Vacation rentals in Bourbon

4.99 out of 5 average rating, 118 reviews

A tranquil gazebo is situated on a gentle slope beside a calm pond, surrounded by a grove of trees. The landscape features a mix of grassy areas and natural rock elements, with reflections of the trees visible on the water's surface.

Cabin in Bland

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

4.94 out of 5 average rating, 158 reviews

The entrance features a gabled roof with shingle siding. The house number '406' is prominently displayed above the entryway. Two hanging planters adorned with purple plants are suspended from the porch beams, adding a touch of greenery to the welcoming facade.

Home in Cuba

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.

4.97 out of 5 average rating, 223 reviews

Farm stay in Saint James

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

4.9 out of 5 average rating, 195 reviews

Home in Sullivan

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.

4.99 out of 5 average rating, 137 reviews

Farm stay in Steelville

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.

The bathroom features a simple layout with a white sink and wooden cabinetry. A wooden toilet seat complements the rustic charm. Soft towels sit neatly on a lace-covered shelf, while a shower curtain partially conceals the bathtub. Warm lighting enhances the welcoming atmosphere.

4.92 out of 5 average rating, 439 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.

4.92 out of 5 average rating, 114 reviews

Guesthouse in Cuba

Fox Ridge: Nature retreat with private trail!

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 circular pool is surrounded by a wooden deck, featuring a smooth entrance with stairs. The clear blue water reflects the surrounding greenery, providing a tranquil setting for relaxation.

4.78 out of 5 average rating, 310 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 $130 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.

5 out of 5 average rating, 52 reviews

10 Private Acres Close to Rivers, Hiking, Caves, P

Summer is here at Cedar Grove Cabin! This private property is on 10 secluded acres close to the Meramec River, hiking trails, caves & wineries! It’s the perfect spot to relax & enjoy nature. Book now and bring your family, friends, pets, or that special someone for a cozy stay surrounded by nature. If under 25 please contact host for full house rules. No parties at this property. Valid photo ID & rental contract to be signed within 48 hours of booking + $500 security deposit hold.

The bathroom features a wall of natural wood planks, bringing an earthy element to the space. A vintage speed limit sign is displayed prominently, complemented by sleek black towel holders and a circular towel ring. The atmosphere merges rustic charm with modern functionality.

4.87 out of 5 average rating, 55 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.

4.92 out of 5 average rating, 214 reviews

An outdoor space is showcased, featuring a seating arrangement with wicker furniture and orange cushions surrounding a fire pit. Paved flooring extends across the area, while a decorative barrier and lamps enhance the setting. A view of greenery and a gravel path is visible in the background.

Apartment in Saint James

James Stay at the Old Opera House

Nestled in the heart of the Ozarks, this completely renovated 1900s property has been restored into a charming AirBNB stay. This property is perfect for business travel, couples, and small families. Guests will enjoy their stay at this two bedroom apartment located in Historic St. James, adjacent to Route 66. This property is within walking distance to local favorites including Rich's Famous Burgers, Historic Johnnie’s Bar, and a short drive to Sybil’s for fine dining.

4.96 out of 5 average rating, 124 reviews

Treehouse in Saint Clair

Lady Asha Yurt/Treehouse!

Hummingbird Hollow Outdoors Lady Asha Yurt/Treehouse. Experience an authentic, rustic and secluded glamping experience on a beautiful Farm Animal Sanctuary with horses, donkeys, sheep, goats and potbellied pigs grazing beneath you, a true animal lover's heaven on earth. There is an comfortably sized and uniquely designed bell tent on an elevated platform nestled in the trees. Cozy futon beds with linens, and multiple cooking options for convenient camping fun.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Bourbon vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Bourbon

4.93 out of 5 average rating, 15 reviews

A modern kitchen and dining area features a large island with three stools, illuminated by pendant lighting. White cabinetry complements the marble countertops. A wooden dining table and a decorative plant enhance the open concept design. Stainless steel appliances are visible in the background.

Home in Owensville

Peaceful Countryside Getaway

JordanRating, 5 stars4 months ago

Beautiful home with comfortable beds & couches. Lots of space to enjoy family and relax. Decorated beautifully with plenty of towels, blankets, cooking utensils etc for you to feel right at home! Layne was also a great host & responded quickly to any & all questions & concerns.

4.94 out of 5 average rating, 81 reviews

A pleasant outdoor space is shown, featuring a wooden deck with seating options under a shaded area. A large tree provides natural cover, while a tranquil pond is visible nearby, surrounded by open grass and a backdrop of greenery.

Cottage in Cherryville

Quiet Cherryville cottage

KennethRating, 5 stars4 weeks ago

We were looking for a place to stay for a night, but this little house gave us so much more. It had a very inviting atmosphere and the host left notes around the house with very helpful information. They met my expectations and then exceeded them. I'm so thankful for them to have us and I would stay there again!

5 out of 5 average rating, 49 reviews

A welcoming porch features a comfortable rocking chair adorned with a decorative pillow. Two lanterns hang beside a window, framed by black shutters. Lush ferns and a textured rug create a cozy atmosphere, with a glimpse of a green landscape visible in the background.

Home in Saint James

Get Cozy in the Country - The Cottage on Luca Hill

StephanieRating, 5 stars1 day ago

Our camping plans got rained out so we had to pivot and find somewhere to stay last minute. This place happened to be available… we booked and we arrived an hour later. This home is clean and situated on a nice property not too far off the highway. We were very pleased with the obvious intention that went into making this home cozy and comfortable . I probably said “I could live here” at least 10 times. The hosts are gracious and kind and I would highly recommend this place as a lovely little getaway spot.

5 out of 5 average rating, 24 reviews

An open cabin interior showcases a kitchenette with modern appliances and a cozy seating area featuring a sofa. A small dining table with four chairs is positioned near the window. Natural light illuminates the space through two windows, enhancing the rustic wooden walls and ceiling.

Cabin in Saint James

Freis' haus Cabin

NancyRating, 5 stars2 weeks ago

An absolutely wonderful and perfect place for us while attending the Folky Fish Festival at Maramec Springs park. The outdoor space is fantastic with fire pit/grill/chairs. Loved sitting on the front porch every morning drinking coffee and listening to the birds. Highly recommend.

4.97 out of 5 average rating, 74 reviews

Home in Saint James

Charming 2 bedroom home - The Winchester.

DavidRating, 5 stars1 week ago

Great home away from home. Everything was as described, very peaceful and quiet neighbourhood. A couple of deer walked around the yard while I was on the back deck. I would definitely stay again if in the area

4.94 out of 5 average rating, 17 reviews

A bright and airy kitchen area is visible, featuring white cabinets and a window that allows natural light to fill the space. A small dining table with two chairs is positioned nearby, and a staircase leads to an upper level, enhancing the open layout.

Cabin in Steelville

Kelly's Cottage at Three Rivers Retreat

ScottRating, 5 stars4 weeks ago

Loved the place and hope to stay again someday down the road! Unique layout. Peaceful spaces, inside and outside. Comfy bed!

5 out of 5 average rating, 67 reviews

A black spider is seen against a yellow fabric surface, creating a stark contrast. The spider's body exhibits a notable red hourglass marking on its abdomen. Fine threads of web can be observed in the surrounding area, indicating its presence.

Home in Cherryville

The Mushroom House in Forest on 80 Acres

AleyshaRating, 5 stars1 week ago

The place was cozy, clean, adorably decorated and private in the woods, just where we wanted to be. The hosts were very responsive, and helpful whenever we needed them. It was a great stay and we will definitely be back again!