A historic building with a prominent tower, surrounded by a well-maintained lawn and American flags.

Holiday Homes in Bourbon

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Bourbon holiday homes

A spacious living area with a leather sofa, a cowhide rug, and a staircase leading to an upper level.

1. Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat

Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat
Bourbon
10.0 out of 10, Exceptional, (4 reviews)
"Very charming lil cabin! It was perfect for a solo trip. I’d love to come back with my husband for a romantic weekend getaway."
United States
Wendy L.
The price is €322
includes taxes & fees
27 Oct - 28 Oct
Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat
A kitchen with a brick wall, wooden ceiling beams, a large island with stools, and a dining table with chairs.

2. Twin Bricks Railhouse near Route 66

Twin Bricks Railhouse near Route 66
Bourbon
10.0 out of 10, Exceptional, (3 reviews)
"Everything was as advertised, great place to stay. I would book again."
United States
Vicki W.
Twin Bricks Railhouse near Route 66
A hot tub with a blue light, surrounded by outdoor furniture and red umbrellas, with a pool and trees in the background.

3. Club Boulders by Pinemark® Heated Pool+Hot Tub

Club Boulders by Pinemark® Heated Pool+Hot Tub
Bourbon
10.0 out of 10, Exceptional, (3 reviews)
"Every detail was thought of at this property, had a great little getaway!"
United States
Jen S.
The price is €722
includes taxes & fees
27 Oct - 28 Oct
Club Boulders by Pinemark® Heated Pool+Hot Tub
A wooden cabin with a balcony, a wooden deck, and a tree with red leaves.

4. Heart of The Meramec River Cabin with SXS trails and River Access, Pets Welcome

Heart of The Meramec River Cabin with SXS trails and River Access, Pets Welcome
Bourbon
The price is €616
includes taxes & fees
27 Oct - 28 Oct
Heart of The Meramec River Cabin with SXS trails and River Access, Pets Welcome
A multi-level room with a staircase, a chandelier, and a bed with pillows.

5. Riverbend Getaway 134-Luxury & Comfort sleep 20+ nearby-swim, float, hike, relax

Riverbend Getaway 134-Luxury & Comfort sleep 20+ nearby-swim, float, hike, relax
Leasburg
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful, spacious, plenty of towels and blankets."
United States
Kayla W.
The price is €664
includes taxes & fees
27 Oct - 28 Oct
Riverbend Getaway 134-Luxury & Comfort sleep 20+ nearby-swim, float, hike, relax
A spacious living room with a ceiling fan, a chandelier, a dining area with a red tablecloth, and a sofa.

6. Riverbend Getaway-Adventure awaits- minutes to swim, float, fish, hike and relax

Riverbend Getaway-Adventure awaits- minutes to swim, float, fish, hike and relax
Leasburg
8.8 out of 10, Excellent, (5 reviews)
"We had a great stay and have recommended to family/friends. This is a beautiful property and a home with lots of character."
United States
Eli B.
The price is €553
includes taxes & fees
8 Nov - 9 Nov
Riverbend Getaway-Adventure awaits- minutes to swim, float, fish, hike and relax
A kitchen with white cabinets, a microwave, a refrigerator, and a wooden dining table.

7. Cozy 2-bedroom house in Cuba, MO.

Cozy 2-bedroom house in Cuba, MO.
Cuba
9.6 out of 10, Exceptional, (8 reviews)
"Nice spot by Route 66"
United States
Ann W.
The price is €138
includes taxes & fees
8 Nov - 9 Nov
Cozy 2-bedroom house in Cuba, MO.
A spacious living area with a sofa, blue armchairs, a coffee table, and a rug.

8. 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
10.0 out of 10, Exceptional, (48 reviews)
"Beautifully appointed and great location for exploring the area!"
United States
Laura P.
The price is €148
includes taxes & fees
8 Nov - 9 Nov
The Concord: A charming 2-bed 2-bath pet friendly house in historic Saint James
A mobile home with a patio area, outdoor seating, and potted plants.

9. #1 Cabin at Red Oak Valley

#1 Cabin at Red Oak Valley
Canaan Township
10.0 out of 10, Exceptional, (2 reviews)
"Fabulous"
United States
Moira M.
#1 Cabin at Red Oak Valley
A house with a gravel driveway, a horse in the background, and a barbecue grill on the porch.

10. Crooked Creek Ranch Farmhouse

Crooked Creek Ranch Farmhouse
Steelville
10.0 out of 10, Exceptional, (54 reviews)
"Great place! Plenty of areas for hiking and outdoor adventures!"
United States
Jean M.
The price is €220
includes taxes & fees
27 Oct - 28 Oct
Crooked Creek Ranch Farmhouse
A modern kitchen with grey cabinets, a central island, and a dining area with brown chairs.

