House
5

Aisling House - Historic Hospitality

Property ID: 553455WinchesterKYUS
Sleeps 167 BR4 BA
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Most trips qualify for free 48 hour cancellation. Add dates for more information.

Description

1891 Queen Anne Victorian

Thoughtfully restored historic home in Winchester’s nationally recognized Thomson District, with elegantly appointed rooms for resting and gathering across 4,800 square feet. Enjoy a chef’s kitchen and scullery, 1,700 square feet of terraces, a greenhouse, an outdoor kitchen, and seamless indoor-outdoor living. Convenient to Blue Grass Airport, Lexington, UK Football Shuttle, Rupp Arena, Keeneland, Kentucky Horse Park, Red River Gorge, and the Bourbon Trail.

Amenities

  • Free Parking
  • Essentials
  • Kitchen
  • Laptop Friendly
  • Central Heating
  • Central Air Conditioning
  • Wireless Internet (WIFI)
  • Washer

Map

Location Details

- 0.5 mi to Main Street: restaurants, cafes, antiques

- 2 mi to I-64; 17 mi to I-75

- 15-45 mi to Bourbon Trail distilleries

- 20 mi from 10 equestrian centers

- 23 mi to Lexington, University of Kentucky, Rupp Arena, UK Football Shuttle

- 27 mi to Kentucky Horse Park

- 29 mi to Keeneland

- 29 mi to Red River Gorge Geological Site & 38 mi to Natural Bridge State Resort Park

- 29 mi to Blue Grass Airport (LEX)

- 99 mi to Cincinnati; 95 mi to (CVG)

Reviews

5
4 reviews
  • Comfortable and accessible

    5/5

    My name is Betty. I am an 82-year-old woman with disabilities. There are places I cannot stay because they are not handicap accessible.

    Recently, I stayed at Aisling House, which was a wonderful change. I stayed in a space that was accessible, with everything I needed on the first floor. The bathroom was beside my space and had all the things I needed at hand.

    Unless a person is handicapped, they do not realize how important these things are.

    Betty
    Published September 3, 2026
    Manager's Response:

    Thank you, Betty! We are so glad our first-floor library suite and accessible bathroom made your stay at Aisling House comfortable. We truly appreciate you sharing your experience for future guests with similar needs. We would be honored to welcome you back again.

  • Time capsule

    5/5

    We stayed the weekend of the Kentucky Derby and were transported back in time. The moment you entered the front doors you are taken back to the 1800's. With rich appointments and cozy beds. It was perfection. We stayed in the library and watched the race on the huge TV hung over the cozy fireplace. Our stay was more relaxing than can be imagined. The rest of the house was huge plenty of space for a family reunion. The chefs kitchen was a dream. Thankyou for sharing you home with us.

    gwen
    Published August 26, 2026
    Manager's Response:

    Gwen, thank you so much for sharing this. We love that Aisling House became part of your Kentucky Derby weekend and that you were able to enjoy both the history of the home and the comforts within it. Knowing that you found the house relaxing and welcoming means a great deal to us. It was our pleasure to share Aisling House with you, and we would be honored to welcome you and your family back again.

  • Love for Aisling House

    5/5

    During my trip, I stayed in the dreamy attic room! The bathroom was an absolute sanctuary with a clawfoot tub with its fireplace view for a bath before curling up in the king-sized bed. A perfect experience after an evening spent on the terrace and out on the front porch for late-night rocking chair conversations. In the morning, the butler's pantry and kitchen are such a delight for their welcoming space and easy-going comforts. I loved this house. The library feels like a warm hug, and every room has something to offer here. I hope everyone picks out their favorite here.

    Cassie
    Published August 11, 2026
    Manager's Response:

    Cassie, thank you for such a beautiful review. We loved hearing how you experienced Aisling House and that you found favorite moments throughout the home. Creating a place where people can settle in, gather together, and truly enjoy the house is exactly what we hoped for. We are so glad the Attic Suite was yours for the stay, and we hope to welcome you back to find another favorite next time!

  • FIVE STAR

    5/5

    Unforgetable weekend in a beautifully restored Victorian home, perfectly appointed and decorated with period furnishings in every room except for 21st century beds, baths, and kitchen. Plenty of room for a small reunion or retreat. I will definitely reserve it again!

    Sharon
    Published August 10, 2026
    Manager's Response:

    Sharon, thank you so much for your kind review. We are delighted that you had such a memorable weekend at Aisling House. It means so much to us to hear that you enjoyed both the historic character of the home and the modern comforts throughout your stay. We would be honored to welcome you back again!

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5
4 reviews

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  • This property has a maximum occupancy of 16 guests, not including infants.
  • Pets are not allowed at this property.
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