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Upscale Kentucky Bourbon Trail & Close to Louisville

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your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Upscale Kentucky Bourbon Trail & Close to Louisville

Interior
2 bedrooms, desk, iron/ironing board, WiFi
TV
Interior
Property grounds

Reviews

9.8 out of 10

Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 41195 sq ft

Popular amenities

  • Parking available
  • Washer
  • Barbecue grill
  • Outdoor Space
  • Kitchen
  • Air conditioning

Explore the area

Map
Shelbyville, KY
  • UofL Health - Shelbyville Hospital
    17 min walk
  • Weissinger Hills Golf Course
    6 min drive
  • Jeptha Creed Distillery
    8 min drive
  • Frankfort, KY (FFT-Capital City)
    23 min drive

Room options

Similar properties

About the neighborhood

Shelbyville

Located in Shelbyville, this vacation home is in a rural location, within a 15-minute drive of Jeptha Creed Distillery and The Outlet Shoppes of the Bluegrass. .This vacation home is 27.3 mi (43.9 km) from Buffalo Trace Distillery and 29.5 mi (47.6 km) from Louisville Mega Cavern.

What's nearby

  • UofL Health - Shelbyville Hospital - 17 min walk
  • Jeptha Creed Distillery - 8 min drive
  • The Outlet Shoppes of the Bluegrass - 11 min drive
  • Valhalla Golf Club - 22 min drive
  • Buffalo Trace Distillery - 31 min drive

Getting around

  • Louisville, KY (LOU-Bowman Field) - 30 min drive

Restaurants

  • ‪McDonald's - ‬2 min drive
  • ‪Wings and Rings - ‬4 min drive
  • ‪Cracker Barrel - ‬4 min drive
  • ‪Dairy Queen - ‬19 min walk
  • ‪White Castle - ‬5 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Upscale Kentucky Bourbon Trail & Close to Louisville

Welcome to The Oak, an upscale first floor 2-bedroom, 2-bath retreat in the heart of Kentucky's Bourbon Trail. Located in historic downtown Shelbyville, this 1909 house has been painstakingly restored to highlight its charm. Enjoy tasteful décor (including local artwork by the 148th Kentucky Derby artist), plush furnishings, and a fully-equipped kitchen. Relax on the patio or enjoy boardgames after a day at the famous bourbon distilleries and horse farms. Walk to dinner and shops. Retreat to elegant bedrooms with premium linens. The Oak offers the perfect base for bourbon and horse enthusiasts. Book now for a memorable experience of luxury and comfort.

The Oak is located at 1029 Main Street. Experience the smalltown charm of historic Shelbyville Kentucky, where you can walk to local boutique shops and restaurants. Shelbyville is the Saddlebred Capital of the World and boasts a central location between Louisville, Lexington and Bardstown in the heart of the Kentucky Bourbon Trail. Connect with locals, embrace the culture, and create memorable moments at The Oak in Shelbyville, KY.


The Property

We offer 2 queen bedrooms and 2 full bathrooms with tiled showers, 1 of which is ensuite.

We offer a living space complete with a living room, a smart TV and a fully stocked kitchen.

We also offer a covered patio and grill for your evening BBQ. (It is shared with our connected property the Copper)

Kitchen-The fully stocked kitchen is ready for guests to eat, drink and be merry. Each has an attached dining space for 4

Coffee- A Keurig Coffee machine is provided along with enough pods, sweeteners, and creamer to get you started.

Enjoy cards and boards games with friends and family for added enjoyment

Two private off street parking spaces are available at the rear of the property.

Guest access
Guests will have full access to the property other than the garage area. Please note that the Oak is a 1st Story Unit.

Other Items of interest
Signature cocktail welcome kit included featuring local bitters and mixer (BYOB- Bring your own Bourbon)
Bathroom toiletries provided (shampoo, conditioner, body wash, lotion, bar soap)
Contactless check in and check out through our smart lock system


If your visit includes the bourbon trail, please make your tour reservations well in advance as spaces fill up fast.

Within a 50 mile radius of The Oak you'll find dozens of the most famous bourbon distilleries offering unique flavors and experiences (and you'll enjoy Kentucky's scenic countryside and horse farms along the way).

