Vacation Rentals By Owner In Springfield, KY

Welcome to The Bourbon Lodge! brbrThis entire 15 acre property will be home during your visit to The Bluegrass region. We have a well maintained walking path through the property which is definitely unique and a firepit. You will love every view from the full wrap around porch and the interior will instantly help you relax. The property is located just 12 minutes off The Bluegrass Parkway between Bardstown and Springfield, KY. Shopping and dining is minutes away and you are within 30 minutes - 1 hour from most distilleries. 2 bedrooms with King beds and attached bathrooms, as well as, a large loft area boasting 2 Queen beds and multiple sitting areas, gives you plenty of room to spread out. The main level has an open floor plan with including kitchen, dining area and spacious sitting area. The walk out basement has another sitting area, bar area, ping pong table and individual dry sauna. But, as mentioned above, the real show stopper is the wrap around porch and beautiful views as far as you can see. $50 pet fee per pet.

Lodge

The Bourbon Lodge - Log cabin, Bourbon Trail, Nature and more!

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(18)

$216.24

Unwind in a 3-bed, 2 bath scenic retreat just 20 min from historic Bardstown and the legendary Bourbon Trail. Complete with a game room featuring a ping-pong and foosball table.brbrTake in rolling-hill sunsets with a nice glass of bourbon from the front porch or back deck, fire up the BBQ grill for dinner or stream movies one of four smart TVs with the Wi-Fi.brbrRural enough to feel secluded but you will be just a short drive to either Bardstown, Springfield or Bloomfield. All of these small towns offer unique dining and tourist experiences. In the heart of bourbon country, there are 20 distilleries within a 45 minute drive of the house. brbrFull kitchen & washer/dryerbrCentral A/C & heatingbrBackyard with wide-open viewsbrBook your countryside getaway today!

Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(7)

$304.9

The Stagg Haus of Springfield is the perfect bourbon trail destination on a picturesque hillside in the heart of the bluegrass. Less than 20 miles from 9+ distilleries, conveniently located off of the scenic bluegrass parkway, and one mile from Abraham Lincoln's homestead. Enjoy the outdoor patio with a blackstone grill, a fully equipped chef's kitchen, and expertly designed and thoughtfully staged interiors with all the comforts of home. This is the Kentucky experience of your dreams.

The Stagg Haus of Springfield- On the Bourbon Trail + Kentucky Countryside

Springfield, Kentucky, United States

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Sleeps

$155.24

Riverside Cabin on the Bourbon TrailbrbrEscape to our unique cabin on the banks of the Beechfork River in Central Kentucky, right on the Bourbon Trail. Perfect for nature lovers and bourbon enthusiasts alike, this cozy retreat is near Maker's Mark, Jim Beam, Barton, and Bardstown Bourbon distilleries.brbrLocation:brEnjoy the best of both worlds with nature at your doorstep and famous distilleries just a short drive away.brbrThe Space:brOur cabin features a minimalist European design, blending modern comfort with natural beauty. It includes a cozy living area, a kitchenette, two bedrooms with a queen-sized beds, and a modern bathroom. Large windows offer stunning river and forest views.brbrAmenities:br- Heating and air conditioningbr- Kitchenette with essential appliancesbr- Fresh towels and linensbr- Complimentary toiletriesbr- Outdoor seating with a fire pitbr- Coffee maker with coffee brbrGuest Access:brYou’ll have full access to the cabin and surrounding grounds. Enjoy peaceful walks along the river and hiking in the nearby foothills.brbrActivities:br- Distillery tours and tastingsbr- Hiking in the foothillsbr- Fishing and kayaking on the riverbr- Stargazing and enjoying nature's soundsbrbrNearby Attractions:br- Maker's Mark Distillery (15 minutes)br- Jim Beam Distillery (20 minutes)br- Bardstown Bourbon Company (25 minutes)br- Barton 1792 Distillery (30 minutes)br- Historic downtown Bardstown (30 minutes)brbrUnplug, unwind, and enjoy a drink (we recommend bourbon) while gazing at the stars and listening to nature. Please note that cell phone service within the unit may be limited, depending on your carrier.

