
Holiday rentals near Legacy Trail
We found 686 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:31 Oct - 7 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 NZ$2,828
NZ$2,828
NZ$404 per night
includes taxes & fees
Image gallery for Fully Renovated | Finished Basement | Luxury Beds | Games

1010 out of 10 rating
Exceptional
(65 reviews)
Fully Renovated | Finished Basement | Luxury Beds | Games
Lexington, KY
7% off
Price is NZ$4,676
NZ$4,676
NZ$668 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 NZ$9,426
NZ$9,426
NZ$1,347 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 NZ$4,045
NZ$4,045
NZ$578 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 NZ$1,568
NZ$1,568
NZ$224 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 NZ$7,214
NZ$7,214
NZ$1,031 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom in Lexington

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Cozy 1-bedroom in Lexington
Lexington, KY
7% off
Price is NZ$1,534
NZ$1,534
NZ$219 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 NZ$3,017
NZ$3,017
NZ$431 per night
includes taxes & fees
Image gallery for Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!

9.49.4 out of 10 rating
Exceptional
(45 reviews)
Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!
Lexington, KY
16% off
Price is NZ$1,739
NZ$1,739
NZ$248 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 NZ$4,880
NZ$4,880
NZ$697 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 NZ$5,312
NZ$5,312
NZ$759 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 NZ$2,474
NZ$2,474
NZ$353 per night
includes taxes & fees
Image gallery for "The Berry" Mid-Century Modern Stay w/ 3BR - UK

9.69.6 out of 10 rating
Exceptional
(10 reviews)
"The Berry" Mid-Century Modern Stay w/ 3BR - UK
Lexington, KY
8% off
Price is NZ$3,148
NZ$3,148
NZ$450 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 NZ$5,866
NZ$5,866
NZ$838 per night
includes taxes & fees
Image gallery for Pool | Hot Tub | Covered Porch | Patio | Game Room

9.89.8 out of 10 rating
Exceptional
(111 reviews)
Pool | Hot Tub | Covered Porch | Patio | Game Room
Lexington, KY
7% off
Price is NZ$11,109
NZ$11,109
NZ$1,587 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 NZ$2,856
NZ$2,856
NZ$408 per night
includes taxes & fees
Image gallery for Entire Home in Hamburg!

1010 out of 10 rating
Exceptional
(23 reviews)
Entire Home in Hamburg!
Lexington, KY
7% off
Price is NZ$2,837
NZ$2,837
NZ$405 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
5% off
Price is NZ$2,833
NZ$2,833
NZ$405 per night
includes taxes & fees
Image gallery for The River Side Lodge- With private boat dock on the KY river!

9.09.0 out of 10 rating
Wonderful
(21 reviews)
The River Side Lodge- With private boat dock on the KY river!
Harrodsburg, KY
7% off
Price is NZ$1,891
NZ$1,891
NZ$270 per night
includes taxes & fees
Image gallery for Firepit | Outdoor Deck | Great Location

1010 out of 10 rating
Exceptional
(78 reviews)
Firepit | Outdoor Deck | Great Location
Lexington, KY
7% off
Price is NZ$4,450
NZ$4,450
NZ$636 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 NZ$3,801
NZ$3,801
NZ$543 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
9% off
Price is NZ$10,329
NZ$10,329
NZ$1,476 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 NZ$3,563
NZ$3,563
NZ$509 per night
includes taxes & fees
Image gallery for 1800’s Historical Log Cabin near I-75 Interstate

9.49.4 out of 10 rating
Exceptional
(40 reviews)
1800’s Historical Log Cabin near I-75 Interstate
Lexington, KY
7% off
Price is NZ$1,877
NZ$1,877
NZ$268 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Legacy Trail
The Midland- 2 King Beds! Great Location!
Sleeps 4 · 2 bedrooms · 2+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
23 reviews(23 reviews)
‘Clara’ Just Off I-75! 2 Full Bedrooms!
Sleeps 5 · 2 bedrooms · 1 bathroom
8.48.4 out of 10
Very goodvery good
19 reviews(19 reviews)
Earl Grey - Studio Space in Downtown Lexington
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
New 2-bedroom farmhouse on 23 acres of pasture, part of a working horse farm.
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.
Sleeps 6 · 3 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 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