
Holiday rentals near The Kentucky Theater
We found 668 holiday rentals — enter your dates for availability
Select the perfect holiday home within easy reach of The Kentucky Theater. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as air conditioning and cable TV. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - The Kentucky Theater
Showing deals for:14 Nov - 21 Nov
Image gallery for Handcrafted Rustic Cabin on the Bourbon Trail

1010 out of 10 rating
Exceptional
(17 reviews)
Handcrafted Rustic Cabin on the Bourbon Trail
Versailles, KY
8% off
Price is S$1,817
S$1,817
S$260 per night
includes taxes & fees
Image gallery for 1840 Historic Antebellum Estate in the heart of the Bluegrass

1010 out of 10 rating
Exceptional
(17 reviews)
1840 Historic Antebellum Estate in the heart of the Bluegrass
Paris, KY
8% off
Price is S$21,200
S$21,200
S$3,029 per night
includes taxes & fees
Image gallery for Quiet, Comfortable Cottage

9.89.8 out of 10 rating
Exceptional
(92 reviews)
Quiet, Comfortable Cottage
Versailles, KY
12% off
Price is S$1,870
S$1,870
S$267 per night
includes taxes & fees
Image gallery for HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm

1010 out of 10 rating
Exceptional
(20 reviews)
HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm
Georgetown, KY
8% off
Price is S$14,112
S$14,112
S$2,016 per night
includes taxes & fees
Image gallery for Scenic Stillwater Retreat in rural KY Horse Country, WiFi/AC, Fishing/Canoeing

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Scenic Stillwater Retreat in rural KY Horse Country, WiFi/AC, Fishing/Canoeing
Paris, KY
8% off
Price is S$2,877
S$2,877
S$411 per night
includes taxes & fees
Image gallery for New 2-bedroom farmhouse on 23 acres of pasture, part of a working horse farm.

1010 out of 10 rating
Exceptional
(23 reviews)
New 2-bedroom farmhouse on 23 acres of pasture, part of a working horse farm.
Cynthiana, KY
13% off
Price is S$2,278
S$2,278
S$325 per night
includes taxes & fees
Image gallery for Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.

9.89.8 out of 10 rating
Exceptional
(26 reviews)
Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.
Lexington, KY
8% off
Price is S$3,006
S$3,006
S$429 per night
includes taxes & fees
Image gallery for Happy Moo's Fink Family Farm, where cows & guests are free to enjoy our 50 acres

1010 out of 10 rating
Exceptional
(6 reviews)
Happy Moo's Fink Family Farm, where cows & guests are free to enjoy our 50 acres
Versailles, KY
23% off
Price is S$5,490
S$5,490
S$784 per night
includes taxes & fees
Image gallery for Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport

1010 out of 10 rating
Exceptional
(57 reviews)
Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport
Versailles, KY
8% off
Price is S$7,095
S$7,095
S$1,014 per night
includes taxes & fees
Image gallery for The Bourbon Sanctuary

9.89.8 out of 10 rating
Exceptional
(18 reviews)
The Bourbon Sanctuary
Frankfort, KY
8% off
Price is S$1,564
S$1,564
S$223 per night
includes taxes & fees
Image gallery for Cozy updated home mins to Keeneland & Lexington. Championship Golf Course Views

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cozy updated home mins to Keeneland & Lexington. Championship Golf Course Views
Nicholasville, KY
8% off
Price is S$6,298
S$6,298
S$900 per night
includes taxes & fees
Image gallery for Peaceful Chevy Chase Retreat

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Peaceful Chevy Chase Retreat
Lexington, KY
8% off
Price is S$5,377
S$5,377
S$768 per night
includes taxes & fees
Image gallery for Riverside Roost -bourbon themed waterfront home

1010 out of 10 rating
Exceptional
(13 reviews)
Riverside Roost -bourbon themed waterfront home
Versailles, KY
16% off
Price is S$1,817
S$1,817
S$260 per night
includes taxes & fees
Image gallery for Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!

