Vacation rentals in Bourbon

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Top-rated vacation rentals in Bourbon

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

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Top guest favourite
The bungalow is illuminated by string lights, casting a warm glow around the covered wrap-around porch. The structure's red exterior stands in contrast against the deep blue evening sky, creating a cozy evening ambiance. The surrounding landscape features grass and trees.
Farm stay in Saint James
4.99 out of 5 average rating, 163 reviews

Sunset Valley of St. James- 2 bedroom 1 bath home

This cozy farm cottage sits in the heart of a beautiful farm, yet only 2 miles away from award winning wineries, restaurants, brew house and parks. Newly installed Starlink Satellite for hi-spied wi-fi and internet! Very private and beautifully styled. Minutes from award winning restaurants and wineries. St. James Winery, Sybills Rest, Spencer manor winery. Close to Maramec Spring Park & many rivers for floating. 20 minutes from Missouri S&T & close to Ft Wood. Perfect getaway! 2 queen beds.

Top guest favourite
A unique outdoor structure with an arched wooden door is surrounded by lush greenery. The landscape features manicured grass and stone walls, with decorative plants hanging near the entrance. Lawn games are set up nearby, providing recreational options in a tranquil natural setting.
Tiny homes in Steelville
4.95 out of 5 average rating, 98 reviews

The Hobbit Hideaway

Have you ever wanted to live the simple laid back life of a Hobbit? Well,here is your chance. You will walk through the round wooden doors into the partial underground home,feeling more like a Hobbit with each passing moment. This beautiful tiny home is very private,sitting in the woods,while still having convenient access off Rte.8. Wether it's relaxing watching the deer,rabbits and squirrels play or rafting one of the nearby rivers with a local outfitter you will find this a great getaway.

Top guest favourite
The cabin's exterior features warm wooden logs with a green roof, complemented by a covered porch. A charcoal grill is situated on the porch, with steps leading down to a grassy area. Surrounding landscapes include open fields and distant trees.
Cabin in Bourbon
4.93 out of 5 average rating, 496 reviews

Log Cabin at Meramec Farm

A warm, pine honeymoon cabin surrounded by pastoral Ozark countryside. The Meramec River flows through this seventh generation family farm. Cozy interior includes a kitchenette, dining area, and double bed on main level. All your cooking intensils are provided with coffee, tea, and paper products. DVDs and books available await you up the spiral staircase in the loft. Full bed on main level and two singles bed upstairs. Expansive view from your front porch of the highest bluffs on the Meramec.

Top guest favourite
A cabin exterior is framed by tall trees, featuring a welcoming porch with two red Adirondack chairs. A picnic table is visible nearby, and the ground is covered with gravel, creating a rustic setting. The cabin is built with warm wooden siding.
Cabin in Bourbon
4.92 out of 5 average rating, 87 reviews

Nostalgic Route 66 Cabin with River Access

Nostalgic Route 66 decorated 2-Queen bedrooms, 1 bath Cabin near Blue Springs Ranch on a private drive in a gated community. Right in the middle of Tall Oak Trees with a beautiful sunset from the porch. Unique 3 zoned heating and cooling controlled from each room. This is Cabin #2 of Rockwoods Ridge Cabins. Meramec River access for Rockwoods Ridge Cabins guests only by the New Heart of the Meramec River Cabin. We are also connected to Blue Springs Ranch, Blue Springs Creek and Onondaga Cave.

Top guest favourite
A light-filled living area features a beige sectional sofa with decorative black and white pillows. An ottoman is placed in front of the sofa, complementing the neutral tones. A ceiling fan hangs above, and barn doors lead to another room, offering an open and airy feel.
Cottage in Bourbon
5 out of 5 average rating, 67 reviews

The Cottage “N” near Blue Springs

Enjoy coming home to this beautifully remodeled cottage after a long day on the River. Located just 4.9 miles from the scenic Meramec River, you will love the 4 partially wooded acres & your own private walking trail with plenty of room for yard games & and a camp fire. No matter the season, relax & enjoy a cup of coffee in the enclosed front porch with an electric fireplace. Don’t miss the view of the lake on the adjacent property & enjoy wildlife when sitting on the screened-in back porch!

