House vacation rentals in Woodford County

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Top-rated house rentals in Woodford County

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Guest favorite

Home in Lawrenceburg

4.98 out of 5 average rating, 42 reviews

#4 Bourbon Barrel Cottages Ky Trail Distilleries

LEAVE THE CLEANING TO US! Kick back and relax in this calm, stylish cottage in the center of Kentucky’s Bourbon Country. Enjoy wildlife and nature in one of our 5 two bedroom cottages. Each sits on two acres. We’re located directly between 4 of the biggest bourbon distilleries on the trail and 20 min from anything! Sit out on your deck or at your own private fire pit at night and listen to the sounds of birds, frogs and other wildlife. **There will be a $500 for smoking inside of the cottage**

Nov 21 – 28

G$49,076 GYD per night

Superhost

Home in Midway

5.0 out of 5 average rating, 3 reviews

Midway Meadows on the Park

NEW LISTING. Great for Keeneland. Short walk to the eclectic downtown Midway and all its restaurants and specialty shops or walk out the back door and take your very own walking path to the Walter Bradley Park (see photos for Park and park map) which lead to several walking trails meandering along Lees Branch Creek. Relax on the large screened-in porch in the evening or make a fire in the great room. You will be pleasantly surprised when you step into this 1880’s restored railroad homestead.

Jul 9 – 16

G$47,003 GYD per night

Guest favorite

Home in Versailles

5.0 out of 5 average rating, 22 reviews

Birdsong Valley on Bourbon Trail

Great central location on Bourbon Trail. Close to Lexington, airport, Keeneland, Ride the Rails, Horse Park, Shakertown, many other attractions. You will love our 3 bedroom charming home on 2.2 beautiful acres in peaceful community. Perfect for couples, friends, families, singles to explore distilleries, horse farms, quaint small towns of Versailles, Midway, Lawrenceburg, country backroads, much more. OR relax, enjoy nature, butterflies, birds, deer. Let us make lodging highlight of your visit.

Feb 15 – 22

G$29,302 GYD per night

Guest favorite

Home in Midway

5.0 out of 5 average rating, 56 reviews

Midway Cottage-Vineyard, Bourbon Trail, Horses

Enjoy the great outdoors at Saddlestone Cottage, an old family farm house fully renovated offering all new amenities. It's in heart of horse country, but close to everything...Ky Bourbon Trail, Ky Horse Park, Keeneland, Equus Run Vineyards, Old Friends, and historic Midway. Excellent dining choices are close by in Midway, Lexington, Georgetown and Frankfort. You have the perfect front porch view of picturesque Equus Run Vineyards, located just across the road, and access to South Elkhorn Creek.

Oct 25 – Nov 1

G$65,875 GYD per night

Guest favorite

Home in Midway

4.99 out of 5 average rating, 98 reviews

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!

Aug 27 – Sep 3

G$29,148 GYD per night

Guest favorite

Home in Midway

4.99 out of 5 average rating, 68 reviews

The Bees Wing

Built in 1889 this 2800 sq ft home has lots of charm and plenty of space to accommodate up to 8 guests. With two king beds, a queen, two twins, a pull out sofa bed, plus three full baths, dining room, living room, completely remodeled kitchen, plus a spacious screened in porch overlooking the 16 x 40 in ground salt water pool and fabulous backyard, what more could you ask for in the heart of horse country? The heart of Midway with its renowned restaurants and galleries is just a block away!

Nov 29 – Dec 6

G$90,792 GYD per night

Guest favorite

Home in Lexington

5.0 out of 5 average rating, 25 reviews

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

Jan 4 – 11

G$43,227 GYD per night

Guest favorite

Home in Versailles

4.97 out of 5 average rating, 33 reviews

Riverside Roost -bourbon themed water front home

Welcome to Riverside Roost! "The Roost" is nestled in a little community on the serene Kentucky River in Woodford County, although still close to Frankfort and Lexington. Yes, you are on the Bourbon Trail! While at The Roost, enjoy cooking on the grill, playing board games with the family, lounging on the deck or spending a day on the river. There are also plenty of distilleries and restaurants nearby. Whatever you do as the sun passes over and the river passes by, make memories together.

Jan 7 – 14

G$49,980 GYD per night

Guest favorite

Home in Wilmore

5.0 out of 5 average rating, 29 reviews

*KY Charm*Asbury/Lex-King bed-foosball-piano-games

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

Mar 1 – 8

G$27,169 GYD per night

Guest favorite

Home in Harrodsburg

4.93 out of 5 average rating, 205 reviews

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

Apr 13 – 20

G$21,666 GYD per night

Guest favorite

Home in Versailles

4.93 out of 5 average rating, 122 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Aug 12 – 19

G$27,578 GYD per night

Guest favorite

Home in Midway

5.0 out of 5 average rating, 64 reviews

Midway Cottage, Keeneland, Distilleries, Pool

Minutes from Keeneland racetrack and in the heart of the Bourbon Trail our 1901 cottage has a fenced backyard, patio, grill, private pool open seasonally April to October (unheated) kitchen, laundry, dining room, living room, tv in lr, tv in bedroom and WIFI. A short walk to Main Street restaurants and shops. Minutes from Keeneland Race Track, the Kentucky Horse Park and our world famous Bourbon distilleries, it is surrounded by the most beautiful horse farms in the Bluegrass.

Jun 25 – Jul 2

G$70,327 GYD per night