Photo by Jeff Rogers /Lexington Convention and Visitors Bureau

B&B in Lexington

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B&B in Lexington

1. Chez Lyndon Manor

Chez Lyndon Manor
Northside District
$186
$223 total
includes taxes & fees
Sep 28 - Sep 29
Chez Lyndon Manor

2. Montgomery Inn BnB

Montgomery Inn BnB
Versailles
$183
$201 total
includes taxes & fees
Oct 5 - Oct 6
Montgomery Inn BnB

3. The Denny House

The Denny House
Paint Lick
$162
$173 total
includes taxes & fees
Sep 28 - Sep 29
The Denny House

4. The B & B at Queenslake

The B & B at Queenslake
Georgetown
$299
$329 total
includes taxes & fees
Sep 26 - Sep 27
The B & B at Queenslake

5. Charred Oaks Inn

Charred Oaks Inn
Versailles
$469
$517 total
includes taxes & fees
Oct 21 - Oct 22
Charred Oaks Inn

6. The Guest House

The Guest House
Lancaster
$124
$133 total
includes taxes & fees
Sep 26 - Sep 27
The Guest House
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Top neighborhoods in Lexington

Downtown Lexington

Downtown Lexington captivates with its well-preserved historical architecture and vibrant culture. Stroll cobblestone streets lined with antebellum mansions like the Mary Todd Lincoln House and Hunt-Morgan House. Catch a performance at the restored Lexington Opera House or enjoy Thursday Night Live concerts at Cheapside Park. Horse-drawn carriages clip past craft breweries while art galleries showcase local talent. Bourbon-focused gastropubs and farm-to-table restaurants offer authentic Kentucky flavors throughout the walkable district. Business hotels and boutique properties in converted historic buildings provide comfortable lodging options. The compact downtown core makes exploration easy with everything within a short walking distance.

Distillery District

Lexington's Distillery District breathes new life into historic bourbon warehouses. Converted industrial spaces now house artisan galleries, craft cocktail lounges, and farm-to-table restaurants where you can sample small-batch spirits. Live jazz and blues performances create a soundtrack for your exploration of this bourbon-focused cultural hub. The district is highly walkable with red brick buildings and warm amber lighting setting an intimate vibe. Boutique hotels in converted industrial buildings offer upscale lodging options. Though public transit is limited, downtown trolleys connect to main Lexington routes and ride-sharing is readily available.

Chevy Chase

Chevy Chase offers tree-lined streets with stately Colonial and Tudor mansions for travelers who appreciate architectural beauty. This upscale residential neighborhood provides a peaceful glimpse into affluent Lexington living, away from tourist crowds. Wide sidewalks and mature oak canopies create the perfect setting for leisurely walks through this historic area. You'll need to venture beyond the neighborhood for dining and shopping, as Chevy Chase maintains its purely residential character. Accommodation options include upscale bed & breakfasts in converted historic homes. Most visitors rely on cars or ride-sharing services to reach downtown attractions, just 10-15 minutes away.

Beaumont Residential

Beaumont's tree-lined streets offer a peaceful retreat from downtown Lexington's bustle. Families stroll along well-maintained sidewalks and kids play in tidy neighborhood parks. When you're ready to explore, Keeneland Racing Course and The Red Mile Racetrack are just a short drive away. Budget-friendly vacation rentals and extended-stay hotels make this quiet suburb an excellent home base. While dining options are limited to casual chain restaurants, downtown's diverse food scene is just 15 minutes by car. You'll need wheels to get around, but ample parking and uncrowded streets make driving stress-free.

North Upper Street

North Upper Street brings Lexington's heritage to life through bourbon culture and historic charm. The neighborhood's 19th-century brick buildings house distillery tasting rooms, art galleries, and the iconic Kentucky Theatre with its restored 1922 facade. Victorian storefronts blend with modern restaurant patios where live bluegrass music creates the perfect soundtrack for your evening stroll along lamp-lit sidewalks. Getting around this compact, walkable area is easy with bus routes and ride-sharing options readily available. After dark, the area transforms with craft cocktail bars and farm-to-table restaurants serving Kentucky specialties like hot brown. Boutique hotels in historic buildings offer bourbon-themed amenities that complete your authentic Lexington experience.

Top landmarks in Lexington

A large white house with multiple towers on a grassy hill under a cloudy sky.

Keeneland Racing Course

9.2/10 (1,084 reviews)
Wanna race? You could pay a visit to Keeneland Racing Course located 5.9 mi (9.5 km) from central Lexington.
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A nighttime cityscape with illuminated buildings and streets.

Rupp Arena

8.8/10 (1,287 reviews)
You could catch an event at Rupp Arena, a stadium in Downtown Lexington. If you think Rupp Arena is cool, you also might like Lexington Memorial Coliseum and Legends Field, both located nearby.
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A modern building with glass facades and a landscaped courtyard.

Lexington Convention Center

8.2/10 (405 reviews)
Lexington Convention Center is worth a pic or two when discovering Downtown Lexington.
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A brightly lit Christmas tree in front of a building with colorful lights.
Photo by Hyelsinta

Fayette Mall

8.8/10 (1,184 reviews)
If you like shopping, take time out to go to Fayette Mall when in Lexington. Splash some more cash at The Mall At Lexington Green.
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A brick building with arched entrances and posters for 'The Great Gatsby' and 'Sister Act'.
Photo by Hyelsinta

Lexington Opera House

8.0/10 (165 reviews)
If you want to see a show while you're in town, try and grab some tickets at Lexington Opera House in Downtown Lexington. If you enjoy the show and want to see another, Downtown Arts Center, Lexington Ballet Company, and Red Barn Radio are all a short walk away.
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Red Mile Racetrack

8.0/10 (130 reviews)
Red Mile Racetrack is 1.2 mi (2 km) from central Lexington, why not stop by during your stay.
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Kroger Field

8.6/10 (660 reviews)
You can catch an event at Kroger Field, located 1.8 mi (2.8 km) from central Lexington. If you think Kroger Field is cool, you also might like Lexington Memorial Coliseum and Rupp Arena, both located nearby.
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Hamburg Place

8.8/10 (434 reviews)
If you want to give your credit card some exercise, head out to Hamburg Place in Liberty Area. Splash some more cash at Hamburg Pavilion.
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Lexington and related destinations

Bourbon distilleries and horse farms surround this spirited college town where the University of Kentucky Wildcats inspire near-religious devotion. At Kentucky Horse Park, magnificent thoroughbreds showcase the region's equine obsession. The historic Mary Todd Lincoln House offers glimpses into the First Lady's early life. Downtown's Arts District buzzes with galleries and the ornate Lexington Opera House hosts performances in Victorian splendor. Keeneland Race Course combines architectural elegance with heart-pounding races each spring and fall. Between bourbon tastings, explore the Singletary Center's cultural offerings or catch ice skating at Lexington Ice Center. The Hummel Planetarium provides stellar entertainment when you've had your fill of earthly pleasures.

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A white wooden fence leading to a large building with two towers.
Photo by Lexington Convention and Visitors Bureau/Gene Burch

Find out more about Lexington

Lexington is also notable for its theater. Activities like horseback riding give you a chance to enjoy the outdoors while you're in town. Learn about the local heritage of Lexington at landmarks like Lexington Opera House and Mary Todd Lincoln House. Check out other sights like Lexington Convention Center and Rupp Arena.

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