Holiday rentals near Castlewood Park
We found 498 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:26 Sept - 3 Oct
Image gallery for Fully Renovated | Finished Basement | Luxury Beds | Games
1010 out of 10 rating
Exceptional
(64 reviews)
Fully Renovated | Finished Basement | Luxury Beds | Games
Lexington, KY
7% off
Price is AU$4,497
AU$4,497
AU$642 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 AU$10,204
AU$10,204
AU$1,458 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$5,256
AU$5,256
AU$751 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom in Lexington
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Cozy 1-bedroom in Lexington
Lexington, KY
7% off
Price is AU$1,406
AU$1,406
AU$201 per night
includes taxes & fees
Image gallery for Entire Home in Hamburg!
1010 out of 10 rating
Exceptional
(22 reviews)
Entire Home in Hamburg!
Lexington, KY
7% off
Price is AU$3,011
AU$3,011
AU$430 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
(32 reviews)
Bourbon n Horses themed 3B/2Ba home in beautiful Chevy Chase neighborhood!
Lexington, KY
8% off
Price is AU$3,726
AU$3,726
AU$532 per night
includes taxes & fees
Image gallery for Hot Tub | Great Location | Patio | Grill | Ping Pong
1010 out of 10 rating
Exceptional
(59 reviews)
Hot Tub | Great Location | Patio | Grill | Ping Pong
Lexington, Kentucky
7% off
Price is AU$6,523
AU$6,523
AU$932 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
(94 reviews)
World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail
Lexington, KY
16% off
Price is AU$4,853
AU$4,853
AU$693 per night
includes taxes & fees
Image gallery for 🏇🏼Equestrian & Bourbon Central🥃 👑The Kingston👑 Near Fasig-Tipton & KYSHP🐴
1010 out of 10 rating
Exceptional
(13 reviews)
🏇🏼Equestrian & Bourbon Central🥃 👑The Kingston👑 Near Fasig-Tipton & KYSHP🐴
Lexington, KY
6% off
Price is AU$2,995
AU$2,995
AU$428 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$3,080
AU$3,080
AU$440 per night
includes taxes & fees
Image gallery for Great Location | Patio | Grill | Tempurpedic Beds
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Great Location | Patio | Grill | Tempurpedic Beds
Lexington, Kentucky
6% off
Price is AU$2,333
AU$2,333
AU$333 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 AU$4,720
AU$4,720
AU$674 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
(8 reviews)
Bluegrass Crossing, close to all the attractions in Central Kentucky
Lexington, KY
18% off
Price is AU$3,643
AU$3,643
AU$520 per night
includes taxes & fees
Image gallery for Red Door Retreat
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Red Door Retreat
Lexington, KY
8% off
Price is AU$2,495
AU$2,495
AU$356 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 AU$4,093
AU$4,093
AU$585 per night
includes taxes & fees
Image gallery for 3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX
9.69.6 out of 10 rating
Exceptional
(14 reviews)
3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX
Lexington, KY
8% off
Price is AU$5,188
AU$5,188
AU$741 per night
includes taxes & fees
Image gallery for Colliver House at Claybank Farm
1010 out of 10 rating
Exceptional
(55 reviews)
Colliver House at Claybank Farm
Lexington, KY
8% off
Price is AU$3,897
AU$3,897
AU$557 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$15,336
AU$15,336
AU$2,191 per night
includes taxes & fees
Image gallery for Renovated Train Station on Thoroughbred Horse Farm
1010 out of 10 rating
Exceptional
(270 reviews)
Renovated Train Station on Thoroughbred Horse Farm
Paris, KY
8% off
Price is AU$2,811
AU$2,811
AU$402 per night
includes taxes & fees
Image gallery for Southern Charm- Spacious Townhome Close to UK
1010 out of 10 rating
Exceptional
(30 reviews)
Southern Charm- Spacious Townhome Close to UK
Lexington, KY
7% off
Price is AU$3,025
AU$3,025
AU$432 per night
includes taxes & fees
Image gallery for Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-
Lexington, KY
7% off
Price is AU$2,160
AU$2,160
AU$309 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$3,594
AU$3,594
AU$513 per night
includes taxes & fees
Image gallery for Great Location / Keeneland / Rupp / Fenced Yard / Games
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Great Location / Keeneland / Rupp / Fenced Yard / Games
Lexington, KY
8% off
Price is AU$3,719
AU$3,719
AU$531 per night
includes taxes & fees
Image gallery for Great Location!!! Plenty of space 3BR/2 Bath Ranch Style home.
1010 out of 10 rating
Exceptional
(23 reviews)
Great Location!!! Plenty of space 3BR/2 Bath Ranch Style home.
Lexington, KY
10% off
Price is AU$2,959
AU$2,959
AU$423 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
9.89.8 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Sleeps 13 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
1800’s Historical Log Cabin near I-75 Interstate
Sleeps 6 · 2 bedrooms · 2+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
36 reviews(36 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)
Nature Escape! Unit Near Attractions in GuestHouse Lexington, Parking, Pool!
Sleeps 4 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
4 reviews(4 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
72 reviews(72 reviews)
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All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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