Book Holiday Homes in Bourbon

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Featured Holiday Homes in Bourbon

The Concord: A charming 2-bed 2-bath pet friendly house in historic Saint James

The Concord: A charming 2-bed 2-bath pet friendly house in historic Saint James

Saint James MO
The price is NZ$369 per night from 5 Jan to 6 Jan
NZ$369
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this holiday home in St. James. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Rosati Winery Museum and ...
Opens in a new windowThe Concord: A charming 2-bed 2-bath pet friendly house in historic Saint James
The James Stay on Historic Route 66, minutes away from Wineries & Restaurants

The James Stay on Historic Route 66, minutes away from Wineries & Restaurants

Saint James MO
The price is NZ$293 per night from 25 Dec to 26 Dec
NZ$293
25 Dec - 26 Dec
includes taxes & fees
Stay at this holiday home in St. James. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions St. James Winery and Meramec Vineyards ...
Opens in a new windowThe James Stay on Historic Route 66, minutes away from Wineries & Restaurants
A nice view of the woods awaits you from the countryside kitchen window and deck

A nice view of the woods awaits you from the countryside kitchen window and deck

Sullivan MO
Stay at this holiday home in Sullivan. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Meramec Caverns and Meramec State Park are located ...
Opens in a new windowA nice view of the woods awaits you from the countryside kitchen window and deck
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Townside Blue House

Townside Blue House

Saint James MO
The price is NZ$304 per night from 25 Dec to 26 Dec
NZ$304
25 Dec - 26 Dec
includes taxes & fees
Stay at this holiday home in St. James. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions St. James Winery and Meramec Vineyards ...
Opens in a new windowTownside Blue House
Luxury Home in Woods w/ Easy Access to Large Private Gravel Bar on Meramec River

Luxury Home in Woods w/ Easy Access to Large Private Gravel Bar on Meramec River

Steelville MO
Stay at this holiday home in Steelville. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowLuxury Home in Woods w/ Easy Access to Large Private Gravel Bar on Meramec River
Vineyard Ridge Farmhouse

Vineyard Ridge Farmhouse

Saint James MO
The price is NZ$357 per night from 29 Dec to 30 Dec
NZ$357
29 Dec - 30 Dec
includes taxes & fees
Stay at this holiday home in St. James. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Rosati Winery Museum and Meramec Vineyards ...
Opens in a new windowVineyard Ridge Farmhouse
 Charming house near Maramec Spring Park, Steelville/St. James

Charming house near Maramec Spring Park, Steelville/St. James

Steelville MO
Stay at this holiday home in Steelville. Enjoy a garden, laundry facilities and patios. Popular attractions Woodson K. Woods Memorial Conservation Area and Maramec ...
Opens in a new window Charming house near Maramec Spring Park, Steelville/St. James
2BR | Pet-Friendly | Fenced Yard | Near Wineries

2BR | Pet-Friendly | Fenced Yard | Near Wineries

Saint James MO
The price is NZ$403 per night from 31 Dec to 1 Jan
NZ$403
31 Dec - 1 Jan 2026
includes taxes & fees
Stay at this holiday home in St. James. Enjoy a garden, laundry facilities and patios. Popular attractions St. James Winery and Meramec Vineyards are located ...
Opens in a new window2BR | Pet-Friendly | Fenced Yard | Near Wineries
Located In The Foothills Of The Ozarks, Enjoy A Peaceful Setting At The Lodge.

Located In The Foothills Of The Ozarks, Enjoy A Peaceful Setting At The Lodge.

Cherryville MO
Stay at this holiday home in Cherryville. Enjoy a garden, laundry facilities and an in-room coffee maker.
Opens in a new windowLocated In The Foothills Of The Ozarks, Enjoy A Peaceful Setting At The Lodge.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Bourbon Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Bourbon vacation homes are the perfect way for you to wing it.

Holiday houses in Bourbon let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Bourbon in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Bourbon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Bourbon with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Bourbon vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Bourbon Holiday Homes essential information

Accommodation
64 Holiday Homes
Lowest Price
NZ$236
Highest Price
NZ$600
Popular accommodation
The Concord: A charming 2-bed 2-bath pet friendly house in historic Saint James , The James Stay on Historic Route 66, minutes away from Wineries & Restaurants, A nice view of the woods awaits you from the countryside kitchen window and deck, Townside Blue House , Luxury Home in Woods w/ Easy Access to Large Private Gravel Bar on Meramec River, Vineyard Ridge Farmhouse , Charming house near Maramec Spring Park, Steelville/St. James, 2BR | Pet-Friendly | Fenced Yard | Near Wineries, Located In The Foothills Of The Ozarks, Enjoy A Peaceful Setting At The Lodge.

Top trending hotels in Bourbon

Escape to PARADISE on 10 sprawling acres in which to do anything you please!

Escape to PARADISE on 10 sprawling acres in which to do anything you please!

Leasburg MO
The price is NZ$600 per night from 4 Jan to 5 Jan
NZ$600
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly cabin in Bourbon. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
Opens in a new windowEscape to PARADISE on 10 sprawling acres in which to do anything you please!
Country Cabin with Jacuzzi Tub Near Blue Springs Ranch

Country Cabin with Jacuzzi Tub Near Blue Springs Ranch

Bourbon MO
The price is NZ$284 per night from 28 Dec to 29 Dec
NZ$284
28 Dec - 29 Dec
includes taxes & fees
Stay at this family-friendly cabin in Bourbon. Enjoy a garden, patios and in-room jetted baths. Popular attractions Onondaga Cave and Onondaga Cave State Park ...
Opens in a new windowCountry Cabin with Jacuzzi Tub Near Blue Springs Ranch
RGM Farms Guesthouse, rustic yet comfy with kitchenette.

RGM Farms Guesthouse, rustic yet comfy with kitchenette.

Bourbon MO
The price is NZ$236 per night from 29 Dec to 30 Dec
NZ$236
29 Dec - 30 Dec
includes taxes & fees
Stay at this cabin in Bourbon. Enjoy a garden, an in-room coffee maker and housekeeping.
Opens in a new windowRGM Farms Guesthouse, rustic yet comfy with kitchenette.
Save an average of 15% on thousands of hotels when you're signed in
Real Log Cabin with Seasonal Pool and Hot Tub near Blue Springs Ranch

Real Log Cabin with Seasonal Pool and Hot Tub near Blue Springs Ranch

Bourbon MO
Stay at this family-friendly cabin in Bourbon. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Onondaga Cave and Onondaga Cave State ...
Opens in a new windowReal Log Cabin with Seasonal Pool and Hot Tub near Blue Springs Ranch
Don't see what you're looking for?
See all available properties in Bourbon
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.