Stay at Aisling House
A restored Victorian home in Winchester, Kentucky offering boutique lodging and a distinctive stay in the heart of the Bluegrass region.
Historic Hospitality in Winchester
Aisling House offers a unique stay within a restored Victorian home built circa 1888, located in Winchester, Kentucky’s historic Thomson Subdivision. Designed for both comfort and character, the home invites guests to experience a slower pace—where shared spaces, architectural detail, and thoughtful restoration shape the experience.
Ideal for group stays, mini getaways, and those seeking a more memorable alternative to traditional lodging, Aisling House provides both proximity to downtown Winchester and the privacy of a full-home rental.
❋ Whole-Home AccommodationsSeven bedrooms, eight beds, and four full baths comfortably host up to 16 guests, offering both shared gathering spaces and private retreats.
❋ Historic Character, Thoughtfully RestoredOriginal architectural details remain at the heart of the home, carefully preserved and complemented by modern updates for comfort and ease.
❋ Walkable, Yet Set ApartLocated just minutes from downtown Winchester, Aisling House offers convenient access while maintaining a sense of quiet and separation.
❋ Designed for GatheringFrom the front porch to interior common spaces, the home is arranged to encourage connection, conversation, and shared time.
Inside Aisling House
From light-filled bedrooms to layered common spaces, the interiors of Aisling House reflect a balance of preservation and comfort.
Planning a Gathering?
Aisling House also serves as an intimate event venue, hosting weddings, celebrations, and private gatherings up to 50 guests.
The bedrooms at Aisling House are designed as a collection of private retreats, each offering its own character and sense of place within the home.
Thoughtfully appointed with king and queen accommodations, fireplaces, and refined details throughout, each room balances historic charm with modern comfort.
From the Primary Suite to the Attic Suite above, the spaces are designed to accommodate both gathering and retreat — offering comfort, privacy, and flexibility for every stay.
Bedrooms & Suites
Library Suite
A flexible main-floor retreat with private access and quiet separation
King Murphy Bed
Handicap Accessible Bathroom
Amenities: fireplace, television, dedicated workspace, wardrobe, front porch access
The Library in its bedroom configuration offers a Suite with a quiet, private retreat on the main floor of the house. Designed for both comfort and accessibility, it is ideal for a host, honored guest, or those who prefer to avoid stairs. With close proximity to the main living spaces, a full bath nearby, it provides both connection and separation in equal measure.
This suite features a king bed, fireplace, television, dedicated workspace, wardrobe available in parlor, and private access to front porch and library terrace.
Family Suite (Second Floor)
A connected suite designed for shared stays with privacy
Designed for families or guests traveling together, the Second Floor Family Suite offers two private bedrooms connected by a shared Jack and Jill bath, with access to the main hall.
The Green Room is light-filled and airy, with a quiet sitting area and private porch access.
The Gold Room is warm and refined, layered in rich tones for a more intimate retreat.
Each room features a king bed, fireplace, television, dedicated workspace, and closet — offering both comfort and privacy within a shared suite.
Primary Suite (Second Floor)
A refined private retreat with layered architectural detail
King Bed
Amenities: clawfoot tub, walk-in shower, fireplace, television, closet storage
This Suite is the most refined private space in the home, offering a quiet retreat on the second floor.
Coffered ceilings, soft natural light, and layered architectural details create a sense of calm and understated luxury.
The marble bath features a restored clawfoot tub and walk-in shower, blending historic character with modern comfort.
Complete with a king bed, fireplace, television, and ample closet storage, the suite is designed for extended stays, bridal preparation, or a private escape within the house.
The Blue Room
A calm, light-filled bedroom with direct connection to the attic suite
Queen Bed
Amenities: fireplace, closet, dedicated workspace, in-room laundry, Attic Suite access
The Blue Room offers a calm and understated retreat on the second floor.
Soft tones and natural light create a relaxed atmosphere, while classic details reflect the character of the home.
Furnished with a queen bed, fireplace, closet, and dedicated workspace, it provides a comfortable and practical space for guests.
A discreet in-room laundry is thoughtfully integrated within one of the closets, offering added convenience for extended stays. The Blue Room also provides direct access to the Attic Suite, making it well-suited for families or groups seeking a more connected layout within the home.
Attic Suite
A quiet upper-level retreat designed for separation and extended stays
The Attic Suite offers a private retreat above the main levels of the home, creating a quiet and more secluded experience.
The suite includes two distinct bedrooms: the Attic Study, with two queen beds and a large dedicated workspace for 4, and the Attic Primary, featuring a king bed. Each room includes a closet and is thoughtfully designed for comfort and extended stays.
The shared bath features a fireplace and restored original clawfoot tub overlooking the garden —bringing together historic detail and quiet refinement.