1010 out of 10 rating
Exceptional
(15 reviews)
Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!
Nicholasville, KY
11% off
Price is S$8,155
S$8,155
S$1,165 per night
includes taxes & fees
Image gallery for Springside BoHo Getaway

1010 out of 10 rating
Exceptional
(46 reviews)
Springside BoHo Getaway
Georgetown, KY
8% off
Price is S$1,798
S$1,798
S$257 per night
includes taxes & fees
Image gallery for Beautiful farm stay apartment, rural Georgetown KY

9.89.8 out of 10 rating
Exceptional
(32 reviews)
Beautiful farm stay apartment, rural Georgetown KY
Georgetown, KY
8% off
Price is S$1,186
S$1,186
S$169 per night
includes taxes & fees
Image gallery for Unbeatable location for the best experiences in Central Kentucky

1010 out of 10 rating
Exceptional
(10 reviews)
Unbeatable location for the best experiences in Central Kentucky
Lexington, KY
9% off
Price is S$3,833
S$3,833
S$548 per night
includes taxes & fees
Image gallery for Bourbon n Horses themed 3B/2Ba home in beautiful Chevy Chase neighborhood!

1010 out of 10 rating
Exceptional
(34 reviews)
Bourbon n Horses themed 3B/2Ba home in beautiful Chevy Chase neighborhood!
Lexington, KY
8% off
Price is S$3,158
S$3,158
S$451 per night
includes taxes & fees
Image gallery for 🏇🏼Equestrian & Bourbon Central🥃 👑The Kingston👑 Near Fasig-Tipton & KYSHP🐴

1010 out of 10 rating
Exceptional
(16 reviews)
🏇🏼Equestrian & Bourbon Central🥃 👑The Kingston👑 Near Fasig-Tipton & KYSHP🐴
Lexington, KY
6% off
Price is S$2,754
S$2,754
S$393 per night
includes taxes & fees
Image gallery for Welcome Hall 5 bedroom 1880’s home on 55 acres

9.89.8 out of 10 rating
Exceptional
(28 reviews)
Welcome Hall 5 bedroom 1880’s home on 55 acres
Paris, KY
15% off
Price is S$4,457
S$4,457
S$637 per night
includes taxes & fees
Image gallery for Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown

1010 out of 10 rating
Exceptional
(24 reviews)
Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
Georgetown, KY
8% off
Price is S$2,511
S$2,511
S$359 per night
includes taxes & fees
Image gallery for This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key

1010 out of 10 rating
Exceptional
(11 reviews)
This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key
Nicholasville, KY
8% off
Price is S$9,588
S$9,588
S$1,370 per night
includes taxes & fees
Image gallery for Great Location | Patio | Grill | Tempurpedic Beds

9.89.8 out of 10 rating
Exceptional
(29 reviews)
Great Location | Patio | Grill | Tempurpedic Beds
Lexington, KY
6% off
Price is S$1,741
S$1,741
S$249 per night
includes taxes & fees
Image gallery for Greenwood Farm log cabin close to the Bourbon Trail and Keeneland

1010 out of 10 rating
Exceptional
(29 reviews)
Greenwood Farm log cabin close to the Bourbon Trail and Keeneland
Versailles, KY
8% off
Price is S$2,295
S$2,295
S$328 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Kentucky Theater
Treetops Solar Sanctuary
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
77 reviews(77 reviews)
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Sleeps 13 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Nature Escape! Unit Near Attractions in GuestHouse Lexington, Parking, Pool!
Sleeps 4 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
6 reviews(6 reviews)
1840 Historic Antebellum Estate in the heart of the Bluegrass
Sleeps 20 · 8 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
12acre Villa right by Keeneland-Keene Creek Estate 10,000sqft
Sleeps 19 · 7 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Pool | Hot Tub | Covered Porch | Patio | Game Room
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
115 reviews(115 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value