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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 €316
includes taxes & fees
13 Sept - 14 Sept
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.
The price is €308
includes taxes & fees
20 Sept - 21 Sept
Twin Bricks Railhouse near Route 66
An aerial view of a property with two main buildings, a paved driveway, and surrounding greenery.

3. Meramec Hideaway Riverside private vacation home

Meramec Hideaway Riverside private vacation home
Bourbon
9.8 out of 10, Exceptional, (7 reviews)
"We had a good experience with our family."
United States
Robert D.
The price is €474
includes taxes & fees
13 Sept - 14 Sept
Meramec Hideaway Riverside private vacation home
A modern living room with a pool view, large windows, and a dining area.

4. 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.
Club Boulders by Pinemark® Heated Pool+Hot Tub
A kitchen with white cabinets, a microwave, a refrigerator, and a wooden dining table.

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

Cozy 2-bedroom house in Cuba, MO.
Cuba
9.8 out of 10, Exceptional, (7 reviews)
"Nice spot by Route 66"
United States
Ann W.
The price is €142
includes taxes & fees
22 Sept - 23 Sept
Cozy 2-bedroom house in Cuba, MO.
A cabin interior with a green door, wooden walls, a window, a wooden bench, and a trash can.

6. Sunset Ridge perfect vacation home near Meramec River

Sunset Ridge perfect vacation home near Meramec River
Leasburg
9.2 out of 10, Wonderful, (7 reviews)
"Will stay again"
United States
Joan J.
Sunset Ridge perfect vacation home near Meramec River
A cabin interior with a green door, wooden walls, a window, a wooden bench, and a trash can.

7. Sportsman's Meadow vacation home near Meramec River

Sportsman's Meadow vacation home near Meramec River
Leasburg
8.8 out of 10, Excellent, (6 reviews)
"A great place to stay for a family reunion!"
United States
Sarah T.
The price is €351
includes taxes & fees
13 Sept - 14 Sept
Sportsman's Meadow vacation home near Meramec River
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, (38 reviews)
"Beautifully appointed and great location for exploring the area!"
United States
Laura P.
The price is €126
includes taxes & fees
11 Sept - 12 Sept
The Concord: A charming 2-bed 2-bath pet friendly house in historic Saint James
A lakeside property with a large house, a smaller red barn, and a well-maintained lawn.

9. Leasburg Lakehouse vacation home & private stocked lake near Meramec River.

Leasburg Lakehouse vacation home & private stocked lake near Meramec River.
Leasburg
9.2 out of 10, Wonderful, (15 reviews)
"Great place to stay. Clean, quiet, good activities for all ages on site. Would definitely return for another stay. "
United States
Sandra M.
The price is €564
includes taxes & fees
12 Sept - 13 Sept
Leasburg Lakehouse vacation home & private stocked lake near Meramec River.
A mobile home with a patio area, outdoor seating, and potted plants.

10. #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.
The price is €188
includes taxes & fees
14 Sept - 15 Sept
#1 Cabin at Red Oak Valley
A house with a gravel driveway, a horse in the background, and a barbecue grill on the porch.

11. Crooked Creek Ranch Farmhouse

Crooked Creek Ranch Farmhouse
Steelville
10.0 out of 10, Exceptional, (52 reviews)
"Great place! Plenty of areas for hiking and outdoor adventures!"
United States
Jean M.
The price is €208
includes taxes & fees
23 Sept - 24 Sept
Crooked Creek Ranch Farmhouse
A multi-level room with a staircase, a chandelier, and a bed with pillows.

12. 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 €582
includes taxes & fees
11 Sept - 12 Sept
Riverbend Getaway 134-Luxury & Comfort sleep 20+ nearby-swim, float, hike, relax
A spacious living room with a ceiling fan, a herringbone-patterned floor, and a large window with sheer curtains.

13. 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, (46 reviews)
"We enjoyed a great stay!"
United States
Heather A.
The price is €231
includes taxes & fees
14 Sept - 15 Sept
Vineyard Ridge Farmhouse • 3BR • 2BA • Vineyard View • Fire pit •
A living room with a sofa, armchair, coffee table, and a rug.

14. Pet-friendly 2BR with fenced yard

Pet-friendly 2BR with fenced yard
Saint James
9.8 out of 10, Exceptional, (27 reviews)
"Great stay, great accommodations, very clean place to stay. "
United States
Jake B.
The price is €213
includes taxes & fees
13 Sept - 14 Sept
Pet-friendly 2BR with fenced yard
A modern living room with a grey sofa, a wooden coffee table, and a flat-screen TV mounted on the wall.

15. 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
9.8 out of 10, Exceptional, (58 reviews)
"Great location right off the interstate. Nice fenced yard to let kids and/or pets play in. Great working AC and comfortable beds and sofas."
United States
Charles M. McClurg
The price is €127
includes taxes & fees
14 Sept - 15 Sept
The James Stay on Historic Route 66 • minutes away from Wineries & Restaurants
A modern kitchen with dark cabinetry, a stainless steel sink, a microwave, and a stove.

16. Spacious 3BR near downtown St. James

Spacious 3BR near downtown St. James
Saint James
9.6 out of 10, Exceptional, (34 reviews)
"Clean place, location was great!"
United States
Eileen G.
The price is €223
includes taxes & fees
14 Sept - 15 Sept
Spacious 3BR near downtown St. James
A modern kitchen with grey cabinets, a central island, and a dining area with brown chairs.

17. 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, (33 reviews)
"My wife and I stayed here for our anniversary. It was so clean and was exactly what we needed."
United States
John R.
The price is €181
includes taxes & fees
13 Sept - 14 Sept
Get Cozy in the Country - The Cottage on Luca Hill
A kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

18. Large home, Pet friendly

Large home, Pet friendly
Union
9.6 out of 10, Exceptional, (40 reviews)
"This is the second time we have stayed at this home. Great place. Thank you for the hospitality."
United States
Nadine I.
Large home, Pet friendly
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.

19. 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
8.0 out of 10, Very good, (1 review)
"Very clean, great rural view, plenty of towels and things for a group. Fun stay."
United States
Karigan C.
Delightful 3-bedroom house with AC in charming Davisville many close attractions
A bedroom with a bed, a chair, a door, a painting, and a window with curtains.

20. Comfy house minutes from Hwy 44, grill on deck, smart TV, fish, float nearby

Comfy house minutes from Hwy 44, grill on deck, smart TV, fish, float nearby
Saint James
The price is €156
includes taxes & fees
14 Sept - 15 Sept
Comfy house minutes from Hwy 44, grill on deck, smart TV, fish, float nearby
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

Greenlight Inn & Suites

Greenlight Inn & Suites

10/10 Excellent
"Quiet place. It's a motel so you can drive up to the door if you are on the 1st floor. They accept dogs for a fee and you get a 1st floor room. Breakfast was very good and staff super friendly!"
Shelly 1-night trip
Posted 1 day ago
Greenlight Inn & Suites

Find out more about Bourbon

Bourbon Holiday Homes information

Number of reviews
261
Accommodation
80 Holiday Homes
Lowest Price
€126
Highest Price
€582