Verified
10/10 Excellent
jill s.
19 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
jill s.
Stayed 2 nights in Oct 2025
Entire home
Winners Circle - 2BR - Patio-Garage - Walk to Rupp
Photo gallery for Winners Circle - 2BR - Patio-Garage - Walk to Rupp
Close to Red Mile Racetrack and University of Kentucky, Winners Circle - 2BR - Patio-Garage - Walk to Rupp provides amenities like laundry facilities. Stay connected with free in-room WiFi.
Reviews
1010 out of 10
Exceptional
Entire home
2 bedrooms3 bathrooms139 sq m
Popular amenities
- Kitchen
- Washer
- Dryer
- Free WiFi
- Air conditioning
- Outdoor Space
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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
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 transportation
- Onsite parking options include a garage
Kitchen
- Blender
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Electric kettle
- Ice maker
- Kitchen island
- Lobster/crab pot
- Microwave
- Oven
- Paper towels
- Refrigerator
- Stovetop
- 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 elevator
- Smoking not allowed
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
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
We should mention
This property does not have elevators
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?
Onsite 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?
Check-out is at 11:00 AM.
Where is Winners Circle - 2BR - Patio-Garage - Walk to Rupp located?
Located in Distillery District, this vacation 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 travelers 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.
Rating 10 - Excellent. 3 out of 3 reviews
10 - Excellent
3
Rating 8 - Good. 0 out of 3 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 3 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 3 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 3 reviews
2 - Terrible
0
10
Cleanliness
10
Location
Reviews
Verified
10/10 Excellent
Elizabeth
17 May 2026
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
Elizabeth
Stayed 4 nights in May 2026
Verified
10/10 Excellent
Gary R.
29 April 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was nice. We intend on staying again. The location was good.
Gary R.
Stayed 3 nights in Apr 2026