House vacation rentals in Woodford County

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Top-rated house rentals in Woodford County

Guests agree: these houses are highly rated for location, cleanliness, and more.

Guest favorite
Home in Midway
Country Cottage in Horse and Bourbon Country
This completely updated cottage is located on a scenic byway voted one of the ten best scenic drives in the United States, on which you will see thoroughbred farms for which Kentucky is famous. Keeneland and the Kentucky Horse Park are within 20 minutes. There are 4 distilleries within 10 miles, 11 within 30 miles, and 23 within an hour’s drive. Two bedrooms, new kitchen, new bathroom, washer and dryer, covered porch, deck, air conditioning, wifi, cable TV, and ample parking. Relax and enjoy!
Mar 30 – Apr 6
$132 per night
4.99 out of 5 average rating, 93 reviews
Guest favorite
Home in Lexington
CINDERELLA'S GUEST HOUSE
New Enchanting two story cedar and glass couple's retreat featuring an eclectic mix of mid-century modern, industrial and artist influences. The home has one bedroom, one bath, and a laundry/office with a rooftop deck. Living room and a fully equipped kitchen are on the first floor with a ground level outdoor deck. Bedroom and laundry/office both open onto the rooftop deck through sliding patio doors where you find yourself at eye level with a grove of black walnut trees, like a treehouse
Aug 22 – 29
$180 per night
5.0 out of 5 average rating, 23 reviews
Guest favorite
Home in Wilmore
*KY Charmer*Asbury/Lex-fireplace-King bed-foosball
This spacious, newly renovated private basement is the perfect lodging for visiting families, commuting students, or out-of-town explorers. Located in a peaceful subdivision in the quaint town of Wilmore, we're within walking distance to Asbury University and Seminary, Centennial Park, hiking trails, and a bustling main street with shops, cafes, and craft ice cream. We are an easy 20-30 minute drive from Lexington, Keeneland, Rupp Arena, and the Bluegrass Airport. Jess Co Permit #9248
May 7 – 14
$112 per night
5.0 out of 5 average rating, 24 reviews

Popular amenities for Woodford County house rentals

House rentals with a pool

Guest favorite
Home in Lawrenceburg
Restful Bourbon Trail Lodge with Pool and Hot Tub
May 21 – 28
$370 per night
4.82 out of 5 average rating, 144 reviews
Guest favorite
Home in Lexington
Midcentury/Industrial gas Fireplace & Fine Bedding
May 10 – 15
$139 per night
4.94 out of 5 average rating, 130 reviews
Guest favorite
Home in Midway
The Bees Wing
Oct 27 – Nov 3
$376 per night
4.99 out of 5 average rating, 67 reviews
Guest favorite
Home in Midway
Midway Cottage, Keeneland, Distilleries, Pool
Jul 6 – 13
$295 per night
5.0 out of 5 average rating, 61 reviews
Superhost
Home in Lexington
Private for 4 No cleaning fee Discounts up to 20%
Sep 11 – 18
$80 per night
4.81 out of 5 average rating, 21 reviews
Guest favorite
Home in Georgetown
Modern Farmhouse/20 acres/9 miles from Horse Park
Jan 21 – 28
$450 per night
4.97 out of 5 average rating, 74 reviews
Guest favorite
Home in Lexington
4 BR 3 Bath 9 beds! Hot Tub, Pool, Movie room!
May 10 – 17
$443 per night
4.87 out of 5 average rating, 76 reviews
Guest favorite
Home in Lexington
Close to Everything! Beautiful two-story home
Mar 19 – 26
$316 per night
4.98 out of 5 average rating, 53 reviews
Guest favorite
Home in Lexington
Lex Fun Zone! Amenities! Hottub! Pool! Arcade!
Oct 28 – Nov 4
$359 per night
5.0 out of 5 average rating, 61 reviews
Superhost
Home in Lexington
Southland Swim House
Jul 12 – 19
$279 per night
4.86 out of 5 average rating, 49 reviews
Guest favorite
Home in Lexington
The Lexington Ranch House
Aug 18 – 25
$118 per night
4.94 out of 5 average rating, 32 reviews
Guest favorite
Home in Lexington
4 Bed Home w/ Pool in the heart of Horse Country
Mar 10 – 17
$495 per night
5.0 out of 5 average rating, 11 reviews

