Holiday rentals in Carlisle

The Concord - Enjoy the Vineyard Views

Experience tiny home living without giving up the comforts of home. Kick back and relax in this modern 'spacious' tiny home loaded with the most up to date amenities - and Vineyard views right out your front door! This one bedroom home offers additional space for the family and kids with an upstairs loft and a roomy living area. Added bonus - you're a short walk to our family owned winery and restaurant! Plus- many historic attractions just a short drive away. Come enjoy the luxury tiny life.

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

The Bank House on Main St.

Come experience this unique Airbnb. In 1861, the Bank House was home to Bracken County’s first bank. This 1st-floor apartment still features the original tin ceiling and exposed brick from the 1800s. It will comfortably sleep 4-5 with a queen bed, a twin-over-full bunk (in a semi-private area), and two baths. Steps away from the Beehive, Augusta Pub, Carotas Pizzeria, Tabletop Traditions & the General Store. 2.2 mi - Soli Tree venue. 0.5 mi - Augusta Distillery. 1.2 mi - Baker Bird Winery

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our 3 newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

The Spring Valley Inn - charming rural home

Nestled only 4 miles outside of historic Paris, Kentucky this charming home will allow you and your guests to immerse yourself in the beautiful surroundings of Thoroughbred horse country. On your drive to the home pass horse farms such as Oak Lodge, Brandywine, and Adena Springs; all recognizable names from past Kentucky Derby runners. Enjoy your stay with room for your family not only indoors but out. Sit on the patio soaking in nature and local sounds from neighboring farm animals.

Modern Trailer Living

Freshly painted, updated and fully furnished, towels, tp/pt, most kitchen utensils, microwave, coffee pot/press, full size stove and fridge, TV in living room, wi-if when accessible must hv ur own streaming device, outdoor porch with smoking Ok!! This is a non smoking space!!!! No Smoking/vaping in unit, if you do a charge will be imposed!!!! No exceptions!! if you’re not a registered guest here you must park outside the gate which remains closed/opened but remains closed otherwise!

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 non-gentrified 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.

Haymark Farmhouse: cozy, country memories

Welcome to Haymark Farmhouse, built in 1907. Relax in front of the fireplace with electric logs, play games (provided), and cook in the well-supplied kitchen or on the gas grill out back. Enjoy the outdoor fire pit (wood provided) and the lighted sitting area and table for eight. Explore our 275 acre farm! Check out our cute farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ...Enjoy your time at Haymark Farm.

Quittin' Time - Country Cabin at Hickory Holler

Come visit the beautiful countryside and stay in this adorable cabin right outside the city limits of Cynthiana, KY! Located on over 90 acres, this place has a million dollar view of a large pond and huge pasture fields. It's only a short 5 mile drive into town where there is an abundance of local restaurants and small downtown shops. Enjoy a campfire with the on-site fire pit or go for walk and do some exploring. Come enjoy a very peaceful and quiet getaway!

Larkspur Cabin with Hot Tub near Red River Gorge

Located on the edge of Red River Gorge Geological Area in 20 acres of peaceful woodland and rolling hills, our property has the perfect blend of accessibility and seclusion. Enjoy birds at the porch feeders, and all the flowers blooming in the garden in the summer . Enjoy the hot tub! It's just 15 minutes from the Red River Gorge and Natural Bridge State Park and 5 minutes from Stanton for shops and restaurants.

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.