Trimble County Holiday Rentals

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Featured Trimble County Holiday Rentals

Fridge, microwave, oven, stovetop
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Pendleton
9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
The price is HK$685
HK$1,819 total
includes taxes & fees
13 Dec - 14 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Exterior
Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel

Madison
10.0 out of 10, Exceptional, (17)
"This was an excellent property and had everything we needed for a relaxing girls night!!! The cabin was very clean and in a quiet, secluded area which was perfect for enjoying nature!!!"
United States
Samantha B.
The price is HK$872
HK$1,629 total
includes taxes & fees
8 Dec - 9 Dec
Cabin on the Ridge: The Sequel
TV, fireplace, DVD player
Cabin on the Ridge Su

Cabin on the Ridge Su

Madison
10.0 out of 10, Exceptional, (15)
"Peaceful relaxing stay. Will go back."
United States
Wendy P.
The price is HK$872
HK$1,817 total
includes taxes & fees
10 Dec - 11 Dec
Cabin on the Ridge Su
Property grounds
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Madison
9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
The price is HK$592
HK$1,004 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Exterior detail
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

2.0 star property
Madison
The price is HK$617
HK$1,246 total
includes taxes & fees
14 Dec - 15 Dec
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Interior
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charlestown
10.0 out of 10, Exceptional, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is HK$740
HK$1,144 total
includes taxes & fees
8 Dec - 9 Dec
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Exterior
Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg

Scottsburg
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is HK$615
HK$1,343 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is HK$666
HK$1,437 total
includes taxes & fees
8 Dec - 9 Dec
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
Madison
10.0 out of 10, Exceptional, (14)
"Great little place. Location was exceptional. "
United States
Andrew P.
The price is HK$981
HK$1,307 total
includes taxes & fees
9 Dec - 10 Dec
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is HK$981
HK$1,898 total
includes taxes & fees
18 Dec - 19 Dec
The Artist’s A-Frame
Pool
Cozy Cottage in Smithsonian's of American Gardens!

Cozy Cottage in Smithsonian's of American Gardens!

Prospect
10.0 out of 10, Exceptional, (1)
"Scenic horse farm. Secluded, private, and quiet. I couldn't be happier with the accommodations. Would like to return when in the area."
United States
Darlene N.
The price is HK$637
HK$1,432 total
includes taxes & fees
17 Dec - 18 Dec
Cozy Cottage in Smithsonian's of American Gardens!
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Madison
9.8 out of 10, Exceptional, (51)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is HK$973
HK$1,943 total
includes taxes & fees
8 Dec - 9 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Hanover
9.8 out of 10, Exceptional, (33)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is HK$904
HK$1,962 total
includes taxes & fees
8 Dec - 9 Dec
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Fridge, microwave, oven, stovetop
Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest

Hanover
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is HK$723
HK$1,748 total
includes taxes & fees
11 Dec - 12 Dec
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown

Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
The price is HK$973
HK$3,615 total
includes taxes & fees
12 Dec - 13 Dec
Emerald Lake Retreat Charlestown
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Madison
10.0 out of 10, Exceptional, (12)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
The price is HK$1,183
HK$2,811 total
includes taxes & fees
8 Dec - 9 Dec
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Exterior
Sleeps 4, Rustic, Secluded

Sleeps 4, Rustic, Secluded

Lexington
8.0 out of 10, Very good, (4)
"The cabin and property were very clean and easy to find. We loved the back yard for chilling around after we got back from the event we were attending. Host was very friendly and had good communication. Will stay again if we are back in the area! "
United States
Nicole C.
The price is HK$852
HK$1,777 total
includes taxes & fees
8 Dec - 9 Dec
Sleeps 4, Rustic, Secluded
Exterior
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

Sparta
9.8 out of 10, Exceptional, (9)
"Wonderful vacation home. Very clean, great host that was very helpful. "
United States
Ashley C.
The price is HK$1,394
HK$3,105 total
includes taxes & fees
8 Dec - 9 Dec
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

Madison
9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is HK$1,253
HK$2,838 total
includes taxes & fees
9 Dec - 10 Dec
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Madison
9.6 out of 10, Exceptional, (20)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
The price is HK$1,401
HK$2,256 total
includes taxes & fees
8 Dec - 9 Dec
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
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 Trimble County Hotel Reviews

Drury Inn & Suites Louisville North

Drury Inn & Suites Louisville North

10/10 Excellent
"Excellence in all aspects of delivery. Facility, staff, execution, all top shelf."
Chris 1-night trip
Posted 4 days ago
Drury Inn & Suites Louisville North