Charming Victorian Apartment | Downtown Winchester

Summary:

Step into this charming Victorian apartment in the heart of downtown Winchester, KY. The 2-bedroom, 1-bath layout features a cozy living room with a decorative fireplace and smart TV, a fully equipped kitchen, and in-unit laundry. Both bedrooms offer blackout curtains and reading chairs; the shared bath includes a shower and soaking tub. Pets welcome! Free parking behind the building and on the street. The perfect base for exploring Winchester's local scene and the Kentucky countryside.



The Space:

NOTE: After booking confirmation, you will receive a short pre-arrival form from property management to be completed prior to arrival.



ACCESS TYPE:

▻ Guests will have access to the entire 1st floor apartment.



PROPERTY LAYOUT:

FIRST FLOOR

▻ Living Room: Smart TV, decorative fireplace, stackable washer/dryer, Keurig coffee maker

▻ Kitchen: Electric stove, oven, microwave, full-size refrigerator, dishwasher

▻ Bedroom 1: 1 Queen bed, closet, reading chair, blackout curtains, ceiling fan

▻ Bedroom 2: 1 King bed, Smart TV, walk-in closet, reading chair, blackout curtains

▻ Bathroom: Full bath — shower + soaking tub + toilet + sink, linen closet



HIGHLIGHTS

▻ Charming ground-floor apartment in a beautifully preserved 1900 Victorian building

▻ Cozy living room with decorative fireplace and smart TV

▻ Fully equipped kitchen with electric stove, dishwasher, and full-size refrigerator

▻ In-unit stackable washer and dryer — no laundromat runs needed

▻ Both bedrooms feature blackout curtains and reading chairs for restful nights

▻ Full bath with both a shower and a soaking tub

▻ Self check-in via smart locks on front and back doors

▻ Ample free parking — 5+ spots behind the building plus street parking

▻ Pet-friendly — dogs welcome!

▻ Downtown Winchester location, steps from local dining and shops



ACCESSIBILITY

▻ Ground-floor, single-level apartment with no interior stairs. Steps going up the entry door.



Guest Access:

PARKING

▻ 5+ dedicated outdoor parking spots available behind the house off the alley at no charge. Free street parking available along S Maple St.



ENTERING THE HOME

▻ The Home is Accessed Via Self Check-In Using a Smart Lock with a Unique Code Per Guest.



The Neighborhood:

🌳 Surrounding Area

▻ Downtown Winchester Core — 2 min walk (Main St shops, local restaurants, local character)

▻ Ale-8-One Bottling Company — 5 min drive (birthplace of Kentucky's iconic local soda)

▻ Fort Boonesborough State Park — 20 min drive (historic fort, Kentucky River access, camping)



🍽️ Dining & Cafes

▻ Main Street Winchester restaurants — 2–5 min walk

▻ Local cafes and eateries in downtown Winchester — walkable



🏘️ Nearby Towns & Cities

▻ Lexington, KY (Horse Capital of the World) — 20 min drive (dining, bourbon, horse farms)

▻ Richmond, KY — 20 min drive (Eastern Kentucky University, shops)

▻ Paris, KY — 20 min drive



🍷 Bourbon & Spirits

▻ Woodford Reserve Distillery — 35 min drive

▻ Kentucky Bourbon Trail distilleries (via Lexington) — 20–60 min drive



🏞️ Outdoors & Day Trips

▻ Red River Gorge Geological Area — 45 min drive (world-class hiking, rock climbing, natural arches)

▻ Natural Bridge State Resort Park — 55 min drive

▻ Daniel Boone National Forest — 45 min drive

▻ Kentucky Horse Park (Lexington) — 25 min drive



Getting Around:

GETTING AROUND:

▻ We recommend Uber or Lyft. We have not had any issues with either.





EVENT OR TOUR OPTIONS:

▻ If you are looking for a tour guide or event transportation in the area, please let us know! We would be happy to help.



Other Things to Note:

We take pride in offering a clean, comfortable, and welcoming space for your stay. The home is professionally cleaned and well-maintained, though minor signs of age may be present as this is a well-loved home rather than a hotel-style property. If anything needs attention, we’ll address it promptly to ensure a stress-free visit. We kindly ask that you treat the home as your own, and guests are responsible for any damages or loss, which should be reported immediately.



HOUSE RULES:

▻ Please do not unplug any electronics that are currently connected. Unplugging devices may result in a $100 fee.

▻ STRICTLY NO PARTIES, NO GATHERINGS, NO UNAUTHORIZED GUESTS, and a security deposit of $500 to $1,000 USD applies for local guest bookings.

▻ Please observe quiet hours between 10 PM and 8 AM

▻ Strictly No Smoking. Smoking of any kind, including cigarettes, cigars, e-cigarettes, vaping devices, or illegal substances, is prohibited anywhere in the property. Any violation may result in the immediate termination of your reservation without a refund, plus a $500 smoking violation fee to cover additional cleaning and remediation costs.

▻ Kindly keep noise and all activities neighbor-friendly, and avoid any community disturbance. Excessive noise, disruptive behavior, or any activity that disturbs the surrounding community may result in the immediate termination of your reservation without a refund plus a violation fee of $500.

▻ Please ensure pets are cleaned up after.

▻ Visitors and unauthorized guests are generally NOT allowed.



By booking this property, you agree to follow all rules and guidelines outlined in the listing. Failure to comply may result in a $500 fee, charged to the credit card used for the reservation.



POLICIES:

▻ Early Check-In – We’ll do our best to accommodate! Same-day requests depend on our cleaning team, and for future stays, the only guaranteed option is booking the prior night (if available).

▻ Luggage Drop – Luggage drop may be accommodated before check-in, but it is not guaranteed and must be approved by the host in advance. Approval depends on availability, cleaning schedule, and whether the property is ready for access.

▻ Late Check-Out – Late check-out is not guaranteed and requires host approval. Standard checkout applies unless approved. To guarantee a later stay, book the next night if available. Unauthorized late check-outs incurs violation fees.

▻ Package Delivery – We cannot guarantee safe or timely receipt of packages sent to the home. For reliability, we recommend using a local pick-up location or requesting doorstep delivery if sending items here.

▻ Pet Policy – We’re happy to welcome pets! A $150 non-refundable fee applies, plus $50 for each additional pet. This helps cover the extra deep cleaning to keep the home fresh for all guests.

▻ Third-Party Bookings are NOT permitted. The person making the reservation must be the primary guest staying at the property. Reservations made on behalf of someone else may be canceled or terminated without a refund if they do not comply with this policy.

▻ Mail Back Service - If you forget something, we can mail it back for a $50 fee (as long as it’s not an oversized item)

▻ Cancellation - Cancellation refunds will be based on your booking's cancellation policy

▻ There are exterior cameras installed above the front door and above the back door. It is on and recording 24/7 to help ensure the safety of you and the property during your stay.