Holiday Rentals in Trimble County

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Our top choices for Trimble County holiday rentals

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

Holiday Home in Pendleton

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
9.8 out of 10, Exceptional, (62)
"Host was responsive to all messages. The small home we stayed in was so cozy and clean. Directions on how to get there were clear and easy to follow. 10/10 would recommend."
United States
Haley V.
The price is €200
includes taxes & fees
29 Dec - 30 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Exterior
Cabin on the Ridge: The Sequel

Cabin in Madison

Cabin on the Ridge: The Sequel
10.0 out of 10, Exceptional, (17)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is €193
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin on the Ridge: The Sequel
TV, fireplace, DVD player
Cabin on the Ridge Su

Cabin in Madison

Cabin on the Ridge Su
10.0 out of 10, Exceptional, (15)
"Peaceful relaxing stay. Will go back."
United States
Wendy P.
The price is €211
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin on the Ridge Su
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Holiday Home in Madison

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
9.8 out of 10, Exceptional, (53)
"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 €194
includes taxes & fees
2 Jan - 3 Jan 2026
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
The Artist’s A-Frame

Holiday Home in Madison

The Artist’s A-Frame
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is €195
includes taxes & fees
4 Jan - 5 Jan 2026
The Artist’s A-Frame
Miscellaneous
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cottage in Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
2.0 star property
The price is €140
includes taxes & fees
29 Dec - 30 Dec
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior
Cozy Tiny House in Scottsburg

Holiday Home in Scottsburg

Cozy Tiny House in Scottsburg
9.6 out of 10, Exceptional, (4)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is €154
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg
Interior
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

Apartment in Madison

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
9.6 out of 10, Exceptional, (14)
"Perfect little space for our weekend getaway. Great location, everything was very clean and up to date. "
United States
brad h.
The price is €138
includes taxes & fees
4 Jan - 5 Jan 2026
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Interior
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Holiday Home in Charlestown

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
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 €129
includes taxes & fees
10 Jan - 11 Jan 2026
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Holiday Home in Hanover

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
9.8 out of 10, Exceptional, (37)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is €220
includes taxes & fees
29 Dec - 30 Dec
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

Holiday Home in Sparta

Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
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 €323
includes taxes & fees
29 Dec - 30 Dec
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
Outdoor dining
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Apartment in Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
2.0 star property
The price is €132
includes taxes & fees
18 Jan - 19 Jan 2026
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Holiday Home in Madison

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
10.0 out of 10, Exceptional, (14)
"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.
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Pool
Cozy Cottage in Smithsonian's of American Gardens!

Apartment in Prospect

Cozy Cottage in Smithsonian's of American Gardens!
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 €173
includes taxes & fees
28 Jan - 29 Jan 2026
Cozy Cottage in Smithsonian's of American Gardens!
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Apartment in Madison

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is €199
includes taxes & fees
4 Jan - 5 Jan 2026
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Microwave, oven, stovetop, dishwasher
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

Holiday Home in Madison

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
2.0 star property
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown

Holiday Home in Charlestown

Emerald Lake Retreat 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 €398
includes taxes & fees
30 Dec - 31 Dec
Emerald Lake Retreat Charlestown
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

Holiday Home in Madison

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
Exterior
Sleeps 4, Rustic, Secluded

Holiday Home in Lexington

Sleeps 4, Rustic, Secluded
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 €191
includes taxes & fees
29 Dec - 30 Dec
Sleeps 4, Rustic, Secluded
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Cabin in Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown 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 €252
includes taxes & fees
28 Jan - 29 Jan 2026
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
"Had a great experience from the moment we checked-in till we checked out. 5 star service. "
Vamsi Krishna 1-night trip
Posted 2 days ago
Drury Inn & Suites Louisville North

Find out more about Trimble County

Holiday Homes in Trimble County

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