Holiday rentals near Castlewood Park
We found 509 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:15 Aug - 22 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 AU$14,541
AU$14,541
AU$2,077 per night
includes taxes & fees
Image gallery for Trailside Oasis•Entire house,12 guests, 7mi to KHP
9.89.8 out of 10 rating
Exceptional
(23 reviews)
Trailside Oasis•Entire house,12 guests, 7mi to KHP
Lexington, KY
8% off
Price is AU$5,579
AU$5,579
AU$797 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
(8 reviews)
Heated, Saltwater Pool-Hot Tub-GameRm-Bar-near Keeneland-Bourbon Trail-Dogs OK!
Nicholasville, KY
12% off
Price is AU$13,031
AU$13,031
AU$1,862 per night
includes taxes & fees
Image gallery for Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants
1010 out of 10 rating
Exceptional
(48 reviews)
Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants
Lexington, KY
8% off
Price is AU$6,553
AU$6,553
AU$936 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 AU$3,243
AU$3,243
AU$463 per night
includes taxes & fees
Image gallery for Bluegrass Oasis - Entire house,12 guests, 5mi to KHP
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Bluegrass Oasis - Entire house,12 guests, 5mi to KHP
Lexington, KY
8% off
Price is AU$7,897
AU$7,897
AU$1,128 per night
includes taxes & fees
Image gallery for "The Meridian" Modern Stay near Downtown / Airport
9.89.8 out of 10 rating
Exceptional
(26 reviews)
"The Meridian" Modern Stay near Downtown / Airport
Lexington, KY
8% off
Price is AU$3,919
AU$3,919
AU$560 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 AU$6,768
AU$6,768
AU$967 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
8% off
Price is AU$8,988
AU$8,988
AU$1,284 per night
includes taxes & fees
Image gallery for Napa Hous - 7BD, 7.5 BA, Bar - Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Napa Hous - 7BD, 7.5 BA, Bar - Downtown
Lexington, KY
8% off
Price is AU$12,696
AU$12,696
AU$1,814 per night
includes taxes & fees
Image gallery for Upscale downtown Lexington townhome
1010 out of 10 rating
Exceptional
(52 reviews)
Upscale downtown Lexington townhome
Lexington, KY
8% off
Price is AU$9,275
AU$9,275
AU$1,325 per night
includes taxes & fees
Image gallery for Bluegrass Crossing, close to all the attractions in Central Kentucky
8.88.8 out of 10 rating
Excellent
(6 reviews)
Bluegrass Crossing, close to all the attractions in Central Kentucky
Lexington, KY
11% off
Price is AU$4,037
AU$4,037
AU$577 per night
includes taxes & fees
Image gallery for Modern Cheerful Bluegrass Beauty
1010 out of 10 rating
Exceptional
(18 reviews)
Modern Cheerful Bluegrass Beauty
Lexington, KY
11% off
Price is AU$7,935
AU$7,935
AU$1,134 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 AU$6,462
AU$6,462
AU$923 per night
includes taxes & fees
Image gallery for Urban Luxury: Stylish 3-Bedroom Townhome Near ALL Lexington's Prime Attractions
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Urban Luxury: Stylish 3-Bedroom Townhome Near ALL Lexington's Prime Attractions
Lexington, KY
8% off
Price is AU$8,543
AU$8,543
AU$1,220 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
8% off
Price is AU$3,201
AU$3,201
AU$457 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
(66 reviews)
⭐️Stylish & Cozy Ranch⭐️ Patio, Fenced Back Yard, Fire 🔥Pit-all the essentials!
Lexington, KY
11% off
Price is AU$3,320
AU$3,320
AU$474 per night
includes taxes & fees
Image gallery for Hot Tub | Close to Downtown | Game Room | Fire Pit |
1010 out of 10 rating
Exceptional
(59 reviews)
Hot Tub | Close to Downtown | Game Room | Fire Pit |
Lexington, Kentucky
7% off
Price is AU$6,725
AU$6,725
AU$961 per night
includes taxes & fees
Image gallery for Minutes to Keeneland/Airport/UK & more!
1010 out of 10 rating
Exceptional
(10 reviews)
Minutes to Keeneland/Airport/UK & more!
Lexington, KY
8% off
Price is AU$3,402
AU$3,402
AU$486 per night
includes taxes & fees
Image gallery for Few and Proud
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Few and Proud
Lexington, KY
7% off
Price is AU$3,019
AU$3,019
AU$431 per night
includes taxes & fees
Image gallery for Renovated Train Station on Thoroughbred Horse Farm
1010 out of 10 rating
Exceptional
(268 reviews)
Renovated Train Station on Thoroughbred Horse Farm
Paris, KY
8% off
Price is AU$2,835
AU$2,835
AU$405 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 AU$6,595
AU$6,595
AU$942 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 AU$5,415
AU$5,415
AU$774 per night
includes taxes & fees
Image gallery for Cozy, Comfortable & Convenient
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Cozy, Comfortable & Convenient
Lexington, KY
7% off
Price is AU$3,054
AU$3,054
AU$436 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
73 reviews(73 reviews)
1800’s Historical Log Cabin near I-75 Interstate
Sleeps 6 · 2 bedrooms · 2+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
33 reviews(33 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)
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)
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
68 reviews(68 reviews)
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
265 reviews(265 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