Vacation Rentals in Trimble County

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Top Vacation Rentals in Trimble County

Cabin in Milton

10.0 out of 10, Exceptional, (19)
"The cabin was just as described online it's very quiet and was the perfect getaway "
United States
christy m.
Cozy Cabin Madison Indiana

Vacation Home in Louisville

9.8 out of 10, Exceptional, (76)
"Interesting property!"
United States
Donald R.
$1,060 nightly
The price is $1,230
Dec 8 - Dec 9
Total with taxes and fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Vacation Home in Prospect

9.6 out of 10, Exceptional, (86)
"Great location with views of the river. "
United States
Patrick G.
Spectacular waterfront house!

Cabin in Madison

10.0 out of 10, Exceptional, (53)
"Great day, we loved the cabin!"
United States
Mark C.
Rustic cabin just outside of Madison!

Apartment in Madison

10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
$161 nightly
The price is $185
Dec 8 - Dec 9
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Vacation Home in 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.
$217 nightly
The price is $250
Dec 8 - Dec 9
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Apartment in Madison

2.0 star property
10.0 out of 10, Exceptional, (14)
"Great little place. Location was exceptional. "
United States
Andrew P.
$146 nightly
The price is $168
Dec 8 - Dec 9
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Apartment in Prospect

10.0 out of 10, Exceptional, (6)
"Amazing views of the Ohio River and unique design with a lot of character. It was the perfect amount of communal space and privacy for our family of four.Only negatives were some deferred maintenance (leaking fridge, missing remotes, dirty air filter and some outdoor lights out)"
United States
David A.
$361 nightly
The price is $419
Dec 8 - Dec 9
Total with taxes and fees
Enchanting Riverfront Nest! Beautiful 3-Bedroom Lighthouse with Panoramic Views!

Vacation Home in Louisville

10.0 out of 10, Exceptional, (9)
"Great location in a great neighborhood."
United States
Steve O.
The Norton Commons Lavish

Apartment in Madison

10.0 out of 10, Exceptional, (61)
"This was the best place I have ever stayed. The place was amazing and the hospitality exceeded expectations. I would definitely recommend staying here. "
United States
Adam K.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Apartment in Madison

8.8 out of 10, Excellent, (10)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
$133 nightly
The price is $142
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

Vacation Home in Madison

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot walkable to downtown Madison & the river area. Appreciated how well-stocked the kitchen, bathroom, and laundry were. And being able to bring a pet was a big plus."
United States
Chelsea C.
Charming 2-bedroom house with a river view in wonderful Madison

Vacation Home in Prospect

9.0 out of 10, Wonderful, (22)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
United States
Rachel R.
Family/Pet-Friendly Riverside Home w/Amazing Views

Vacation Home in 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.
$224 nightly
The price is $228
Dec 8 - Dec 9
Total with taxes and fees
Sleeps 4, Rustic, Secluded

Vacation Home in Madison

2.0 star property
9.4 out of 10, Exceptional, (11)
"Great old home and cool neighborhood. "
United States
Randy S.
Charming 3-bedroom house in lovely downtown Madison.

Cabin in Madison

10.0 out of 10, Exceptional, (312)
"The cleanest, quietest, well-kept cabin you will ever see!"
United States
David F.
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Vacation Home in Scottsburg

9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
$154 nightly
The price is $172
Dec 29 - Dec 30
Total with taxes and fees
Cozy Tiny House in Scottsburg

Vacation Home in 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.
$314 nightly
The price is $361
Dec 8 - Dec 9
Total with taxes and fees
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Cabin in Madison

10.0 out of 10, Exceptional, (102)
"Close enough to be convenient to local attractions, out enough to be mostly quiet. "
United States
Garry B.
Stoney Creek - Sit back and unwind

Cabin in Henryville

10.0 out of 10, Exceptional, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
$423 nightly
The price is $478
Dec 8 - Dec 9
Total with taxes and fees
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
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

Find out more about Trimble County

Discover your perfect Trimble County vacation rental with Expedia

How many vacation rentals are available in Trimble County?


Expedia has plenty of vacation rentals to choose from in and around  Trimble County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Trimble County?


The selection of Trimble County vacation rentals we have selected for you start as low as $142 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Trimble County?


Vacation rentals in Trimble County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Trimble County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Trimble County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Trimble County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Trimble County?


Find vacation rentals in Trimble County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Trimble County.  


What amenities are available in a vacation rental in Trimble County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Trimble County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Trimble County?   


Everytime is a great time to head to Trimble County! Staying in a Trimble County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Trimble County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Trimble County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Trimble County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Trimble County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.