Holiday rentals in Bourbon

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Top-rated holiday rentals in Bourbon

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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, 180 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, 245 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, 210 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
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, 476 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
Guest house in Cuba
4.92 out of 5 average rating, 127 reviews

Fox Ridge: Winter sunrises are the best!

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.

Guest favourite
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, 350 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.

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, 137 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
A wooden picnic table is positioned in front of a cabin with a rustic wooden facade. Two red chairs are placed beside the entrance, which features a white door. A gray vehicle is parked nearby on gravel.
Cabin in Bourbon
4.92 out of 5 average rating, 53 reviews

Bourbon Railroad Cabin near Blue Springs Ranch

The Bourbon Railroad cabin is #3 in our Rockwoods Ridge Cabins Series. It is a 2 Queen bedroom and 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. 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 kitchen features wooden cabinetry with a modern finish, complemented by stainless steel appliances including a refrigerator and microwave. A spacious countertop offers ample preparation space, while a glass dining table is surrounded by white chairs, creating a bright and functional atmosphere.
Flat in Saint James
4.92 out of 5 average rating, 236 reviews

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.

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, 188 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 😉

Top guest favourite
A spacious loft area is arranged with a cozy sitting area featuring a tan leather couch, blue armchair, and a circular dining table. A large bed is positioned against the wall, with elegant window treatments framing the natural light. A piece of art depicting a forest scene adds character.
Loft in Washington
5 out of 5 average rating, 422 reviews

2nd Street Loft - Riverview

Complete Rehab, this historic 1883 storefront building hosts a well known artist and his gallery on the 1st floor. Above is your "loft space" close to wineries, Amtrak, featuring great views of the Missouri River. You’ll love this Downtown Washington location because of the walkable shops, bars, and restaurants many in historic buildings. The loft is great for couples, solo adventurers, and business travelers who can walk a flight of stairs.

Top guest favourite
Home in Saint James
4.98 out of 5 average rating, 321 reviews

Cozy Cottage•2BR•On Route 66•Near Wineries

Enjoy a clean, warm, cozy, comfortable stay in this renovated 2-bed, 1-bath home in historic Saint James, ideal for families, friends, and pets. Unwind around the outdoor fire pit or explore nearby shops, Leatherwood Cigar Lounge, and Sybill’s. Just minutes from Maramec Springs, Forest City Bike Trail, Rolla MS&T, and Fort Leonard Wood.

Popular amenities for Bourbon holiday rentals

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