Vacation Homes in Trimble County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Trimble County holiday homes

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

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)
"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 HK$662
HK$1,785 total
includes taxes & fees
10 Jan - 11 Jan
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Property grounds
Spectacular waterfront house!

Spectacular waterfront house!

Spectacular waterfront house!
Prospect
9.6 out of 10, Exceptional, (88)
"Beautiful location!"
United States
Ann B.
Spectacular waterfront house!
Smart TV
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!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (54)
"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$818
HK$1,737 total
includes taxes & fees
21 Jan - 22 Jan
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Terrace/patio
Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.2 out of 10, Wonderful, (5)
The price is HK$643
HK$1,374 total
includes taxes & fees
10 Jan - 11 Jan
Cozy Tiny House in Scottsburg
Fridge, microwave, oven, stovetop
Madison's Only YURT Experience

Madison's Only YURT Experience

Madison's Only YURT Experience
Madison
9.2 out of 10, Wonderful, (11)
"We had an amazing stay at this yurt! The inside was so cute, spacious and clean. We enjoyed relaxing in the hot tub and being entertained by the goats. "
United States
Christine U.
Madison's Only YURT Experience
Outdoor dining
Red comfy cottage

Red comfy cottage

Red comfy cottage
Madison
10.0 out of 10, Exceptional, (83)
"This was our 2nd time staying at this great property. The interior of the house is very welcoming. The backyard sitting area was my favorite. Morning coffee in the private patio was a great way to start the day. "
United States
Cathy B.
Red comfy cottage
Exterior
Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Shelbyville
Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Smart TV
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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, (38)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is HK$904
HK$1,953 total
includes taxes & fees
21 Jan - 22 Jan
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior
Enchanting, energizing, and enjoyable!

Enchanting, energizing, and enjoyable!

Enchanting, energizing, and enjoyable!
Buckner
10.0 out of 10, Exceptional, (92)
"Great stay, great place. "
United States
Tyler R.
Enchanting, energizing, and enjoyable!
Exterior
Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (5)
"This new cabin was clean, in nature. Great communication with host."
United States
Hamilton
Maple Cozy Cabin at Lost Trails
Interior
The Kentucky Spirit Retreat - Norton Commons

The Kentucky Spirit Retreat - Norton Commons

The Kentucky Spirit Retreat - Norton Commons
Louisville
9.8 out of 10, Exceptional, (9)
"Great house & area to stay with a larger group. Place is great & relatively close (~25 mins) to the track & airport. Will look to stay there again next year."
United States
Joseph S.
The Kentucky Spirit Retreat - Norton Commons
Exterior
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (77)
"Interesting property!"
United States
Donald R.
The price is HK$4,548
HK$9,119 total
includes taxes & fees
12 Jan - 13 Jan
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Private kitchen
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!

Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!

Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Madison
9.4 out of 10, Exceptional, (3)
"Cozy, fun get away close to downtown yet secluded enough to feel like you had privacy. "
United States
Raena E.
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Terrace/patio
Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!
Louisville
9.8 out of 10, Exceptional, (8)
"Beautiful home with a lovely location. The owner has many interesting pieces in the home that add to the unique, comfortable, spacious, relaxing atmosphere. The home is not only clean, it is organized and stocked with extras. We loved our five day stay and wish it was longer. Easy location to get to all the area attractions with the quiet of a country setting with a lake."
United States
Barb C.
Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!
Fridge, microwave, oven, stovetop
The Norton Commons Lavish

The Norton Commons Lavish

The Norton Commons Lavish
Louisville
10.0 out of 10, Exceptional, (9)
"Great location in a great neighborhood."
United States
Steve O.
The Norton Commons Lavish
Terrace/patio
Family/Pet-Friendly Riverside Home w/Amazing Views

Family/Pet-Friendly Riverside Home w/Amazing Views

Family/Pet-Friendly Riverside Home w/Amazing Views
Prospect
9.0 out of 10, Wonderful, (22)
"My husband and our pups had a wonderful vacation and enjoyed our stay at the Riverview House! The deck is 100% amazing and seeing riverboats, barges, party boats and even 3 eagles was great! The house is a little small, but we spent most of the time outdoors anyway. Great spot!"
United States
Kris B.
Family/Pet-Friendly Riverside Home w/Amazing Views
Interior
Charming 3-bedroom house in lovely downtown Madison.

Charming 3-bedroom house in lovely downtown Madison.

Charming 3-bedroom house in lovely downtown Madison.
2.0 star property
Madison
9.4 out of 10, Exceptional, (11)
"The house was clean and well furnished. Perfect for a weekend stay. "
United States
Leann L.
Charming 3-bedroom house in lovely downtown Madison.
Smart TV, printers
The Norton Commons Luxe

The Norton Commons Luxe

The Norton Commons Luxe
Louisville
10.0 out of 10, Exceptional, (41)
"Great place!! We had so much fun. Went for the louder than life concert with my 17 year old for his birthday and it was better that the pictures.. very cool house!!!"
United States
Maggie S.
The Norton Commons Luxe
Fridge, microwave, oven, stovetop
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is HK$740
HK$1,144 total
includes taxes & fees
13 Jan - 14 Jan
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Interior
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Madison
9.4 out of 10, Exceptional, (27)
"We enjoyed our stay very much. I would not recommend for families with small children because Jefferson Street is a very busy street. "
United States
Denise M.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Trimble County Hotel Reviews

Comfort Inn Madison near Clifty Falls

Comfort Inn Madison near Clifty Falls

10/10 Excellent
"Loved our stay!"
Katherine 2-night trip
Posted 1 day ago
Comfort Inn Madison near Clifty Falls

Find out more about Trimble County

Trimble County Vacation Homes information

Number of reviews
640
Accommodation
156 Vacation Homes
Lowest Price
HK$1,144
Highest Price
HK$9,119

Explore a world of travel with Expedia