Entire home

Aisling House - Historic Hospitality

Photo gallery for Aisling House - Historic Hospitality

A study with a desk, chairs, bookshelves, and a radiator. - Aisling House - Historic Hospitality (Winchester)
A bedroom with a large bed, a bench with towels, a fireplace, and a chandelier. - Aisling House - Historic Hospitality (Winchester)
A porch with a white railing, a mailbox, and hanging flower baskets. - Aisling House - Historic Hospitality (Winchester)
A grand staircase leading to a door with a floral arrangement on a console table. - Aisling House - Historic Hospitality (Winchester)
A kitchen with grey cabinets, a wooden countertop, and a window with a view. - Aisling House - Historic Hospitality (Winchester)
Aisling House - Historic Hospitality provides amenities, such as a garden and a sauna.

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms4 bathrooms446 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

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About this property

Aisling House - Historic Hospitality

  • Award-Winning 1891 Queen Anne Victorian

    Documented in the 1979 Survey of Historic Sites in Kentucky and recipient of the 2026 Clark County–Winchester Heritage Commission Historic Preservation Award.

    Experience 4,800 sqft of elegantly appointed interiors, including a ballroom with dining for 16, chef’s kitchen, and scullery. Enjoy 2,000 sqft of outdoor living across the promenade and historic front porch, complemented by a full outdoor kitchen, infrared sauna, greenhouse, and gardens

    -- THE PROPERTY --

    INDOOR LIVING
    - Original & restored architectural details throughout
    - 2 original clawfoot soaking tubs
    - Curated, elegant furnishings & décor
    - Formal parlor
    - Formal dining room (seats up to 8)
    - Ballroom (seats up to 16) w/ French doors to the terrace
    - Library w/ original built-in bookshelves & private book collection, w/ access to both a private terrace & the front porch
    - Board games and indoor entertainment (stored in the dining room’s Bombay dresser)
    - Electric fireplaces
    - 3 washer & dryer sets (2 on the 1st floor in the Scullery, 1 on the 2nd floor in the Blue Room)

    INTERNET, WORKSPACES & MEETINGS
    - 5G fiber internet throughout property
    - Dedicated workspace in every bedroom
    - Library workspace w/ wireless printer
    - Attic Study w/ 4 workstations & wireless printer; one workstation includes a monitor & laptop stand
    - Electrified greenhouse workspace (seats 4)

    SLEEPING ARRANGEMENTS
    - Bedroom 1 (Primary Suite): 1 king bed
    - Bedroom 2 (Green Room): 1 king bed
    - Bedroom 3 (Gold Room): 1 king bed
    - Bedroom 4 (Blue Room): 1 queen bed
    - Bedroom 5 (Attic Study; Access via Blue Room): 2 queen beds
    - Bedroom 6 (Attic Primary; Access via Blue Room): 1 king bed
    - Bedroom 7 (Library Suite; Converts to Bedroom Upon Request): 1 king Murphy bed
    - Bedrooms 5 & 6 (Attic Suite) are accessed through the Blue Room via stairs

    OUTDOOR LIVING
    - 1,700-sq-ft promenade w/ access to library, ballroom & kitchen terraces
    - Expansive front porch w/ 6 rocking chairs & multiple seating areas
    - Outdoor kitchen w/ gas grill, entertainment space & TV
    - 4-person sauna
    - Greenhouse w/ electricity for working, reading & relaxing
    - Landscaped gardens w/ donated historic plants
    - Outdoor games: corn hole, golf chipping, golf driving, and croquet (found in the greenhouse side entrance)

    CHEF'S KITCHEN
    - 2 sinks, 2 dishwashers, 2 refrigerators, 2 ovens, 60" gas range
    - Attached scullery
    - Drip & pod Keurig coffee maker, stove espresso, coffee bean grinder, milk steamer
    - Fully stocked w/ cookware, bakeware, utensils, glassware, dishware & flatware
    - Designed for kosher cooking

    ACCESSIBILITY
    - 3-story home, 10 steps to enter front door
    - Step-free entry via low-grade kitchen path from driveway
    - 1st-floor bedroom (Library) & accessible bathroom
    - Attic study & attic primary bedrooms accessed via blue room

    PARKING
    - 185-ft driveway accessible via either the front or back of property (8 vehicles)
    - Free street parking in front of home (first-come, first-served; up to 4 vehicles)
    - Trailer, horse trailer & RV parking OK

    -- THE LOCATION --

    - 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)

    -- REST EASY WITH US --

    Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

    -- POLICIES --

    - No smoking of any kind inside the home
    - Indoor vaping will trigger all hardwired, interconnected fire alarms
    - Outdoor smoking is restricted to tobacco only; cannabis and illicit drugs are strictly prohibited on the property
    - No pets allowed
    - No events, parties, or large gatherings without prior written approval from the guest contact
    - Quiet hours (9:00 PM–8:00 AM); outdoor music, games, shouting, and loud conversations are strictly prohibited during this timeframe
    - No shoes allowed upstairs
    - Please treat all furnishings with care
    - Additional fees and taxes may apply
    - Photo ID may be required upon check-in


    ADDITIONAL INFORMATION
    - Please reach out to the Guest Contact after booking if your group requires the library suite configuration

    SECURITY CAMERA INFORMATION
    - 4 exterior solar security cameras
    - Location: front entrance, driveway, kitchen terrace gate, garden gate
    - Coverage: exterior property access points

Property amenities

Pool/Spa

  • Sauna

Internet

  • Available in the house: Internet access

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 7 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Books
  • DVD player
  • Games
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 4,800 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Winchester is home to this holiday home. Bluegrass Heritage Museum and Kentucky River Museum are cultural highlights, and some of the area's activities can be experienced at Southwind Golf Course and Cassell Creek Golf Course. Visit our Winchester travel guide
View more Holiday homes in Lexington
Map
Winchester, KY

What's nearby

  • Clark County Public Library
    5 min walk - 0.4 km
  • College Park
    8 min walk - 0.7 km
  • Bluegrass Heritage Museum
    9 min walk - 0.8 km
  • Winchester Opera House
    11 min walk - 0.9 km
  • The Holler
    2 min drive - 2.4 km

Getting around

  • Lexington, KY (LEX-Blue Grass)
    37 min drive

Restaurants

  • Taco Bell
    2 min drive
  • 7 Brew Coffee
    4 min drive
  • Sonic Drive-In
    4 min drive
  • Dairy Queen
    17 min walk
  • Popeyes Louisiana Kitchen
    4 min drive

Frequently asked questions

Is Aisling House - Historic Hospitality pet-friendly?

No, pets are not allowed at this property.

How much is parking at Aisling House - Historic Hospitality?

On-site parking is available at the property.

What time is check-in at Aisling House - Historic Hospitality?

Check-in begins at 4:00 PM.

What time is check-out at Aisling House - Historic Hospitality?

Checkout is at 10:00 AM.

Where is Aisling House - Historic Hospitality located?

Situated in Winchester, this holiday home is within a 10-minute walk of Clark County Public Library, GRCHS Baseball Field and College Park. Bluegrass Heritage Museum and Winchester Opera House are also within 15 minutes.

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Reviews

Aisling House - Historic Hospitality Reviews

10

Exceptional

Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

Reviews

From a partner site

10/10 Excellent

FIVE STAR

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!
From a partner site

10/10 Excellent

Love for Aisling House

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.
From a partner site

10/10 Excellent

Comfortable and accessible

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.