Unique Cabin on the Beechfork River, nestled in the heart of the Bourbon Trail

Springfield, Kentucky, United States

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Select Dates for Price

Located in Springfield KY, enjoy what this 5-bedroom house has to offer. With four queen beds and one king bed, guests find plenty of space to relax comfortably. The house features four bathrooms, two equipped with a refreshing Tub/shower combo and the other two with a full shower, all equipped with the basic complimentary essentials. Stay comfortable year-round with heating and air conditioning throughout. This home features three fully equipped kitchens/living area combos and two in house laundry areas with an iron available to keep your wardrobe looking sharp. There is a swing on the front porch as well as rocking chairs, along with a table/chairs on the side front porch and additional seating on the back deck. Cozy up to the fire pit, as there is also seating, outdoor lighting and a gas/charcoal grill out back. You will have three entrances for ease of access to which bedroom you stay in. Ample parking in the back driveway or street/handicapped parking in front. The front entrance is wheelchair accessible. when you don't feel like grilling out or cooking in one of the beautiful kitchens you will be in walking distance (2-3 minutes) to the Big Bull Steakhouse, Snappy Tomato pizza, or Springfield Nutrition. Two convenient stores (gas stations) and of course your small-town shopping are all in walking distance as well. We are only a 15-minute drive to Lebanon and 20 minutes to Bardstown for even more dining options. This charming and vibrant house invites guests to unwind and make lasting memories. Book now and enjoy everything this house has to offer.

Beautiful, Spacious & Newly renovated home in the heart of downtown Springfield.

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(10)

$162.73

Keep it simple at this peaceful and centrally-located home. Enjoy watching the cattle graze and the farm views while being only minutes from town and in the heart of the Bourbon Trail. Ample space for guests and a dedicated workspace make this the perfect spot for anyone.brbrI will do my very best to accommodate early check-in or late check-out when my schedule allows. There is also plenty of parking available for extra vehicles or if you have a trailer, etc.brbrThe spacebrThis home boasts 3 bedrooms with 2 queen beds and 1 full size bed. Rooms are spacious enough to add air mattresses too. A dedicated office space with free wi-fi and a smart TV are also available. We provide all linens, laundry supplies and a well stocked kitchen. We want you to feel right at home!brbrGuest accessbrThe entire home is available to you and check in is easy through the smart lock.

Townview Farmhouse - Bourbon Trail - Farm Stay

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(16)

$279.27

Sleeps 8 in 3 private bedrooms and one loft space, Master Bedroom has King Bed and en suite large master bath, 2 queen bedrooms and a queen bed in large loft space up a set of spiral stairs in the living area. Huge kitchen with a large island for dining. Cozy living room with huge TV and gas fireplace. Outside is a country dream. Sit on the porches and listen to the birds chirp and watch the whitetail deer. brCentral to the Bourbon Trail, you can hit any of the well known distilleries in less than an hour in any direction. Located out i n the country,but just a quick 10-15 minute drive into Springfield where you can grab a bite to eat at Mordecai's on Main, grab groceries or a delicious plate lunch at Parkview IGA, or shop in one of the little boutiques or antique shops on main street. One hour from both Lexington and Louisville. 20 minute drive to Makers Mark Distillery. 30 minutes to Bardstown.

Country Cottage on the Bourbon Trail, near Bardstown, Peaceful, Family, Couples

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(19)

$173.97

Lawson’s Landing – A Family Farm Retreat with Stunning Views on the Bourbon TrailbrWelcome to Lawsons Landing, a peaceful countryside escape rich in history and full of charm. Nestled in the heart of Springfield Kentucky, our home offers a truly unique farm-stay experience, surrounded by rolling fields, working farmland, and breathtaking views of the rolling hills of Central Kentucky.brbrAbout the Space:brLovingly maintained and updated for modern comfort, this home still carries the charm of its original builders. Wake up to the sights and sounds of farm life, with open pastures, scenic sunrises, and fresh country air right outside your door.br• 3 Bedrooms | 2 Bathrooms | Sleeps 6br• Cozy living room with large windows overlooking the fieldsbr• Fully equipped kitchen for home-cooked mealsbr• Private patio with seating for enjoying your morning coffeebr• Fast Wi-Fi & smart TV for modern conveniencebr• Outdoor gazebo with smart TVbrbrThe Experience:brGuests are welcome to absorb the farm scenery and simply relax in the tranquility of the countryside. Depending on the season, you may see farming activities in action, from planting to harvest along with cattle and sheep grazing the hillside. This is a fully operational farm with the daily hustle and bustle of farm life, including harvest in the fall, planting in the spring, and hay and cattle operations running year-round through the summer and winter. Be sure to wave to Lances Dad when you see him on the farm!brbrLocation & Nearby Attractions:br• 5 min to Lebanon Ky.br• 20 min to Bardstown Ky.br• 30 min to Danville Ky.brCome experience the beauty, history, and hospitality of Lawsons Landing—a place built with love, rooted in history, and dedicated to making new memories. We can’t wait to host you!

