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Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Dec 24 – 31

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Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Jul 23 – 30

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Haven on High Street Private Apt Historic Home

Haven on High St. Quiet-gracious-comfy-one bedroom apartment in 1842 home. Off street parking. King bed in bedroom, comfy queen sofa bed in living room, claw foot tub. Eclectic decor-a visual artistic treat. By design, the space is not kid or pet friendly. Fully furnished kitchen+coffee, tea, snacks. Private apartment-shared courtyard. Walk to coffee shop, UK, Rupp, downtown dining. Beautifully landscaped gardens with patio and porch seating. Host lives next door and available-as needed.

Aug 24 – 31

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Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

Jul 31 – Aug 7

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Close to Keeneland Charming Guest Suite

Great location in beautiful well established neighborhood. 5 mi to Keeneland & airport, 2 mi to downtown, Rupp Arena, Univ of Kentucky campus & football stadium. Centrally located within one mile of all major hospitals. Lexington is located along the Kentucky Bourbon Trail. Enjoy distillery, horse farm & historic home tours, unique and fine dining, craft breweries, sporting events, theater, concerts, boutique shopping. Nearby horse farms, rolling hills, hiking and boating/canoeing

May 14 – 21

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Charming & Cozy in Downtown Lexington

316 Hampton Court was designed for vacation rentals 110 years before the first air mattress was rented out on Airbnb. Built as apartments in 1920 on land owned by the Stoll family and named for their son in law, The Howard was bought and completely renovated in 2007. Now it has several vacation rentals behind its historic rounded door and up its oak staircase. This apartment is a cozy 650 square feet and was professionally reconfigured by one of Lexington's finest architects.

Dec 4 – 11

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Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Jul 5 – 12

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Lovely Downtown Apt 1 Block from Rupp!

Walk to Rupp and all downtown has to offer from this cozy, one bedroom apartment. The space is outfitted with a Smart TV, plush linens and towels, brand new washer/dryer, all new appliances, basic kitchen amenities and free off street parking on the premises for an effortless stay in downtown Lexington. If this is your first time booking with us, welcome! We look forward to hosting you again soon. if you have stayed with us before, thanks for your loyalty.

Feb 16 – 23

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Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Free parking for easy access to conventions, concerts, and games.

Jan 15 – 22

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Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

Feb 12 – 19

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Stay with our horses and goats on a private farm

Lovely and private studio barn apartment in super safe neighborhood. Stay with our horse and goats on 12 private acres, minutes from downtown Lexington. Hiking trails around property, and just minutes to several state parks. Three miles to 75 and 64, and 15 minutes to downtown Lexington, the Kentucky Horse Park, UK campus, and 10 minutes to the Hamburg area of Lexington full of restaurants, sports bars, and movie theaters. 50 amp EV charging station

Nov 4 – 11

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Nomi House, Renovated 1880's shotgun, downtown Lex

Registration ID '15082764-1' Enjoy your stay in comfort and style at the newly renovated NOMI House. Perfectly located in downtown Lexington, KY, walking distance to all the best restaurants and event spaces. Easy drive to equine experiences and the rolling hills of the Bluegrass state.

Aug 23 – 30

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River House - Cottage with KY River View & Access

Oct 9 – 16

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Moonlit Meadows: A Tranquil Getaway for Travelers

Aug 21 – 28

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City Chic Loft - Downtown

Aug 3 – 10

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Adorable, Clean Lexington Cottage, Convenient to Everything

Mar 3 – 10

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Bluegrass Country Cottage

Jul 6 – 13

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My Old Kentucky Home

Jul 16 – 23

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Updated historic home! Walk to Rupp/UK/restaurants

Sep 10 – 17

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Urban Chalet w/ Theater - Live. Work. Rejuvenate.

Oct 6 – 13

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