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 NZ$16,594
NZ$16,594
NZ$2,371 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 NZ$6,105
NZ$6,105
NZ$872 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 NZ$14,870
NZ$14,870
NZ$2,124 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 NZ$7,144
NZ$7,144
NZ$1,021 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$3,516
NZ$3,516
NZ$502 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
7% off
Price is NZ$8,807
NZ$8,807
NZ$1,258 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$7,377
NZ$7,377
NZ$1,054 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 NZ$4,308
NZ$4,308
NZ$615 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 NZ$9,751
NZ$9,751
NZ$1,393 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 NZ$14,253
NZ$14,253
NZ$2,036 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 NZ$10,059
NZ$10,059
NZ$1,437 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 NZ$4,425
NZ$4,425
NZ$632 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 NZ$8,848
NZ$8,848
NZ$1,264 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$7,046
NZ$7,046
NZ$1,007 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 NZ$3,677
NZ$3,677
NZ$525 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 NZ$9,278
NZ$9,278
NZ$1,325 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 NZ$3,633
NZ$3,633
NZ$519 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 NZ$7,321
NZ$7,321
NZ$1,046 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 NZ$3,721
NZ$3,721
NZ$532 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 NZ$3,306
NZ$3,306
NZ$472 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 NZ$3,103
NZ$3,103
NZ$443 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$7,192
NZ$7,192
NZ$1,027 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$5,910
NZ$5,910
NZ$844 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 NZ$3,343
NZ$3,343
NZ$478 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