Accessed through the Blue Room, the suite serves as a natural extension of the home, ideal for families or groups seeking both connection and privacy.
Shared Spaces
The Parlor
A flexible main-floor retreat with private access and quiet separation
The Parlor, historically the home’s formal receiving room, is situated just beyond the foyer.
Defined by original architectural detailing and morning light, the space is centered around a restored tiger oak fireplace, an enduring feature of the home’s nineteenth-century craftsmanship.
Traditionally used for receiving guests, the room continues to serve as a setting for conversation and quiet repose, offering a composed and gracious introduction to the home.
The Library
A connected suite designed for shared stays with privacy
The Library serves as a traditional reading room and private retreat within the home, situated on the main floor.
Defined by original architectural detailing, the space is anchored by a coffered ceiling and original craftsman bookcases, with natural light softening the dark room. A fireplace and television allow the space to function comfortably for multimedia morning or evening use.
Well-suited for reading, study, or quiet conversation, the Library offers a more intimate setting within the house, with direct access to both the front porch and the Library Terrace.
Historically a place of reflection and respite, the room remains a setting for quiet retreat, balancing connection to the home with a sense of separation.
The Dining Room
A refined private retreat with layered architectural detail
The Dining Room serves as a more intimate setting for shared meals and conversation, situated on the main floor.
Defined by original architectural detailing and natural light, the space is anchored by an 1800s grand marble mantel and a large Empire chandelier, establishing a sense of proportion and historic character.
Arranged to seat eight, the room offers a composed setting for dining, with additional seating at either end of the room for daily use and conversation. It remains a welcoming space for meals and connection, complementing the home’s larger entertaining areas.
The Kitchen
A calm, light-filled kitchen with direct connection to the butler’s pantry, ballroom, dining room, and kitchen terrace.
The Kitchen serves as a central gathering space within the home, situated on the main floor and connected to both interior and outdoor living areas.
Defined by bold cabinetry and original architectural context, the space balances modern function with the character of the home. A 60-inch gas range, large refrigerator, and commercial ventilation support full-scale preparation, while a twelve-foot island with seating provides ample space for gathering and service.
A dedicated workspace with a chaise lounge offers a more relaxed setting within the room, allowing the Kitchen to function beyond preparation alone.
With direct access to the Dining Room, Ballroom, and the outdoor kitchen terrace, the space supports the natural flow of the house and is well-suited for both quiet mornings and larger gatherings.
The Ballroom
A refined multi-use space that accommadates a private dinner party or event.
The Ballroom serves as the home’s primary space for gathering and entertaining, situated along the rear of the main floor.
Defined by a black and white checkered floor and brass chandeliers, the room is shaped by both scale and light, creating a distinctive and expansive setting within the house.
Reimagined from a later addition and refined to reflect the home’s character, the space accommodates larger gatherings, events, and shared experiences.
Opening onto the Ballroom Terrace, and with direct access to the Kitchen, the space supports a seamless transition between interior and exterior settings and is well appointed for both formal occasions and extended gatherings.
The Promenade & Terraces
The Promenade extends along the rear of the home, connecting the Library, Ballroom, and Kitchen Terraces into a continuous sequence of outdoor spaces.
Conceived as an extension of the house, it allows for a natural progression between interior and exterior settings, supporting both movement and gathering.
Each terrace maintains a distinct character—the Library Terrace offering a more quiet setting, the Ballroom Terrace accommodating larger gatherings, and the Kitchen Terrace designed for preparation and informal dining.
Together, the Promenade and Terraces form a cohesive outdoor environment, for both daily use and larger occasions.
The Library Terrace
A flexible main-floor retreat with private access and quiet separation
The Library Terrace extends from the Library, offering a quieter outdoor setting along the Promenade.
Perfect for reading, morning coffee, or small conversation, the space reflects the more private character of the adjoining room, providing a calm and measured transition between interior and exterior.
The Ballroom Terrace
A connected suite designed for shared stays with privacy
The Ballroom Terrace extends directly from the Ballroom through three French doors, opening onto the gardens beyond.
Defined by its scale and connection to the home’s primary entertaining space, it supports a natural flow between interior and exterior settings.
For larger gatherings and outdoor use, the terrace provides a seamless transition from the Ballroom to the gardens, accommodating both formal occasions and extended gatherings.
The Kitchen Terrace
A refined private retreat with layered architectural detail
The Kitchen Terrace extends directly from the Kitchen, connecting to the outdoor kitchen and serving as a functional and social gathering space along the Promenade.
Defined by a twenty-foot island with seating, the terrace is designed to support preparation, serving, and informal dining. A 60-inch natural gas grill, outdoor sink, and integrated work areas allow for full outdoor use.
An outdoor television and fireplace with surrounding seating create a comfortable setting for extended gatherings, allowing the space to transition easily from daytime use to evening.