Vacation rentals in Howardstown

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Top-rated vacation rentals in Howardstown

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Top guest favorite

A well-kept, single-story home is set against a backdrop of a clear blue sky and colorful autumn foliage. The house features a welcoming front porch and is surrounded by expansive grassy areas, with a small lake visible nearby.

Home in New Haven

Mom's House

Welcome to this lovely well-kept home in the country with a small lake and a large yard! Relax on the deck, sit by the lake, watch the sun rise over the hill in a place that feels like home. Near the Bourbon Trail! 5 mins to KY Railway Museum. 10 mins to Log Still Distillery & The Amp, and Lincoln's Boyhood home. 20 mins to Bardstown, Hodgenville, 25 mins to E'Town. 40 miles to Churchill Downs. The house is well stocked with everything you may need including breakfast items! Plenty of parking.

5.0 out of 5 average rating, 41 reviews

Top guest favorite

A rustic kitchen area features a wooden countertop with bar stools and metallic paneling. Various appliances, including a microwave and stove, are visible. The space is adorned with vintage signs, adding a touch of character to the design.

Barn in Campbellsville

Peaceful Getaway in the Country

Enjoy this rustic, yet cozy, two-story barnhouse located near bourbon country. Perfect for a couple's getaway, it has open lofts with a comfy king-sized bed, a kitchen stocked with all the essentials, laundry room, wood burning stove & two bathrooms: one with a walk-in shower & one with a soaker tub. This listing's interior is ready, however the exterior is still a work in progress as we continue to create comfortable outdoor spaces. Must see all pictures to appreciate what this place offers.

4.97 out of 5 average rating, 205 reviews

Top guest favorite

A spacious living area features comfortable seating with light-colored sofas, a wooden coffee table, and a patterned area rug. Large windows allow natural light to fill the space, offering views of the outdoor greenery. Exposed beams add architectural interest to the ceiling.

Farm stay in Hodgenville

Spacious country living, game room, fire pit

This newly renovated & spacious home is located within minutes from town. Located on a quiet farm with views of wooded land and a large pond. Inside there is a full working kitchen, spacious dining room and a game room equipped with shuffle board, air hockey, card table, arcade machine and board games! Something for everyone! Just mins from town 20min drive to Elizabethtown Sports Park 30mins to Bardstown -the bourbon capital Our small town has some great mom and pop restaurants & shopping

5.0 out of 5 average rating, 42 reviews

Top guest favorite

Home in Elizabethtown

Elizabethtown Sports Park/Bourbon Trail

Escape to our spacious retreat just minutes from Elizabethtown Sports Park and 20 minutes from world-class Bourbon Trail distilleries. Nestled in the woods, it offers privacy and room for the whole family. After games or tastings, relax in the hot tub, gather around the firepit, and soak in the peaceful setting. The perfect base for tournaments, bourbon adventures, or simply unwinding in the Bluegrass. Whether it's competition or relaxation that brings you here this home has it all!

5.0 out of 5 average rating, 59 reviews

Top guest favorite

A serene view is captured of a wooden bridge extending over a calm body of water, with a cabin visible in the background. Surrounding trees reflect in the water, enhancing the natural beauty of the space. A second pavilion is seen to the right.

Cabin in Lebanon

*NEW* Secluded Cabin On Private Lake

Woodland Acres is located in the Heart of Kentucky, with spectacular views all around, year-round! Come enjoy this piece of heaven right on the Bourbon Trail! This unique and spacious hideaway has breathtaking views and is situated just 7 minutes from downtown Lebanon, KY. Enjoy a private lake and fishing dock, take a hike through the vegetation that surrounds you, or enjoy a cup of coffee on the wraparound porch. Ideal for leisure seekers, nature lovers, and families alike!

5.0 out of 5 average rating, 70 reviews

Guest favorite

A charming cottage features a light yellow exterior with dark shutters, nestled between two large trees. The picturesque yard is well-maintained, with grass surrounding the base of the house, providing a serene and inviting appeal.

Home in New Haven

Fairview Country Cottage

Relax and enjoy a peaceful garden view with sounds of nature all around. A clean newly renovated house and guests have the whole place to themselves. Conveniently located less than 2 miles from Log Still Distillery and The Amp. Only 20 minutes from Historic Bardstown, 2 miles from the Abbey of Gethsemani and a short drive to Maker's Mark Distillery! We are excited to welcome you into our cottage! You will retain your privacy and check in with your own personal door code.

