Photo by Abby Fieldhouse

Vacation Rentals in Anderson County

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Vacation Rentals in Anderson County

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Exterior detail

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

10.0 out of 10, Exceptional, (114)
"Us and another couple came for a bourbon weekend. It was the perfect location between Bardstown and Frankfort. The location was a bit hard to find the first time especially at night, but the host gave great directions!"
The price is ￥22,079
￥32,940 total
includes taxes & fees
Nov 3 - Nov 4
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
Exterior

High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20

10.0 out of 10, Exceptional, (5)
"Remote relaxation"
The price is ￥176,628
￥304,566 total
includes taxes & fees
Oct 15 - Oct 16
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20
Peaceful Retreat on the Bourbon Trail
Interior

Peaceful Retreat on the Bourbon Trail

9.8 out of 10, Exceptional, (7)
"The home is clean, very clean. The property is beautiful. The manager is friendly and gives you space. It may be the best equipped home I've rented so far. Everything you could need is there it seems. Really appreciated the little extras as well. Will be recommending this place to anyone who i know is going to the bourbon trail. "
The price is ￥22,052
￥41,488 total
includes taxes & fees
Oct 9 - Oct 10
Peaceful Retreat on the Bourbon Trail
Lakefront Home Close to Bourbon Trail--Dog friendly!
Property grounds

Lakefront Home Close to Bourbon Trail--Dog friendly!

9.8 out of 10, Exceptional, (79)
"Fantastic house and location! Close to the bourbon trail and cannot beat a morning coffee over looking the lake!"
Lakefront Home Close to Bourbon Trail--Dog friendly!
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!
Property grounds

KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

9.8 out of 10, Exceptional, (126)
"The location and amenities were perfect for us. We were in town for the bourbon trail and it was a perfect location. Being able to come back and sit by the fire, fish or sit in the hot tub was a perfect end to each day. Sherry was very quick to respond when we had questions about the house or the area. We will definitely stay here when we come back. Highly recommend!!!"
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
Exterior

Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28

10.0 out of 10, Exceptional, (13)
"We had a remarkable time enjoying the entire property. Highly recommend! "
Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

8.8 out of 10, Excellent, (34)
"Enjoyed our stay and location, would return in future "
The price is ￥12,806
￥27,997 total
includes taxes & fees
Oct 27 - Oct 28
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Cecil's Cozy Cottage
Fridge, microwave, oven, stovetop

Cecil's Cozy Cottage

9.4 out of 10, Exceptional, (60)
"Nicely updated, clean and cozy. "
The price is ￥16,927
￥32,118 total
includes taxes & fees
Oct 27 - Oct 28
Cecil's Cozy Cottage
Unique Cabin on the Beechfork River, nestled in the heart of the Bourbon Trail
Terrace/patio

Unique Cabin on the Beechfork River, nestled in the heart of the Bourbon Trail

2.0 star property
10.0 out of 10, Exceptional, (33)
"Clean and very cute place plenty of room for two couples"
Unique Cabin on the Beechfork River, nestled in the heart of the Bourbon Trail
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.

2.0 star property
10.0 out of 10, Exceptional, (8)
"We absolutely loved our stay! The property was super nice and very spacious, it was in a perfect location to reach anywhere in downtown Lex. Will definitely book again!"
The price is ￥29,438
￥50,255 total
includes taxes & fees
Oct 27 - Oct 28
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!
Outdoor dining

Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!

10.0 out of 10, Exceptional, (21)
"It's a wonderful house for a family visit, and its very convenient to Keeneland. "
The price is ￥40,271
￥139,481 total
includes taxes & fees
Oct 8 - Oct 9
Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!
Stay in a historic Early 1800s Guest House!
Exterior

Stay in a historic Early 1800s Guest House!

10.0 out of 10, Exceptional, (108)
"Great location and cottage! We loved it!"
The price is ￥16,927
￥29,694 total
includes taxes & fees
Oct 29 - Oct 30
Stay in a historic Early 1800s Guest House!
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Fridge, coffee/tea maker, cookware/dishes/utensils

This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.

9.2 out of 10, Wonderful, (70)
"We gambled n we won"
The price is ￥21,343
￥39,152 total
includes taxes & fees
Oct 27 - Oct 28
This house is a 3 bedroom(s), 2 bathrooms, located in Lexington, KY.
Charming 2-bedroom townhome with WiFi, AC in Lexington
Property grounds

Charming 2-bedroom townhome with WiFi, AC in Lexington

Charming 2-bedroom townhome with WiFi, AC in Lexington
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Property grounds

Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

10.0 out of 10, Exceptional, (145)
"This is our third time staying here! We love the location, the quaintness of the place and the ease of check in and check out! Looking forward to staying here again! "
The price is ￥14,570
￥24,600 total
includes taxes & fees
Oct 7 - Oct 8
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Exterior

Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

9.6 out of 10, Exceptional, (235)
"The place was awesome and suited the bachelor party perfectly!"
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
Terrace/patio

Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.

10.0 out of 10, Exceptional, (92)
"5 of us stayed at the property. Excellent all around; and in a perfect location"
Spacious family Lodge with solar heated pool, hot tub, fire pit and EV charger.
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Fridge, microwave, oven, stovetop

This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

2.0 star property
9.4 out of 10, Exceptional, (10)
"Great location and huge place. Gorg windows and high ceilings. I stayed here for a friends wedding and loved it. Will stay again next time I’m in town! "
The price is ￥16,927
￥32,291 total
includes taxes & fees
Oct 8 - Oct 9
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Location, Location, Location
Fridge, microwave, oven, stovetop

Location, Location, Location

9.2 out of 10, Wonderful, (62)
"House was cute and great location in downtown Lexington! "
The price is ￥16,191
￥31,382 total
includes taxes & fees
Oct 26 - Oct 27
Location, Location, Location
Bourbon on Broadway
Smart TV

Bourbon on Broadway

2.0 star property
10.0 out of 10, Exceptional, (15)
" wanted to visit. Just a nice place to stay big enough for taking Really enjoyed it. "
The price is ￥20,607
￥37,578 total
includes taxes & fees
Oct 5 - Oct 6
Bourbon on Broadway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anderson County Hotel Reviews

Distill-Inn

Distill-Inn

10/10 Excellent
"Small and convenient. Enjoyed friendly manager/bartender at their Bourbon Bar."
William 1-night trip
Posted 2 days ago
Distill-Inn

Find out more about Anderson County

Find out more about Anderson County

Vacation Apartments in Anderson County

Search for Vacation rentals in Anderson County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Anderson County using one of the methods below:

  • View our selection of featured Vacation rentals in Anderson County
  • Use the map to find apartments and other Vacation homes in the Anderson County neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Anderson County while they last

Look no further and take a look at our great range of rental properties in Anderson County!