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Winners Circle - 2BR - Patio-Garage - Walk to Rupp

Photo gallery for Winners Circle - 2BR - Patio-Garage - Walk to Rupp

Interior
Interior
Living area
Interior
Room

Reviews

10 out of 10
Exceptional

Highlights

  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near University of Kentucky
2 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony
  • Free Wi-Fi

Explore the area

View in a map
Lexington, KY
  • Place, Rupp Arena
    ‪8 min walk‬
  • Place, Lexington Convention Center
    ‪14 min walk‬
  • Place, University of Kentucky
    ‪15 min walk‬
  • Airport, Lexington, KY (LEX-Blue Grass)
    ‪8 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Living Room 1

1 Queen Sofa Bed

2 bathrooms, 2 half bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 3

Soap · Toilet

Bathroom 4

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony

About this property

Winners Circle - 2BR - Patio-Garage - Walk to Rupp

Welcome to Winner's Circle! Stylish 3-story townhome in the heart of Lexington’s Distillery District, steps from Rupp Arena, Manchester Music Hall, Gatton Park, and the University of Kentucky. This upscale 2BR + pullout sofa home offers luxury design, fully stocked kitchen, smart TVs, blackout curtains, and private patio with bistro lighting, perfect for families, concertgoers, or exploring Bourbon Country.

Key Features

☀ Sleeps up to 6
☀ 2 full bathrooms + 2 half baths
☀ King + Queen + pull-out sofa
☀ Fully stocked kitchen, Nespresso & Keurig machines
☀ Private patio with seating & bistro lights
☀ Smart TVs, blackout curtains, walk-in closets
☀ Dedicated workspace with external monitor
☀ High speed internet
☀ Walkable to Rupp Arena, Manchester Music Hall, Distillery District

☆☆ BEDROOMS ☆☆

Primary (3rd floor): King bed, blackout curtains, smart TV, walk-in closet, ensuite full bath.

Second Bedroom (3rd floor): Queen bed, blackout curtains, smart TV, walk-in closet, its own full ensuite bath access.

Pullout Sofa (1st floor): In comfortable living area, with smart TV, adjacent half bath, blackout curtains for privacy.

☆☆ BATHROOMS ☆☆

You’ll have 2 full bathrooms (both richly appointed with fluffy towels, body wash, shampoo, conditioner, and essentials) and 2 additional half baths for guests, so no waiting in line during busy mornings or after late nights.

☆☆ KITCHEN & RELAXING AREAS ☆☆

The heart of the home is a modern, fully stocked kitchen, high-end appliances, cookware, utensils, dining settings, plus both Nespresso and Keurig for your preferred brew. The main living area (on the second floor) blends comfort and style with plush seating, smart TV, and easy flow to the patio. It’s an ideal setting for relaxing, chatting, or gearing up before a concert or game. There is also an additional living area on the first floor equipped with a half-bath, smart tv, and dedicated workspace.

☆☆ OUTSIDE SPACE ☆☆

Step outside to your private patio overlooking the Distillery District, draped in bistro lights and outfitted with seating, perfect for morning coffee or evening wind-downs. Parking includes your driveway spot, shared complex parking, and additional on-street options for extra flexibility.

★☆ Book Today & Let Us Take Care Of You ☆★

Don’t miss out on this upscale, convenient getaway in one of Lexington’s most vibrant neighborhoods. Book now and relax. We’ll take care of the rest!

Property is a 3-story townhome, stairs are required to access 2 of the bedrooms.

Permit #: STR-26-000007

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 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 Registration Number Permit #: STR-26-000007
Property # 20202140
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
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

Lexington

Distillery District, a neighbourhood in Lexington, is home to this holiday home. Hamburg Place and Victorian Square Mall are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Raven Run Nature Sanctuary and Triangle Park. Looking to enjoy an event or a game while in town? See what's going on at Keeneland Racing Course, or consider a night out at The Kentucky Castle.
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Map
Lexington, KY

What's nearby

  • Lexington Brewing & Distilling Co. - 2 min walk - 0.2 km
  • Rupp Arena - 8 min walk - 0.7 km
  • Lexington Convention Center - 14 min walk - 1.2 km
  • Lexington Opera House - 14 min walk - 1.2 km
  • University of Kentucky - 15 min walk - 1.3 km

Getting around

  • Lexington, KY (LEX-Blue Grass) - 12 min drive

Restaurants

  • ‪Country Boy Brewing - ‬17 min walk
  • ‪Lexington Brewing & Distilling Co. - ‬8 min walk
  • ‪Triangle Park Cafe - ‬15 min walk
  • ‪Chaotic Good: Coffee, Comics And Games - ‬18 min walk
  • ‪Pies & Pints - Lexington, KY - ‬16 min walk

Frequently asked questions

Is Winners Circle - 2BR - Patio-Garage - Walk to Rupp pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Winners Circle - 2BR - Patio-Garage - Walk to Rupp?

As of 11 Jun, 2026, prices found for a 1-night stay for 2 adults at Winners Circle - 2BR - Patio-Garage - Walk to Rupp on 14 Jun, 2026 start from S$574, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Winners Circle - 2BR - Patio-Garage - Walk to Rupp?

On-site parking is available at the property.

What time is check-in at Winners Circle - 2BR - Patio-Garage - Walk to Rupp?

Check-in begins at 4:00 PM.

What time is check-out at Winners Circle - 2BR - Patio-Garage - Walk to Rupp?

Checkout is at 11:00 AM.

Where is Winners Circle - 2BR - Patio-Garage - Walk to Rupp located?

Located in Distillery District, this holiday home is within 1 mile (2 km) of Lexington Brewing & Distilling Co., University of Kentucky and Lexington Convention Center. Rupp Arena and Mary Todd Lincoln 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. 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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Gary R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was nice. We intend on staying again. The location was good.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Elizabeth

Liked: Cleanliness, check-in, communication, listing accuracy
The location was great for our trip. The property was very clean and nicely furnished, and the horse racing touches were well done. We enjoyed sitting on the upstairs patio in the evenings. If you are a light sleeper bring earplugs, as the trains and traffic noise took a few nights to get used to. We were fine with it, but be aware that the two sets of stairs are steep. We will definitely stay again and recommend to others
Stayed 4 nights in May 2026
Verified

10/10 Excellent

jill s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved our stay! Very spacious, immaculate, and beautiful decor. We enjoyed an easy walk to the distillery district. Very well set up and stocked for a perfect family weekend. Overall, a very welcoming experience. Easily a 10/10.
Stayed 2 nights in Oct 2025

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