Bulleit Distilling Co. (4 mi)
Jeptha Creed Distillery (4.8 mi)
Whiskey Thief Distilling Co. (14 mi)
Heaven's Door Distillery (coming Sept. 2023) (14 mi)
Kentucky Artisan Distillery (20 mi)
Buffalo Trace Distillery (23 mi.)
Wild Turkey Distillery (26 mi)
Castle & Key Distillery (28 mi)
Four Roses Distillery (29 mi)
Woodford Reserve Distillery (30 mi)
Rabbit Hole Distillery (30 mi)
Angel's Envy Distillery (31 mi)
Old Forester Distilling Co. (32 mi)
Michter's Fort Nelson Distillery (32 mi)
Evan Williams Experience (32 mi)
Peerless Distillery (32 mi)
Copper & Kings (34 mi)
Stitzel-Weller Distillery (37 mi)
Bardstown Bourbon Co. (40 mi)
Lux Row Distillers (41 mi)
Heaven Hill Distillery (42 mi)
Willett Distillery (43 mi)
RD1 Spirits (44 mi)
Preservation Distillery (44 mi)
Jim Beam Distilling Co. (46 mi)


Other Kentucky experiences you won't want to miss:
Shelby Co. Fairgrounds and Horse Show (0.8 mi)
Valhalla Golf Course (14 mi)
Kentucky's historic Capitol (20 mi)
Churchill Downs & Kentucky Derby Museum (31 mi)
Belle of Louisville Riverboat (31 mi)
Louisville Slugger Museum (32 mi)
Keeneland Racetrack (40 mi)
Kentucky Horse Park (46 mi)
No candles are allowed to be burned in the home.
No one other than guests within the reservation are permitted to stay at the home.
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a desk and a microwave.
This smoke-free vacation home offers games.
Guests will find features like internet access and onsite parking.

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • TV

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,195 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

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

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
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 is also known as

170703

Upscale Kentucky Bourbon Trail & Close to Louisville Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 6 out of 7 reviews" "
Rating 8 - Good. 1 out of 7 reviews" "
Rating 6 - Okay. 0 out of 7 reviews" "
Rating 4 - Poor. 0 out of 7 reviews" "
Rating 2 - Terrible. 0 out of 7 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Beth G.

Liked: Cleanliness
Our stay was perfect
Everything about our getaway was perfect. We arrived to the house around 9 and the keyless entry was flawless. The house was exactly as the pictures described and was perfect for two couples. The decor of the home was nicely created and felt very homey. We spent most of our time on the Bourbon Trail and loved the location so we could get to where we were going in about 30 to 45 minutes. Buffalo Trace was a daily stop and was a 30 minute drive. We’d definitely recommend this home.
Stayed 4 nights in Dec 2024

10/10 Excellent

Sharla W.

Liked: Cleanliness
Great Location
If you are looking for a place to stay while checking out the Bourbon Trail, this is an ideal location. Quiet and very clean. Easy access to the different regions of the Bourbon Trail. We highly recommend.
Stayed 3 nights in Aug 2024

10/10 Excellent

Verified traveler

Liked: Cleanliness
Ease on the Bourbon Trail
What a beautiful property. Love the dark makeup towels provided and the mixed drink suggestion. The convenience was great. In between Louisville and Lexington. Nice small town to explore. Would definitely go again. Thanks for experience.
Stayed 3 nights in Jun 2024

10/10 Excellent

mary anne a.

Liked: Cleanliness
Nice, clean rental
The Oak is on the bottom floor of a 2 story STR. It was very clean, with a spacious and well-stocked kitchen and dining area. The living room was cozy as were the 2 bedrooms. This is a very old building and we could hear the people above us enjoying themselves when we were in the living room. This property is an easy walk to downtown and restaurants. It is also right next door to a pizza shop and convenience store. We did need to contact management over a few, small issues that were very quickly addressed and corrected.
Stayed 5 nights in May 2024

10/10 Excellent

Kelcey S.

Liked: Cleanliness
Bourbon Tour Stay
Loved this stay - We took a trip to celebrate a couple of 30th birthday's on the Bourbon Tour and this was the perfect house for it. Very great location to the distilleries, restaurants, and coffee shops. The place was very clean and beautifully updated. The managers stayed in contact with us during our stay, but we never needed anything as it was ready for us when we arrived!
Stayed 3 nights in Sep 2023

10/10 Excellent

Doris T., Richmond VA

Liked: Cleanliness
Great Location
Very convenient location in Shelbyville-- easy drive into Louisville and Frankfort.
Stayed 6 nights in Aug 2023

8/10 Good

Danielle H.

Liked: Cleanliness
Bourbon Trail
This property was a great homebase for our stops on the Bourbon Trail. Nicely remodeled and well appointed with all the basics. Neighborhood can be occasionally loud as the fire station is a block away.
Stayed 3 nights in Jul 2023