Entire home

Aisling House - Historic Hospitality

Photo gallery for Aisling House - Historic Hospitality

Front Side View of Porch
Patio and Outdoor Dining Area Off Kitchen
Dining Room
Library
Kitchen

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Walk to Bluegrass Heritage Museum
7 bedrooms4 bathroomsSleeps 16

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill
  • Balcony

Explore the area

View in a map
Winchester, KY
  • Place, Bluegrass Heritage Museum
    ‪9 min walk‬
  • Place, Winchester Opera House
    ‪11 min walk‬
  • Place, Wiseman Park
    ‪2 min drive‬
  • Airport, Lexington, KY (LEX-Blue Grass)
    ‪33 min drive‬

Rooms & beds

7 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Queen Beds

Bedroom 6

1 King Bed

Bedroom 7 (Library)

1 King Bed

4 bathrooms

Full Bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Spaces

Deck or patio
Kitchen
Balcony
Garden

About this property

Aisling House - Historic Hospitality

1891 Restored Queen Anne Victorian | Outdoor Kitchen | Sauna

Nestled within Winchester’s Thomson District, a nationally recognized historic place, Aisling House offers 7 bedrooms, an iconic porch, 1,700 square feet of patio, a greenhouse, chef’s kitchen and scullery, outdoor kitchen, and elegant gathering rooms across nearly 4,800 square feet. Convenient to Blue Grass Airport, Lexington, Keeneland, Kentucky Horse Park, Red River Gorge, and the Bourbon Trail.

-- THE PROPERTY --

INDOOR LIVING
- Multiple dining areas, formal dining room and ballroom
- Electric fireplaces
- 4-person sauna
- Historic library w/ original bookshelves
- 3 washer & dryer sets
- Desk workspace, printer, monitor

SLEEPING ARRANGEMENTS
- Bedroom 1: 1 king bed
- Bedroom 2: 1 king bed
- Bedroom 3: 1 king bed
- Bedroom 4: 1 queen bed
- Bedroom 5: 2 queen beds
- Bedroom 6: 1 king bed
- Bedroom 7 (Library): 1 king bed

OUTDOOR LIVING
- Front porch
- Outdoor kitchen w/ gas grill
- Outdoor dining, TV

KITCHEN
- Chef's kitchen w/ attached scullery
- 2 sinks, 2 dishwashers, 2 fridges (small & full-sized), industrial oven
- Drip/pod Keurig, moka pot
- Cooking basics, dishware & flatware
- Designed for kosher cooking
- Walk-in pantry

ACCESSIBILITY
- 3-story home, 10 steps to enter front door
- Step-free entry available via kitchen path from driveway
- 1st-floor bedroom & full bathroom
- While there are 10 steps at the front door, a step-free path leads from the driveway to the kitchen entrance and the first-floor bedroom

PARKING
- Long driveway (8 vehicles)
- Trailer, horse trailer & RV parking

-- THE LOCATION --

- 0.5 miles to Main Street: restaurants, cafes, antiques
- Easy access to I-64 & I-75
- Over 10 horse stables & equestrian centers within 20 miles
- 29 miles to Keeneland
- 23 miles to Lexington, University of Kentucky, Rupp Arena, UK Football Shuttle
- 15-45 miles to Bourbon Trail distilleries
- 29 miles to Red River Gorge Geological & Site Natural Bridge State Resort Park
- 29 miles to Blue Grass Airport (LEX
- 99 miles to Cincinnati

-- 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
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in

SECURITY CAMERA INFORMATION
- 4 solar security cameras
- Location: front of the house, both driveways, gate to outdoor kitchen
- Coverage: whole property

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 20310467
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

About the area

Winchester

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. Take the opportunity to explore the area for outdoor excitement like hiking.
Map
Winchester, KY

What's nearby

  • Clark County Public Library - 5 min walk - 0.4 km
  • Bluegrass Heritage Museum - 9 min walk - 0.8 km
  • Winchester Opera House - 11 min walk - 0.9 km
  • Winchester Traveling Trail - 2 min drive - 2.1 km
  • Wiseman Park - 2 min drive - 2.8 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Taco Bell - ‬2 min drive
  • ‪Dairy Queen - ‬4 min drive
  • ‪Wendy's - ‬5 min drive
  • ‪7 Brew Coffee - ‬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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

Reviews

From a partner site

10/10 Excellent

Sharon

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

Cassie

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.
Response from VrboOwner on 15 Aug, 2026
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!

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