Lawsons Landing-On the Bourbon Trail

Springfield, Kentucky, United States

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$281.11

Welcome to your Bourbon Trail basecamp in Springfield, Kentucky — centrally located near Maker’s Mark, Heaven Hill, Jim Beam, Buffalo Trace, and Bardstown’s historic downtown. This dog-friendly 3-bedroom retreat features a private hot tub, firepit, electric fireplace, and fast WiFi — the perfect place to unwind after a full day of distillery tours and tastings.

Explore Bourbon Trail, Hot Tub

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(5)

$353.68

Historic family farm in the heart of bourbon country. Walk in the woods, play in the creek, see a working farm in action. Step back in time . Established in 1792.brbrThe spacebrJust a few miles from Maker’s Mark, Heaven Hill, Willett, and other distilleries.brHike 300 acres. Imagine life on a farm 200 years ago.brbrGuest accessbr300 acres of land to explore.brbrOther things to notebrThe correct address for your GPS isbr8082 Bardstown RdbrSpringfield KY 40069

Country House

Historic Parker’s Landing

Springfield, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(10)

$149.0

Bring the whole family and make lasting memories at this modern and one-of-a-kind retreat! Brand new and thoughtfully designed, our space is packed with fun features to entertain guests of all ages. Nestled on the east side of our charming metal barn, you’ll enjoy complete privacy with dedicated parking and your own cozy front and back porches—perfect for sipping your morning coffee or relaxing after a day of adventure.brbrLocated just minutes from the famous Bourbon Trail, our home is a perfect blend of modern comfort and rustic charm. Highlights include:br• Spiral Staircase to the Barn Loft – A fun and unique feature the kids (and kids at heart) will love.br• Bucket Trolley System – Add a playful touch to your stay by transporting goodies in style.br• Game Wall – Keep the whole family entertained with a variety of games for all ages.br• Gas Fireplace – Snuggle up and enjoy cozy evenings by the fire.br• Pull-Out Couch – Perfect for extra guests or movie nights.brbrWhether you’re here for the Bourbon Trail, exploring the countryside, or just looking for a relaxing escape, we’ve got everything you need to unwind and have fun. Book your stay today and let us help make your visit unforgettable!

Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!

Springfield, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(1)

$388.37

Centrally located in downtown Springfield, this historic home has been revamped to provide you with all the entertainment that you need! 3900 sq. ft so you can bet that you’ll have plenty of space as a group! Makers Mark sits just 15 minutes away and the bourbon capital of the world, Bardstown, only 20! Want to explore more Wild Turkey and 4 Roses sit only 30 minutes away and a day trip to Louisville or Lexington is only an hour! Don’t let the party stop after a day out on the bourbon trail!brThe spacebrIf you are looking to have fun this is your spot! Located in downtown Springfield we are walking distance to local shops and restaurants! Tons of space in our house with a little bit of everything for your group to do! The amenities are top of the line! Just a great spot to come back to after hitting the bourbon trail!brbr***ALWAYS will accommodate early check in or late check out if possible! Ask for availability!brGuest accessbrThe whole house is yours! NOT A DUPLEX!brOther things to notebrIf you have special requests that you may need before booking PLEASE inquire! I know your money is valuable and I want to ensure your stay is best it can possibly be!

Locally Owned Historic Pope House: BRBNTrail FunZone! 3900sqft! Hottub! Fishing!

