficionado. In these parts, Mary Dowling is known as "the Mother of Bourbon."

At a time when most women were baking pies and birthing babies, Mary Dowling was bootlegging bourbon. After her husband's death, she inherited his share in a distillery, making her one of the few women in the industry.

In addition to business savvy (during Prohibition she sold part of her inventory to distilleries allowed to make bourbon for medicinal purposes), Mary had moxie to spare.

In defiance of the federal government, she continued making bourbon and transporting it to Mexico. Thumbing her nose at authority earned her both the funds for maintaining her beloved mansion and three years tied up in court.

After prevailing over the legal system, she moved to Juarez, Mexico where she continued to run her distilling operation.

No doubt she left part of her heart in her Lawrenceburg mansion, so don't be surprised to see her ghost roaming the corridors.

The lower floor of the Dowling House functions as an event space, but for clued-in visitors, the second and third floors are available as a three-apartment Air BnB that will sleep 18, making it ideal for family or friends.

Note: The entire house must be rented out to any overnight guests.

While furniture is a mix of modern and antique reproductions, there are many original features remaining, including floors on all three levels, unpainted wainscoting and trim, stairs and railings, and the spectacular stained-glass window over the second-floor staircase.

These will surely delight guests – that is if they don't mind sharing it with the specter of the Mother of Bourbon.

On your next visit to the Bluegrass Region, plan to sleep in the lap of luxury (and the arms of history) at one of the region's boutique hotels.