11. Get Cozy in the Country - The Cottage on Luca Hill

Get Cozy in the Country - The Cottage on Luca Hill
Saint James
9.6 out of 10, Exceptional, (37 reviews)
"Good location , clean home, all the items provided that are needed for a short term stay."
United States
K K.
The price is €220
includes taxes & fees
31 Oct - 1 Nov
Get Cozy in the Country - The Cottage on Luca Hill
A living room with a sofa, armchair, coffee table, and a rug.

12. Pet-friendly 2BR with fenced yard

Pet-friendly 2BR with fenced yard
Saint James
9.8 out of 10, Exceptional, (29 reviews)
"Cozy house for the family and pets to stay in. St. James was a fun stay with the small town vibes. Happy with the stay and would stay again."
United States
Richie M.
The price is €237
includes taxes & fees
1 Nov - 2 Nov
Pet-friendly 2BR with fenced yard
A modern kitchen with dark cabinetry, a stainless steel sink, a microwave, and a stove.

13. Spacious 3BR near downtown St. James

Spacious 3BR near downtown St. James
Saint James
9.6 out of 10, Exceptional, (35 reviews)
"Lots of space in a convenient location."
United States
Billy A.
The price is €248
includes taxes & fees
27 Oct - 28 Oct
Spacious 3BR near downtown St. James
A spacious living room with a ceiling fan, a herringbone-patterned floor, and a large window with sheer curtains.

14. Vineyard Ridge Farmhouse • 3BR • 2BA • Vineyard View • Fire pit •

Vineyard Ridge Farmhouse • 3BR • 2BA • Vineyard View • Fire pit •
Saint James
10.0 out of 10, Exceptional, (48 reviews)
"We enjoyed a great stay!"
United States
Heather A.
Vineyard Ridge Farmhouse • 3BR • 2BA • Vineyard View • Fire pit •
A kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

15. Large home, Pet friendly

Large home, Pet friendly
Union
9.8 out of 10, Exceptional, (41 reviews)
"The rental was beautiful, clean and well taken care of. It was decorated for the 4th of July and was so fun and welcoming. The backyard was a huge bonus, especially when traveling with dogs or kids! Kitchen was very large."
United States
Anonymous traveller
The price is €364
includes taxes & fees
27 Oct - 28 Oct
Large home, Pet friendly
A wooden deck with a table and chairs, overlooking a body of water and trees.

16. Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake

Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake
Saint Clair
Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake
A room with a wooden wall panel, a flat-screen TV mounted above a wooden console, a white lantern, and a remote control on the console.

17. Delightful 3-bedroom house with AC in charming Davisville many close attractions

Delightful 3-bedroom house with AC in charming Davisville many close attractions
Davisville
8.8 out of 10, Excellent, (3 reviews)
"Very clean, great rural view, plenty of towels and things for a group. Fun stay."
United States
Karigan C.
The price is €225
includes taxes & fees
1 Nov - 2 Nov
Delightful 3-bedroom house with AC in charming Davisville many close attractions
A patio with outdoor seating overlooking a lake, surrounded by trees and greenery.

18. Mid Century Modern Home w/ Private Pool & Lake on 50 Acres

Mid Century Modern Home w/ Private Pool & Lake on 50 Acres
Union
9.8 out of 10, Exceptional, (108 reviews)
"Fantastic property and exceptional host."
United States
Matt B.
The price is €1,426
includes taxes & fees
8 Nov - 9 Nov
Mid Century Modern Home w/ Private Pool & Lake on 50 Acres
A spacious living area with a sectional sofa, a ceiling fan, and a view into the kitchen and dining area.

19. Spacious Franklin County Retreat on 80 Acres!

Spacious Franklin County Retreat on 80 Acres!
Luebbering
9.8 out of 10, Exceptional, (9 reviews)
"It was a lovely stay, too short."
United States
Reece
Spacious Franklin County Retreat on 80 Acres!
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.
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Top Bourbon Hotel Reviews

Pinemark Inn & Suites

Pinemark Inn & Suites

10/10 Excellent
"Very clean and good breakfast...I'd stay here again."
Michael 1-night trip
Posted 3 days ago
Pinemark Inn & Suites

Find out more about Bourbon

Bourbon Holiday Homes information

Number of reviews
435
Accommodation
77 Holiday Homes
Lowest Price
€138
Highest Price
€1,426