Holiday rentals in Bourbon

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Top-rated holiday rentals in Bourbon

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Top guest favourite
Two kayaks are stored on a rack near a serene pond, surrounded by lush green trees. Two white adirondack chairs face the water, providing a tranquil spot to relax. A small dock extends into the pond, inviting for fishing or kayaking activities.
Cabin in Bland
4.99 out of 5 average rating, 141 reviews

Crooked Creek Cabin. Private Setting on a Pond .

Kick back and relax in this rustic yet modern cabin. Just a little over an hour from St Louis. Enjoy a quite relaxing setting in the woods remodeled in 2021. Family friendly. Enjoy fishing in the private pond, exploring or kayaking. Foosball table. Smart TV, WIFI , Assortment of games and DVDs. White Mull Winery ,Large deck overlooking the pond. . Fire Pit, Nearby Winery, Antiquing. Stores and restaurants. Gasconade River. Hunting Ranch Adorable kids room. FISHING ONLY WHAT YOU CAN EAT

Top guest favourite
Home in Saint James
4.98 out of 5 average rating, 185 reviews

Vineyard Ridge Farmhouse•3BR•Sleeps 8• w/fire pit

Discover a hidden gem near historic Saint James, where comfort and relaxation await. This beautifully renovated 3-bed, 2 bath home is perfect for unwinding with family & friends. Enjoy nearby downtown boutique shopping, Leatherwood Handmade Cigar shop, and fine dining at Sybil’s. Explore the STJ Winery, Pub Brew House, Meramec Springs, & Forest City Mountain Bike Trail. A short drive to Cuba, Steelville, Rolla,MS&T,& Fort Wood, this vacation rental offers ideal balance of relaxation & adventure.

Top guest favourite
A single-story home features a light grey exterior and a gabled roof. Two large windows allow natural light, and a small porch is flanked by flower planters. A well-maintained lawn with scattered shrubs and flowers surrounds the house.
Home in Cuba
4.94 out of 5 average rating, 186 reviews

Cozy Corners

Cozy Corners, built in 1945, offers approximately 900 sq. ft. You, my guests, are recipients of the wall verses that I put on the walls while I was living there, before I knew the house's future occupation. Due to my personal life style and choices, I do not provide TV, but I am now offering WiFi. Pets (pet fee applies) and children are welcome, but no additional supplies are provided at this time. A Ring doorbell monitors both outside doors. Come enjoy my favorite home town known as mural city.

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, 250 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

Top guest favourite
Cabin in Steelville
4.95 out of 5 average rating, 134 reviews

Cabin with Private River Access and Hot Tub

🏡 Country Cabin Relaxed Farm Stay | Hot Tub, Open Space & Country Charm Country Cabin is a laid-back retreat set on a 300-acre century cattle farm in the Meramec River Valley, offering wide-open space, peaceful surroundings, and an authentic Ozark farm experience. Surrounded by pasture and woods, this cabin is perfect for guests who want to slow down, enjoy the outdoors, and experience life on a working farm—while still having easy access to Meramec River adventures through 4J Vacation Rentals

Top guest favourite
Farm stay in Steelville
4.99 out of 5 average rating, 161 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, 489 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.

Superhost
A red cabin with a metal roof is set against a backdrop of green trees. A gravel pathway leads to the cabin entrance, which features a covered porch. Natural landscaping includes large rocks and a distinct wheel decoration set among nearby trees.
Cabin in Bourbon
4.77 out of 5 average rating, 361 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, 152 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 spacious green lawn spreads across the foreground, bordered by trees. A two-story farmhouse, renovated and modernized, stands to the left, while a red barn is visible to the right, creating a harmonious rural scene under a clear blue sky.
Farm stay in Owensville
4.99 out of 5 average rating, 105 reviews

Modern Country Farm House with beautiful views

Relax with the whole family or friends at this peaceful place to stay. Located just 6 miles south of Owensville, Mo this newly renovated farm house will provide you the countryside escape you have been looking for with no shortage of amenities. This 2 story farm house was originally constructed in 1888 as a multi family boarding house before the Kreter family purchased it in the 1930’s. In 2021 we made the decision to completely restore the house and bring it to its modern day glory.

Top guest favourite
Home in Villa Ridge
4.95 out of 5 average rating, 195 reviews

Serenity Valley• Secluded Escape • No Cleaning Fee

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional sofa queen bed for up to 4 guests. Relax on the patio, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

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
4.99 out of 5 average rating, 206 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 😉

Popular amenities for Bourbon holiday rentals

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