4.93 out of 5 average rating, 67 reviews

Top guest favorite

Home in Hodgenville

King Bed | Walk Downtown | Coffee Bar | Cozy Home

Located near downtown Hodgenville, this newly renovated home is perfect for travelers, tournament families, wedding guests, or a relaxing stay 5 min near Lincoln’s Birthplace. 🛏️ King bed + queen bed 🚗 10 miles to I-65 ⚾ 18 min to Elizabethtown Sports park 📍 Walk to food, coffee & shops 💒 Near local wedding venues 🏞️ 50 min to Mammoth Cave 🍳 Stocked kitchen + oils & spices ☕️ Coffee bar 🔐 Keyless entry 💻 Fast WiFi 🖤 Blackout shades 🌙 Late check-ins welcome

5.0 out of 5 average rating, 43 reviews

Top guest favorite

An aerial view captures the property surrounded by lush farmland. The layout includes a swimming pool and neighboring structures, featuring manicured lawns and ample greenery. A winding driveway leads through the landscape, emphasizing the spaciousness of the 72-acre setting.

Farm stay in Raywick

Missy’s unique stays on the bourbon trail .

Welcome to this funky and eccentric property that sits on 72 acres of luscious farmland in the heart of Kentucky, situated along the bourbon trail .. Previously “Missy’s café ) now turned it into a country getaway for family, Friends or sweethearts .. it is set up for intimate events (extra) or just a nice quiet stay .. it has a beautiful view of the farm and surrounding knobs.. not to far away from civilization, but far enough too get away and enjoy nature

4.97 out of 5 average rating, 149 reviews

Top guest favorite

Home in Loretto

Bourbon Belle Farmhouse - 5 Mins From Makers Mark!

Welcome to our family farmhouse, nestled right on the famous Bourbon Trail! This home has been in our family for three generations and offers a warm, authentic Kentucky experience. Relax on the front porch with a glass of bourbon as the sun sets over rolling hills, or wake up to the gentle sounds of farm life. We’re located directly beside the Barrel Head Airbnb. Feel free to reach out if you’re interested in booking both homes to accommodate more guests!

5.0 out of 5 average rating, 13 reviews

Top guest favorite

A spacious green yard is visible, bordered by trees. A circular driveway leads to a single-story house with a covered front porch. Surrounding grass is neatly mowed, offering ample space for outdoor activities.

Home in Elizabethtown

Secluded country getaway

Bring the whole family to this great place with lots of room for fun.There is a large yard for the kids to play. It has an upstairs exercise room over the garage.A large back porch for grilling or relaxing.There is a wood fire pit plus a gas one too. Plenty of room inside.Easily sleeps 10. It is located close to the interstate and E-town Sports park. A large yard for outside activities. It is quiet and peaceful located on 6 .5 acres.

4.95 out of 5 average rating, 102 reviews

Top guest favorite

A modern kitchen features sleek white cabinetry and granite countertops. Stainless steel appliances, including a microwave and refrigerator, are visible. A dining table with four black chairs is situated nearby, complemented by natural light streaming in from a window.

Home in Hodgenville

Duplex in Hodgenville

Property located in Hodgenville Ky, just few minutes drive from Abraham Lincoln National Park. 20 min drive to the Elizabethtown Sports Park or the Ford Blue Oval Plant. Hodgenville is also located less than 30 miles from Bardstown, the home of Kentucky Bourbon. The duplex is less than a 10min drive to Mathers Mill, the Barn at hidden Meadows and 15 or less to Christians Landing making this the perfect stay for wedding guest!

4.94 out of 5 average rating, 47 reviews

Top guest favorite

Dome in Raywick

The Dome At The Ridge-Bourbon Trail Glamping

Escape to the treetops and experience the perfect mix of comfort and adventure in our private geodesic dome. Nestled on the edge of the Kentucky hills, this glamping retreat offers sweeping views of rolling farmland and endless skies. Please note this is a true outdoor experience, and you may encounter wildlife and insects. Perfect for a bourbon trail adventure, a couple’s getaway, or simply unplugging and recharging.

4.98 out of 5 average rating, 62 reviews