Holiday houses in Bourbon

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Top-rated holiday rentals in Bourbon

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Top Guest favourite
A bright kitchen features wood countertops and white cabinetry. A large sink is positioned under a window, allowing natural light to illuminate the space. A dining area with a wooden table and chairs is visible in the background, complemented by stylish lighting fixtures.
Farm stay in Saint James
4.97 out of 5 average rating, 246 reviews

Sunset Ridge of St James

This is a cozy cottage modern farm house. It sits at the end of a long private driveway surrounded by 250 acres. Beautiful views with trails & great outdoor space. 3 miles off Interstate 44 on the north side of town. Starlink Satellite for high speed internet! Attractions include multiple wineries- St James Winery & Public Brew house. Sybills restaurant, Spencer Manor Winery, Maramec Spring park & multiple rivers for float trips. Missouri S&T is 25 minutes away in Rolla Mo. Sherbert the cat

Guest favourite
A spacious back deck features a propane grill and a glass-top table surrounded by four chairs. The deck overlooks a backdrop of vibrant fall foliage, creating a natural setting that invites relaxation.
Home in Sullivan
4.89 out of 5 average rating, 211 reviews

Comfy Miramiguoa Home

A great view of the woods awaits you from the countryside kitchen window and off the back deck. The 2 bedroom house has a warm cozy feel and can accommodate 6 people. It adjoins Meramec State Park boundary, which has hiking trails, river access, fishing and floating. Nearby is Meramec Caverns, Onondaga Cave, antiquing, restaurants, breweries, wineries and small zoos. Within 1 hours drive is St. Louis, the Katy trail for bicycling. Enjoy a relaxing comfy stay where deer are frequently seen.

Top Guest favourite
A rustic home built of natural wood is framed by blooming pink trees and lush green grass. The structure features a spacious porch with seating, while large windows allow views into the inviting interior.
Farm stay in Steelville
4.99 out of 5 average rating, 158 reviews

Yeary Farms Milt's Place with Private Beach!

An Ozark Oasis in the middle of a working cattle ranch, this custom designed home offers deluxe comfort. With multiple decks, porches and views out every window, this home is the perfect getaway for romantic retreats, family and friends to relax and make memories, artists and writers to host workshops or retreats, or even the single person to just get away from it all. Good dogs welcome, $35 per dog per week, fee collected separately at time of check in. Look for Yeary Farms site for more info.

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, 478 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
Guesthouse in Cuba
4.92 out of 5 average rating, 128 reviews

Fox Ridge: Ozark Hills Nature Retreat

This quiet, charming, private, multi-room is part of a larger lodge home located in the scenic Ozarks outside of historic Cuba, MO. This one bedroom, one bath, one living room walkout basement is perfect for unplugging and connecting to nature, yourself, your partner, or all 3 while enjoying the abundant wildlife. Sit around the fire pit enjoying star gazing while nestled among the Ozark forest. Located 5 miles from Scott's Ford and 4 miles from Riverside public access on the Meramec River.

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
4.77 out of 5 average rating, 356 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, 142 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.

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, 76 reviews

Spring Break Escape | Log Cabin on 10 Acres | Fire

Ready for a Spring Break that actually feels like a break? 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.

Top Guest favourite
A covered patio area is illuminated by soft twinkle lights, creating a welcoming ambiance for evening gatherings. Comfortable seating and a dining table provide space for relaxation and meals. The surrounding lawns and trees offer a tranquil rural setting.
Cabin in Steelville
4.95 out of 5 average rating, 128 reviews

Cabin with Private River Access and Hot Tub

In the middle of a rolling 300-acre working cattle ranch in the Missouri Ozarks, behind a classic split rail fence, sits Country Cabin— a comfy 3-bedroom home in the mesmerizing Meramec River Valley. Close to some delicious local wineries but far enough away to provide total peace and quiet, your family will cherish the memories they’ll make while relaxing at Country Cabin. And at the end of the day, there’s even a soothing hot tub that will melt all of your remaining stresses away.

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
4.91 out of 5 average rating, 77 reviews

Nostalgic Route 66 Cabin near Blue Springs Ranch

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. You will love the access to Blue Springs Ranch activities, just make reservations with them. We are also near the Meramec River, Blue Springs Creek and Onondaga Cave.

Top Guest favourite
The cozy bedroom features a large bed with a checkered blanket and natural wood walls. A fan provides airflow, while a window allows soft light to enter. A dark wooden dresser stands nearby, contributing to the rustic charm of the space.
Cabin in Saint James
4.98 out of 5 average rating, 193 reviews

Cedar Cabin-Angler’s Catch

Cedar Cabin w/King Bed, Fully Stocked Kitchen, Washer/Dryer, Walk-In Shower, Ramp Access, 2 Decks, Fire Pit, Grill, Free Parking, and 1.3 miles from Beautiful Maramec Spring Park. A trout fisherman’s catch or a couple’s cozy getaway. Close to several Ozark attractions including Maramec Springs Park, Montauk State Park, Current River, Huzzah River, and more. The cabin also has a love seat twin sofa sleeper and is 5 miles from town. Hope to see you soon 😉

Guest favourite
The exterior of a modern loft cabin is shown, featuring a brown metal facade with a green roof. Large windows allow natural light, framed by tall, leafless trees. A small porch is visible at the front, complemented by a stone pathway leading to the entrance.
Loft in Steelville
4.84 out of 5 average rating, 177 reviews

Meramec Scenic View Loft cabin on Meramec River

Secluded but with all the comforts. Beautiful new construction loft cabin ON the Meramec River. Three minute walk to the river. Two upstairs bedrooms each with queen beds. Two full baths. Fully furnished kitchen. Two separate sitting areas, satellite TV and INTERNET available. Two new roll away beds. Covered porch for grilling or just relaxing. Fire pit for marshmallows and star gazing, hiking on private 50 acres.

Popular amenities for Bourbon holiday rentals

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