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

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Fridge, microwave, oven, stovetop - Winners Circle - 2BR - Patio-Garage - Walk to Rupp (Lexington)
Outdoor dining - Winners Circle - 2BR - Patio-Garage - Walk to Rupp (Lexington)
Exterior - Winners Circle - 2BR - Patio-Garage - Walk to Rupp (Lexington)
2 bedrooms, desk, iron/ironing board, travel cot - Winners Circle - 2BR - Patio-Garage - Walk to Rupp (Lexington)
Interior - Winners Circle - 2BR - Patio-Garage - Walk to Rupp (Lexington)
Close to Red Mile Racetrack and University of Kentucky, Winners Circle - 2BR - Patio-Garage - Walk to Rupp provides amenities such as laundry facilities. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms3 bathrooms1495 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Add dates for prices

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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • No lift
  • Smoke-free property

Services and conveniences

  • Change of bedsheets (on request)
  • Change of towels on request
  • Housekeeping on request
  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • At least 80% lighting from LEDs
  • Bed sheets changed on request
  • Housekeeping (on request)
  • Towels (changed on request)
  • Unit size: 1,495 square feet
  • Water-efficient showers

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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age - 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number Permit #: STR-26-000007
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

We should mention

This property does not have any lifts

Frequently asked questions

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

No, pets are not allowed at this property.

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 mi (2 km) of Lexington Brewing & Distilling Co. and University of Kentucky. Rupp Arena and Mary Todd Lincoln House are also within 15 minutes.

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Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

10

Location

Reviews

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
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

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