
Holiday rentals near Legacy Trail
We found 680 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Legacy Trail that can be your home away from home. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Legacy Trail
Showing deals for:19 Sept - 26 Sept
Image gallery for Botherum Carriage House, Garden Lovers Delight

1010 out of 10 rating
Exceptional
(10 reviews)
Botherum Carriage House, Garden Lovers Delight
Lexington, KY
8% off
Price is NZ$16,384
NZ$16,384
NZ$2,341 per night
includes taxes & fees
Image gallery for Historical Villa w/hot tub-1block from Rupp

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Historical Villa w/hot tub-1block from Rupp
Lexington, KY
8% off
Price is NZ$17,348
NZ$17,348
NZ$2,478 per night
includes taxes & fees
Image gallery for Welcome to "The Spot" Southland/6 Miles to Keeneland!

9.49.4 out of 10 rating
Exceptional
(24 reviews)
Welcome to "The Spot" Southland/6 Miles to Keeneland!
Lexington, KY
8% off
Price is NZ$4,952
NZ$4,952
NZ$707 per night
includes taxes & fees
Image gallery for World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail

9.89.8 out of 10 rating
Exceptional
(92 reviews)
World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail
Lexington, KY
16% off
Price is NZ$5,286
NZ$5,286
NZ$755 per night
includes taxes & fees
Image gallery for Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath

1010 out of 10 rating
Exceptional
(94 reviews)
Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath
Nicholasville, KY
8% off
Price is NZ$2,425
NZ$2,425
NZ$346 per night
includes taxes & fees
Image gallery for "The Lynn" MODERN URBAN STAY w/ Backyard

1010 out of 10 rating
Exceptional
(15 reviews)
"The Lynn" MODERN URBAN STAY w/ Backyard
Lexington, KY
8% off
Price is NZ$3,313
NZ$3,313
NZ$473 per night
includes taxes & fees
Image gallery for Pool | Hot Tub | Covered Porch | Patio | Game Room

9.89.8 out of 10 rating
Exceptional
(110 reviews)
Pool | Hot Tub | Covered Porch | Patio | Game Room
Lexington, KY
7% off
Price is NZ$10,011
NZ$10,011
NZ$1,430 per night
includes taxes & fees
Image gallery for Bourbon Hous - 7 Bdrms, Bar, Billiards, Downtown Lexington

1010 out of 10 rating
Exceptional
(14 reviews)
Bourbon Hous - 7 Bdrms, Bar, Billiards, Downtown Lexington
Lexington, KY
8% off
Price is NZ$20,594
NZ$20,594
NZ$2,942 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
(56 reviews)
Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport
Versailles, KY
8% off
Price is NZ$9,128
NZ$9,128
NZ$1,304 per night
includes taxes & fees
Image gallery for Springside Equine Getaway

1010 out of 10 rating
Exceptional
(10 reviews)
Springside Equine Getaway
Georgetown, KY
8% off
Price is NZ$2,245
NZ$2,245
NZ$321 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 NZ$17,690
NZ$17,690
NZ$2,527 per night
includes taxes & fees
Image gallery for Hot Tub | Great Location | Patio | Grill | Ping Pong

1010 out of 10 rating
Exceptional
(58 reviews)
Hot Tub | Great Location | Patio | Grill | Ping Pong
Lexington, Kentucky
7% off
Price is NZ$6,801
NZ$6,801
NZ$972 per night
includes taxes & fees
Image gallery for "The Meridian" Modern Stay near Downtown / Airport

9.89.8 out of 10 rating
Exceptional
(27 reviews)
"The Meridian" Modern Stay near Downtown / Airport
Lexington, KY
8% off
Price is NZ$3,869
NZ$3,869
NZ$553 per night
includes taxes & fees
Image gallery for Kentucky Dream! 4BR, 3BA, 2Car-G/Covered Backyard Stage, 1-Mile from Rupp!

