Vacation rentals with outdoor seating in Woodford County

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Top-rated outdoor seating rentals in Woodford County

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

An airy living space is showcased, featuring large windows that invite natural light and provide views of the surrounding fields. Comfortable seating arrangements with a mix of couches and chairs are positioned around a central area rug, highlighting a handcrafted coffee table and a wood stove.

Chalet in Wilmore

4.91 out of 5 average rating, 138 reviews

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

Top guest favorite

A newly built cottage is displayed from an angle, showcasing the covered front porch with wooden railings. Rocking chairs are positioned on the porch, under ceiling fans. Natural surroundings frame the structure, highlighting the inviting outdoor space.

Cottage in Salvisa

4.97 out of 5 average rating, 134 reviews

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

Top guest favorite

An outdoor space is displayed featuring a circular fire pit surrounded by several chairs. A gravel area is present, bordered by trees, with a clear view of the cottage’s blue exterior. Stacked firewood is visible nearby, offering a rustic charm.

Tiny home in Versailles

5 out of 5 average rating, 20 reviews

Bluegrass & Bourbon Cozy Cottage

Welcome to our cozy cottage in Woodford County, right on the Kentucky Bourbon Trail! Just a 10-minute walk to downtown, you'll find coffee shops, restaurants, bakeries, parks, & The Amsden Bourbon Bar. Iconic spots like Woodford Reserve, Castle & Key, & Keeneland are all within 7 miles. Though visible, the quiet cottage is tucked away with a private drive, offering a peaceful retreat. Whether you're into bourbon, horses, hiking, or just relaxing, you’ll feel right at home. Book any tours early!

Guest favorite

A natural landscape is visible, showcasing a serene river bordered by trees. The view extends to the water, reflecting the surrounding foliage. The foreground includes a grassy area with fallen leaves, framed by wooden support beams of the structure.

Home in Kentucky

4.9 out of 5 average rating, 111 reviews

The Stagg House on the Ky River

Nestled on the Kentucky River in Frankfort, KY, our peaceful retreat is surrounded by historic chestnut trees and wildlife like deer & cardinals. Just 5 miles from Buffalo Trace, 6.7 miles from Castle & Key, and 10 miles from Woodford Reserve and Whiskey Thief, it’s ideal for bourbon enthusiasts. Enjoy the river beach, backyard BBQs in summer, or cozy nights by the fireplace in winter—wood provided. Fully stocked kitchen, pet and family-friendly, with a secluded vibe yet close to the main road.

Top guest favorite

A serene pond reflects surrounding trees and a well-maintained private dock that offers access to kayaking and fishing. The tranquil water is complemented by a clear blue sky dotted with soft clouds, creating a peaceful and natural setting.

Cabin in Versailles

5 out of 5 average rating, 22 reviews

River Retreat: Cabin Getaway

Welcome to your ultimate riverfront escape at our charming cedar cabin nestled in the thoroughbred capital of the world. This peaceful two-bedroom retreat comfortably sleeps six & offers a private dock on a serene pond. Enjoy kayaking and fishing right at your doorstep, or unwind by the fire pit under the stars. With easy access to the famous Keenland Racetrack, Shaker Village and the Bourbon Trail, you'll experience the perfect blend of adventure and relaxation surrounded by vibrant wildlife.

Guest favorite

The charming exterior of a cottage is framed by a large tree and green grass. A red metal roof contrasts with the light-colored siding. The front porch features two potted plants at either side of the entrance, while the surrounding landscape shows open fields and a clear blue sky.

Farm stay in Versailles

4.91 out of 5 average rating, 440 reviews

Bluegrass Country Cottage

Enjoy a quaint, private, quiet & charming little place to call your own, on a small, working (seasonal) Thoroughbred horse farm. Green acreage, lovely scenes and sunsets. Located in horse country, between historic Winstar Farm and Lane's End Farm, just a short drive to small town USA, Versailles; historic Midway; and to the nearby City of Lexington, home of the Kentucky Wildcats, Horse Capital of the World, Bourbon Country & so much more. Pets allowed (2 max), well behaved, pet fee applies.

Top guest favorite

Cottage in Lawrenceburg

4.94 out of 5 average rating, 124 reviews

Bourbon Barrel Cottages #2 on the Kentucky Bourbon Trail

LEAVE THE CLEANING TO US! Kick back and relax in this calm, stylish space 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. Perfect retreat for couples traveling together or individuals looking for privacy and quiet. We’re located directly between 4 of the biggest bourbon distilleries on the trail and 20 minutes from anything you’d like to see and do! **There will be a $500 for smoking inside of the cottage

Top guest favorite

The exterior of The Dew Drop In is framed by two large trees, showcasing a well-manicured lawn. The house, painted in light colors, is set back from the foreground, with a wraparound porch visible. A wooden fence outlines the property, enhancing the natural setting.

Farm stay in Midway

5 out of 5 average rating, 102 reviews

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's Bluegrass region, The Dew Drop In, (newly constructed in 2018) is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY's Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.

Top guest favorite

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

4.95 out of 5 average rating, 176 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

Top guest favorite

A wide porch features white wicker chairs and a swing, surrounded by well-maintained greenery. Red geraniums hang in planters, adding a splash of color. The space offers a serene spot for relaxation, accessible to guests of the coach house.

Guesthouse in Wilmore

4.96 out of 5 average rating, 152 reviews

Coach House at the 1898 Red Bud B & B

Lovingly renovated coach house unit was originally the workshop attached to the back of the coach house. It is a ground floor accommodation with private entrance located behind the main bed & breakfast. We are only two city blocks from Asbury! We make a perfect base to explore the area. The Bourbon Trial, numerous horse farm tours, vineyards, Keeneland, the Horse Park, and historic sites such as Shaker Village of Pleasant Hill. Only 11 miles from Lexington.

Top guest favorite

A patio area features a round metal table surrounded by four chairs with colorful cushions. A potted plant sits on the table, while the surrounding wooden deck is complemented by greenery and trees. The scenic view includes a gentle slope and hints of a working farm.

Cabin in Versailles

4.96 out of 5 average rating, 142 reviews

Handcrafted Rustic Cabin on the Bourbon Trail

The cabin has been entirely built by the owner, Doris, (with help from family and friends) from reclaimed and local salvaged materials. Located on a beautiful Kentucky Scenic byway, on a working farm, the cabin is only 15 minutes from Wild Turkey Distillery, the town of Versailles , golf courses, dining, shopping, wineries and other major distilleries. 35 minutes from Keeneland race course, downtown Lexington, UK, Rupp Arena, the Horse Park and more .

Top guest favorite

Home in Frankfort

5 out of 5 average rating, 160 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, fully renovated, open space home in a country neighborhood setting. The home is the perfect retreat for your next getaway to Kentucky. Conveniently situated only a 1/4 mile from Castle and Key Distillery and 2 miles from Woodford Reserve. 1/2 mile from the highly rated restaurant and bourbon bar, The Stave. Indulge in the ultimate bourbon tasting experience, knowing that comfort awaits you at your cozy haven.