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(10)

$605.42

Dive into the fun at this two-story country-side home. My goal is to keep you entertained while also having a relaxing vibe for your getaway. Nestled just off the Bourbon Trail, Makers Mark and historic Bardstown are just a short drive. Proximity to Louisville and Lexington are great too! Jump into the pool during the Spring, Summer or Fall season! Our home sits on 3 acres so you will have plenty of yard space! Featuring a very open and spacious Master bedroom and then an additional 3 bedrooms in the basement! WiFi/Cable, Pool Table, Ping Pong Table, Golden Tee Arcade Machine, and all amenities. Friends or family, this will make for a fun trip all around!brbrThe space:brbr-ALWAYS will accommodate early check in or late check out if possible! Ask for availability!br-Can Sleep 10 people comfortablybr-3 Acre Lotbr-Fully fenced in pool (6-foot privacy fence)br-Location is great for your bourbon trail and horse racingbr-Private Parkingbr-Game Area Downstairsbr-Hot Tub Areabr-All new furniturebr-55in TVs up and downstairsbr- Gas Grillbr- Fire Pit (Gas and Wood)brbrGuest accessbrYou have access to the whole house and surrounding grounds!brbrOther things to notebrbrIf you have special requests that you may need before booking PLEASE inquire! I know your money is valuable and I want to ensure your stay is best it can possibly be!

Bourbon Trail POOL Zone! HotTub! PoolTable! PingPong! GoldenTee! BigYard! PETS!

Springfield, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(44)

$673.38

A stunning historic countryside property located in Springfield, KY. A perfect place for a weekend away, bourbon trail homebase, company retreat or large event. The house features three bedrooms, three and a half baths and a full kitchen. The Carriage House features 3 bedrooms, two baths and a game room. With the rental of the house you also have the ability to add on the rental of the private lake located on the property. For event rental details please contact owner. brbrAdditional people may be added to the rental. Please contact us to add on the Carriage House as a part of your stay. This increases the number of people in house to 12 total (6 additional spots). brbrHistory: brBuilt in 1842 the historic Simmstown Manor has lots to offer. The house was originally built by Harvey McElroy for his daughter, Mariah McElroy Simpson. The original owners were devastated by the Civil War and the property was then sold to John Simms. John Simms had amassed a great amount of wealth prior to the war and unlike many others was able to sustain it during the war and use it to purchase the sizable brick mansion and the surrounding lands. After a few years he owned the 2400 acres surrounding the great house. The Simms family completed a two story wing on the north side of the house and moved in in 1868. The house held many grand parties and entertainments during the Simms’ time and often opened its doors to the most prosperous and socially prominent families around. When John Simms wife, Sarah Celclia Simms, died in 1895 he surveyed his 2400 acres of land and divided it among each of his five surviving children. His youngest child, Mary Simms Smith was given Simmstown as her part of the property divide and her father continued to live with her until his death. Upon Mr. Simms' death Mary kept the house and it was passed through the family until 1983 when Mr. and Mrs. E. O. Kelly Jr., the great grandson of Mr. Simms decided to sell the house to the current owner, Mr. Larry Hodge. The house and grounds both went through an extensive renovation with efforts to keep historical aspects in as many ways possible.brbrNote: The home has security cameras to monitor the driveway, as a safety precaution. (This is required to be disclosed to renters.)

Historic Simmstown Manor Located on Bourbon Trail

Springfield, Kentucky, United States

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Bath

Sleeps

Exceptional(9)

$135.94

The Cornerstone Cabin is situated on the historic 1794 built Litsey estate. The lane leading to the property is lined with lush landscape and old stone fence. Cornerstone Cabin is located along the drive and is near the estate house and other historic outbuildings. The property is a mixture of iconic Kentucky countryside, forest and wildlife. The cabin has a covered porch overlooking the property. Inside is a living room, kitchen, bathroom and bedroom. The space is cozy and inviting with plenty of options for comfort and relaxation. Amenities include queen size bed, sofa, shower, refrigerator, oven, microwave, coffee maker, TV, DVD player, board games, ac/heating unit, ceiling fans, table, two cots, extra bedding. *Friendly dog on property and family living in estate house.

Peaceful retreat on the historic 1794 Litsey estate near Springfield, Kentucky.

Springfield, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(144)

$143.98

Our place is close to the Bourbon Trail. You’ll love our cabin because of the warm interior and amazing outdoor space. Our place is good for couples, solo adventurers, business travelers, and families. This cabin located in the country on our 500 acre farm, but you are 3 miles from restaurants, groceries, pharmacies and shops. The location is also central to the distilleries: 15mi to Maker's Mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington, and Louisville.brbrThe cabin is a studio or loft style, so its very cozy for couples. There is not a private bedroom. Families can have fun all together playing games or cards. The downstairs entertainment area is the perfect place to catch a game or favorite TV show. There is Direct TV with a huge package. A DVD/Blu-Ray player is upstairs. There is free Wi-Fi as well. You are going to love it! brbrThe outdoor space includes one of the bathrooms (kept heated in winter). You will have full run of the creek bottom. Feel free to walk about the property and play in the creek. All the privacy you will ever want.