1010 out of 10 rating
Exceptional
(8 reviews)
Kentucky Dream! 4BR, 3BA, 2Car-G/Covered Backyard Stage, 1-Mile from Rupp!
Lexington, KY
7% off
Price is NZ$8,864
NZ$8,864
NZ$1,266 per night
includes taxes & fees
Image gallery for Historic Paris Livery Home of Kentucky's Covered Bridge Tour

8.68.6 out of 10 rating
Excellent
(7 reviews)
Historic Paris Livery Home of Kentucky's Covered Bridge Tour
Paris, KY
8% off
Price is NZ$2,503
NZ$2,503
NZ$358 per night
includes taxes & fees
Image gallery for Modern comfort within walking distance from UKY, Kroger Field, & Chevy Chase.

1010 out of 10 rating
Exceptional
(6 reviews)
Modern comfort within walking distance from UKY, Kroger Field, & Chevy Chase.
Lexington, KY
8% off
Price is NZ$11,202
NZ$11,202
NZ$1,600 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
(19 reviews)
New 2-bedroom farmhouse on 23 acres of pasture, part of a working horse farm.
Cynthiana, KY
13% off
Price is NZ$3,150
NZ$3,150
NZ$450 per night
includes taxes & fees
Image gallery for Brick Hous - Downtown Lexington

1010 out of 10 rating
Exceptional
(6 reviews)
Brick Hous - Downtown Lexington
Lexington, KY
8% off
Price is NZ$16,943
NZ$16,943
NZ$2,420 per night
includes taxes & fees
Image gallery for Spacious 3 BR w/ King Suite + Patio Off Interstate

9.89.8 out of 10 rating
Exceptional
(17 reviews)
Spacious 3 BR w/ King Suite + Patio Off Interstate
Lexington, KY
8% off
Price is NZ$4,166
NZ$4,166
NZ$595 per night
includes taxes & fees
Image gallery for ⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!

1010 out of 10 rating
Exceptional
(69 reviews)
⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!
Lexington, KY
11% off
Price is NZ$3,282
NZ$3,282
NZ$469 per night
includes taxes & fees
Image gallery for Hot Tub | Great Location | King Beds | Grill & Patio

1010 out of 10 rating
Exceptional
(76 reviews)
Hot Tub | Great Location | King Beds | Grill & Patio
Lexington, Kentucky
7% off
Price is NZ$6,499
NZ$6,499
NZ$928 per night
includes taxes & fees
Image gallery for Welcome to “The Spot” - North Limestone/Downtown!

9.89.8 out of 10 rating
Exceptional
(32 reviews)
Welcome to “The Spot” - North Limestone/Downtown!
Lexington, KY
11% off
Price is NZ$3,316
NZ$3,316
NZ$474 per night
includes taxes & fees
Image gallery for Located in Georgetown, KY, close to Toyota, Kentucky Horse Park, Lexington, KY

9.69.6 out of 10 rating
Exceptional
(7 reviews)
Located in Georgetown, KY, close to Toyota, Kentucky Horse Park, Lexington, KY
Georgetown, KY
16% off
Price is NZ$3,007
NZ$3,007
NZ$430 per night
includes taxes & fees
Image gallery for Minutes to Keeneland/Airport/UK & more!

1010 out of 10 rating
Exceptional
(13 reviews)
Minutes to Keeneland/Airport/UK & more!
Lexington, KY
8% off
Price is NZ$3,418
NZ$3,418
NZ$488 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Legacy Trail
Charming 3-bedroom Escape Haven in Lexington/5 mi from airport/4.3mi from H.Park
Sleeps 8 · 3 bedrooms · 2+ bathrooms
6.86.8 out of 10
3 reviews(3 reviews)
Historic Downtown Morgan Street Apartment - Pet Friendly!
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Comfort and Convenience! Free Breakfast, Free Parking, Close to Loudoun House
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
266 reviews(266 reviews)
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Sleeps 6 · 3 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Quiet, Comfortable Cottage
Sleeps 8 · 2 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
89 reviews(89 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