Weekly house rentals

Guest favorite
Home in Lawrenceburg
#4 Bourbon Barrel Cottages Ky Trail Distilleries
Dec 8 – 15
$235 per night
4.97 out of 5 average rating, 38 reviews
Guest favorite
Home in Kentucky
The Stagg House on the Ky River
Nov 6 – 13
$172 per night
4.95 out of 5 average rating, 21 reviews
Guest favorite
Home in Frankfort
The Field House by Castle & Key
Jan 6 – 13
$972 per night
4.95 out of 5 average rating, 19 reviews
Superhost
Home in Versailles
Bourbon Trail*Sauna*Keeneland
Oct 11 – 18
$274 per night
4.75 out of 5 average rating, 4 reviews
Guest favorite
Home in Versailles
Riverside Roost -bourbon themed water front home
Sep 2 – 9
$188 per night
4.96 out of 5 average rating, 27 reviews
Guest favorite
Home in Midway
Midway Cottage-Vineyard, Bourbon Trail, Horses
Dec 22 – 29
$268 per night
5.0 out of 5 average rating, 53 reviews
Guest favorite
Home in Wilmore
Heavenly Home in the Heart of Horse Country
Jul 1 – 8
$249 per night
4.92 out of 5 average rating, 38 reviews
Guest favorite
Home in Versailles
Pin Oak Gables
Aug 10 – 17
$199 per night
4.95 out of 5 average rating, 37 reviews
Superhost
Home in Lexington
Silver Streak Retreat
May 21 – 28
$150 per night
4.64 out of 5 average rating, 28 reviews
Superhost
Home in Harrodsburg
The River Side Lodge- with private boat dock!
Jun 22 – 29
$150 per night
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Versailles
The gathering place for friends and family
Jan 23 – 30
$226 per night
4.81 out of 5 average rating, 59 reviews
Guest favorite
Home in Versailles
Birdsong Valley on Bourbon Trail
Dec 31 – Jan 7
$122 per night
5.0 out of 5 average rating, 12 reviews

Private house rentals

Home in Versailles
Jockey Suite at Sugar Hill Farm
Jan 17 – 24
$176 per night
4.61 out of 5 average rating, 28 reviews
Home in Midway
Midnight Train to Midway
Aug 15 – 22
$114 per night
4.7 out of 5 average rating, 10 reviews
Home in Midway
Cottage in horse country!
Sep 19 – 26
$338 per night
5.0 out of 5 average rating, 4 reviews
Home in Versailles
Family-Friendly Versailles House: 12 Mi to UK!
Dec 2 – 9
$251 per night
5.0 out of 5 average rating, 4 reviews
Home in Versailles
Bluegrass Cottage
Dec 27 – Jan 3
$270 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Midway
Merefield Farm Cottage
Sep 28 – Oct 5
$180 per night
4.71 out of 5 average rating, 48 reviews
Home in Midway
Trackside 3-Bedroom Home
Mar 19 – 26
$225 per night
4.5 out of 5 average rating, 8 reviews
Home in Midway
Midway Retreat
Dec 27 – Jan 3
$799 per night
4.93 out of 5 average rating, 14 reviews
Guest favorite
Home in Lexington
Malcomb Farm
Mar 2 – 9
$600 per night
4.93 out of 5 average rating, 15 reviews
Home in Harrodsburg
Rare KY River home with private boat ramp
Jan 20 – 27
$227 per night
4.79 out of 5 average rating, 29 reviews
Guest favorite
Home in Midway
The Cottage
Feb 1 – 8
$225 per night
4.96 out of 5 average rating, 74 reviews
Guest favorite
Home in Frankfort
The Bourbon Trail & Horse Country EpiCenter
Aug 27 – Sep 3
$165 per night
4.8 out of 5 average rating, 15 reviews

Destinations to explore