Cozy Cabin center of Bourbon Trail, Near Bardstown, beautiful country views

Springfield, Kentucky, United States

Bath

Sleeps

Exceptional(37)

$459.3

Leave your worries behind when you visit the Hillview House. Spacious and well appointed. Newly remodeled and designed for a family or couples getaway. Nestled right in the middle of the Bourbon Trail, we are an hour or less drive to nearly every distillery in the state! You will love the private rural setting with beautiful views all around you.

Hillview House on the Bourbon Trail

Springfield, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(100)

$567.42

Come to the Bourbon Trail in the Heart of Kentucky! Stay at our beautiful lodge with large common areas perfect for hanging out! Our space is great for family trips, work retreats, or a couples get away! The lodge is located just 3 miles from from restaurants, groceries, pharmacies and shops. But at the Lodge you will enjoy the peace of the country. We are central to all the bourbon distilleries: 15mi to Maker's mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington and Louisville.brbrThe lodge is the top floor of a converted old tobacco barn. Much of the year it serves as a hunting lodge hosting deer and turkey hunters. We use it as a rental during hunting off season. Every bathroom and bedroom is private. You must climb stairs to access the majority of the place. There is a DVD player and DirecTV with a complete package. There is free Wi-Fi as well. We do use the barn to store farm equipment, so we may be in and out of the barn if we are working but will not be in the living quarters. We will try our very best not to bother you! brbrWe do also have a passenger bus that will accommodate those staying with us. We can get you set up to take on your bourbon trail adventure. brbrWe live just down the hill at the house. So if you need us we can help you out, but promise not to bother you otherwise.

Lodge

Lofty Lodge on the Bourbon Trail

Springfield, Kentucky, United States

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Bath

Sleeps

$343.09

Get ready to relax in this 4-bedroom house in Springfid. This marvelous property boasts 1 king bed, 3 queen beds, and 1 twin bed, perfect for a group getaway. With 3 bathrooms, including a jetted bathtub, guests can unwind in style. brbrThe pleasant atmosphere and cool amenities like our full wrap around deck, Screened in porch, Ping Pong Table, 2 living rooms, 3 TVs (2 Roku connected, 1 VHS/DVD combo) full kitchen, washer & dryer, AC, and heating ensure a comfortable stay. We hope you enjoy this taste of peace and serenity in the country, not 5 minutes from Springfield.brbrEnjoy the beautiful views of nature on our wrap around deck, and screened in porch! Comfortably sleeping 9, & up to 12 including couches.brbrNear Springfield (4 miles), Lebanon & Bloomfield (10 miles.), Bardstown (15 miles), and Lexington & Louisville (1 hour). brbrGreat for family trips, retreats! Central to the bourbon trail, including Maker's mark, Jim Beam, Woodford Reserve, and 10-15 mins. away from Springhill Winery. The property utilizes an outdoor security camera system, with no inside cameras, to provide safety and security for our guests. Cameras are positioned on the driveway, front door, covered porch door, master bedroom exterior entrance, and basement door. There are no cameras inside the house. To provide our guests privacy.

Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Springfield, Kentucky, United States

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Bath

Sleeps

Most popular vacation rentals in Springfield

$173.97

Lawsons Landing-On the Bourbon Trail

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$673.38

Historic Simmstown Manor Located on Bourbon Trail

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$605.42

Bourbon Trail POOL Zone! HotTub! PoolTable! PingPong! GoldenTee! BigYard! PETS!

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$567.42

Lodge

Lofty Lodge on the Bourbon Trail

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$459.30

Hillview House on the Bourbon Trail

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$388.37

Locally Owned Historic Pope House: BRBNTrail FunZone! 3900sqft! Hottub! Fishing!

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$353.68

Country House

Historic Parker’s Landing

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$343.09

Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$288.87

Explore Bourbon Trail - Hot Tub - Dog Friendly

Springfield, Kentucky, United States

Bed

Bath

Sleeps

$279.27