Aisling House - Historic Hospitality

Top rated by guests
Aisling House - Historic Hospitality House in Kentucky
Aisling House - Historic Hospitality House in Kentucky
Aisling House - Historic Hospitality House in Kentucky
Aisling House - Historic Hospitality House in Kentucky
Aisling House - Historic Hospitality House in Kentucky
Don't miss out! Price and availability may change
10 / 10
Outstanding(2 Ratings)

House in Kentucky

16 guests · 7 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Rooms

Bedroom 1
1 King
Bedroom 2
1 King
Bedroom 3
1 King
Bedroom 4
1 Queen
Bedroom 5
2 Queens
Bedroom 6
1 King
Bedroom 7
1 King

About this house rental

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. -- 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 & outdoor activities - Electric fireplaces - 3 washer & dryer sets 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 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 (golf chipping & driving, cornhole, croquet) CHEF'S KITCHEN - 2 sinks, 2 dishwashers, 2 refrigerators, 2 ovens, 60" gas range - Attached scullery (butler's pantry) - 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 front entrance - Step-free entry from driveway, through the garden, to the kitchen - 1st-floor library suite (upon request) - 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 indoor smoking; tobacco use outdoors only - No pets allowed - No events, parties, or large gatherings without prior written approval from the Guest Contact. The total number of guests must not exceed the maximum occupancy at any time. Please reach out to the Guest Contact after booking to coordinate events - 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

Amenities at Aisling House - Historic Hospitality

Free WiFi/internet
Free Parking
Air conditioning
Non-smoking
TV
Heating
Coffee/tea maker
Kitchen
Kitchenette
Balcony/Terrace
Dishwasher
Dryer
Patio
Kitchenware
Garden
Sauna
Fireplace
Private entrance
Shower
Bathtub
Outdoor Cooking
Family friendly
Ironing facilities
Outdoor dining area
Free toiletries
Towels
Linens
Dining table
Desk
Accessible by stairs only
Hairdryer
Closet
Contactless check-in/out
Carbon monoxide detector

Map of Kentucky


Ratings and reviews

10 / 10
Outstanding(2 Ratings)
10 / 10Outstanding·Aug 2026
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.
10 / 10Outstanding·Aug 2026
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!

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Aisling House - Historic Hospitality. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Aisling House - Historic Hospitality pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Aisling House - Historic Hospitality?

We found 34 amenities for this rental. This includes free wifi/internet, free parking, air conditioning, non-smoking, and tv.