Holiday rentals near Castlewood Park
We found 500 holiday rentals — enter your dates for availability
Choose the right private holiday rental within close proximity to Castlewood Park. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as a garden and pool. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Castlewood Park
Showing deals for:25 Jul - 1 Aug
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$17,324
NZ$17,324
NZ$2,475 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
7% off
Price is NZ$18,270
NZ$18,270
NZ$2,610 per night
includes taxes & fees
Image gallery for Luxe Home w/Pool, Hot Tub, Game Rm, Bar-near Keeneland, UK, Brbn Trail-pets ok!
1010 out of 10 rating
Exceptional
(8 reviews)
Luxe Home w/Pool, Hot Tub, Game Rm, Bar-near Keeneland, UK, Brbn Trail-pets ok!
Nicholasville, KY
12% off
Price is NZ$15,580
NZ$15,580
NZ$2,226 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
7% off
Price is NZ$4,145
NZ$4,145
NZ$592 per night
includes taxes & fees
Image gallery for Hot Tub | Great Location | Patio | Grill | Ping Pong
1010 out of 10 rating
Exceptional
(57 reviews)
Hot Tub | Great Location | Patio | Grill | Ping Pong
Lexington, Kentucky
7% off
Price is NZ$8,977
NZ$8,977
NZ$1,282 per night
includes taxes & fees
Image gallery for "The Meridian" Modern Stay near Downtown / Airport
9.89.8 out of 10 rating
Exceptional
(25 reviews)
"The Meridian" Modern Stay near Downtown / Airport
Lexington, KY
7% off
Price is NZ$4,552
NZ$4,552
NZ$650 per night
includes taxes & fees
Image gallery for 7 Bedrooms | 6.5 Bathrooms | Hot Tub | 10 Beds
1010 out of 10 rating
Exceptional
(27 reviews)
7 Bedrooms | 6.5 Bathrooms | Hot Tub | 10 Beds
Lexington, Kentucky
7% off
Price is NZ$14,928
NZ$14,928
NZ$2,133 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$9,857
NZ$9,857
NZ$1,408 per night
includes taxes & fees
Image gallery for 527 Estrella · King Bed, entire 4 bedroom, Kentucky living
1010 out of 10 rating
Exceptional
(17 reviews)
527 Estrella · King Bed, entire 4 bedroom, Kentucky living
Lexington, KY
7% off
Price is NZ$8,217
NZ$8,217
NZ$1,174 per night
includes taxes & fees
Image gallery for ⭐️Renovated⭐️ Great Location Fire Pit - Dog Friendly - Fully Fenced - Games
1010 out of 10 rating
Exceptional
(8 reviews)
⭐️Renovated⭐️ Great Location Fire Pit - Dog Friendly - Fully Fenced - Games
Lexington, KY
7% off
Price is NZ$5,769
NZ$5,769
NZ$824 per night
includes taxes & fees
Image gallery for Upscale downtown Lexington townhome
1010 out of 10 rating
Exceptional
(51 reviews)
Upscale downtown Lexington townhome
Lexington, KY
8% off
Price is NZ$10,501
NZ$10,501
NZ$1,500 per night
includes taxes & fees
Image gallery for Welcome to “The Spot” - North Limestone/Downtown!
1010 out of 10 rating
Exceptional
(29 reviews)
Welcome to “The Spot” - North Limestone/Downtown!
Lexington, KY
10% off
Price is NZ$3,619
NZ$3,619
NZ$517 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
(16 reviews)
Spacious 3 BR w/ King Suite + Patio Off Interstate
Lexington, KY
7% off
Price is NZ$4,167
NZ$4,167
NZ$595 per night
includes taxes & fees
Image gallery for Renovated Train Station on Thoroughbred Horse Farm
1010 out of 10 rating
Exceptional
(264 reviews)
Renovated Train Station on Thoroughbred Horse Farm
Paris, KY
8% off
Price is NZ$3,121
NZ$3,121
NZ$446 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
(64 reviews)
⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!
Lexington, KY
11% off
Price is NZ$3,736
NZ$3,736
NZ$534 per night
includes taxes & fees
Image gallery for Minutes to Keeneland/Airport/UK & more!
1010 out of 10 rating
Exceptional
(8 reviews)
Minutes to Keeneland/Airport/UK & more!
Lexington, KY
7% off
Price is NZ$3,836
NZ$3,836
NZ$548 per night
includes taxes & fees
Image gallery for Cozy, Comfortable & Convenient
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Cozy, Comfortable & Convenient
Lexington, KY
6% off
Price is NZ$3,490
NZ$3,490
NZ$499 per night
includes taxes & fees
Image gallery for "The Berry" Mid-Century Modern Stay w/ 3BR - UK
9.89.8 out of 10 rating
Exceptional
(9 reviews)
"The Berry" Mid-Century Modern Stay w/ 3BR - UK
Lexington, KY
7% off
Price is NZ$3,880
NZ$3,880
NZ$554 per night
includes taxes & fees
Image gallery for Great Location | Patio | Grill | Tempurpedic Beds
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Great Location | Patio | Grill | Tempurpedic Beds
Lexington, Kentucky
7% off
Price is NZ$3,252
NZ$3,252
NZ$465 per night
includes taxes & fees
Image gallery for Great Location / Keeneland / Rupp / Fenced Yard / Games
1010 out of 10 rating
Exceptional
(13 reviews)
Great Location / Keeneland / Rupp / Fenced Yard / Games
Lexington, KY
7% off
Price is NZ$4,142
NZ$4,142
NZ$592 per night
includes taxes & fees
Image gallery for Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.
1010 out of 10 rating
Exceptional
(22 reviews)
Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.
Lexington, KY
10% off
Price is NZ$3,965
NZ$3,965
NZ$566 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
(31 reviews)
Bourbon n Horses themed 3B/2Ba home in beautiful Chevy Chase neighborhood!
Lexington, KY
7% off
Price is NZ$3,710
NZ$3,710
NZ$530 per night
includes taxes & fees
Image gallery for Hot Tub | Close to Downtown | Game Room | Fire Pit
1010 out of 10 rating
Exceptional
(26 reviews)
Hot Tub | Close to Downtown | Game Room | Fire Pit
Lexington, Kentucky
7% off
Price is NZ$9,026
NZ$9,026
NZ$1,289 per night
includes taxes & fees
Image gallery for Luxurious 3 BR Distillery District Townhouse - Eight Belles
1010 out of 10 rating
Exceptional
(10 reviews)
Luxurious 3 BR Distillery District Townhouse - Eight Belles
Lexington, KY
7% off
Price is NZ$6,005
NZ$6,005
NZ$858 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castlewood Park
Treetops Solar Sanctuary
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
1840 Historic Antebellum Estate in the heart of the Bluegrass
Sleeps 20 · 8 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
264 reviews(264 reviews)
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Sleeps 13 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
Horse Show on Sherman
Sleeps 7 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
65 reviews(65 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