Superhost
A rustic cabin features red exterior walls and a metal roof, situated on a well-manicured lawn. The entrance is framed by bushes, with a covered porch and a small seating area visible on one side. Lush trees provide a natural backdrop.
Cabin in Bourbon
4.76 out of 5 average rating, 365 reviews

Cabin In The Woods 2

2 bedroom cabin with queen size beds, full kitchen & bathroom, private hot tub & shared pool (pool is shared between 3 cabins). Price of $135 per night is based on up to 2 people; additional people ages 8 & older $25 extra per person per night. *Hot tub & Pool:we reserve the right to close the hot tub or pool for any mechanical issues that may occur and that is beyond our control. Any type of parties must be pre-approved. We now offer 5 mile float trips! **float trip is additional cost.

Top guest favourite
A modern cabin exterior is shown, featuring warm outdoor lighting and a combination of wood and metal materials. A spacious deck is accessible via steps, while a covered area with a grill and outdoor movie projector is visible on the side. Lush greenery surrounds the property.
Cabin in Leasburg
4.99 out of 5 average rating, 161 reviews

Luxury Cabin Sleeps 6 w/ Hot Tub and Outdoor Movie

Welcome to our Beautiful Luxury Cabin in the Woods—more than just a place to stay, it's an unforgettable experience. Nestled on 9 private acres, this custom-built, Scandinavian-inspired retreat offers the perfect blend of comfort and adventure. While the property features just one other guest cabin nearby, there are NO SHARED AMENITIES, ensuring you have complete privacy during your stay. The cabin is near Onondaga State Cave Park, Meramec River, Float Trips, Wineries and local dining.

Guest favourite
Home in Leasburg
5 out of 5 average rating, 5 reviews

Private Home & Pond - Near River Access & Floating

Welcome to Sunshine Hideout Rental, your private escape on 14 scenic acres in the country. This cozy 2-bedroom (Queen), 1-bath retreat features a game room with a Twin Futon and a covered deck overlooking a peaceful, private, fishing pond. Cook each meal in the fully stocked kitchen. Enjoy nature, explore the land, or relax by the water. Just a few miles from river access and popular floating spots, it’s the perfect mix of quiet getaway and outdoor adventure.

Top guest favourite
A rustic log cabin is shown, featuring a spacious porch with a wooden deck. Outdoor seating includes three metal chairs and a small table, shaded by an umbrella. Surrounding greenery includes shrubs and small plants, enhancing the cabin's natural setting.
Cabin in Bourbon
5 out of 5 average rating, 88 reviews

Log Cabin on 10 Acres | Fire Pit & Pets Welcome

Ready for a private getaway? Relax on 10 peaceful acres where you can unplug, spread out, and reset. As the woods come back to life, you’ll have front-row seats to quiet mornings, fresh country air, and space to truly relax. You'll love the gas fireplace inside, & the outdoor firepit is perfect for s’mores and memory-making under the stars. Valid photo ID & rental contract to be signed within 48 hours of booking + $500 security deposit hold. No parties.

Superhost
Cabin in Steelville
5 out of 5 average rating, 3 reviews

Crooked Creek Cabin

Come visit our unique and tranquil getaway. Nestled on the bank of Crooked Creek, this cabin is a gem, cozy and comfortable. Sit on the front porch sipping coffee or your favorite beverage and listen to the water rush by. Take time to relax by the water and bbq, build a campfire or watch for wildlife. Plenty to see and do with just a short 10/20 minute drive. Floating, wineries, music and more. Don’t miss out on this opportunity!

Guest favourite
A spacious hot tub is illuminated by soft blue lighting, surrounded by a wooden gazebo. Two wine glasses are placed on the edge, inviting relaxation. A grill is visible in the background, and strands of light fill the area, creating a serene evening ambiance.
Cabin in Owensville
4.94 out of 5 average rating, 107 reviews

Guest Cabin at R & J Ranch

Enjoy a relaxing getaway at R & J Ranch! Pour yourself a glass of wine as you soak in the spacious six person hot tub. Gaze at the stars while roasting marshmallows around the campfire. Share laughs during a few rounds of shuffleboard or pool. Whatever you choose to do, this cozy rustic cabin offers a unique combination of relaxation and fun!

Top guest favourite
A modern, single-story cabin with a metal roof is set on a grassy expanse. A covered porch with rocking chairs is visible, providing an inviting outdoor space. Large windows offer views into the cabin, and a chimney rises from the roof.
Cabin in Leslie
4.99 out of 5 average rating, 82 reviews

Lake Cabin Near the Bourbeuse!

Kick back and relax in this newly built, stylish cabin. Enjoy the awesome porch and the great outdoors. Enjoy the lake or take a nice walk to the river. Wineries, restaurants and antique shops are nearby. Great weekend getaway or place for business travelers after a long day. Bring your fishing pole and binoculars!

Popular amenities for Bourbon vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Crawford County
  5. Bourbon