Holiday Rentals in Trimble County

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Rentals in Trimble County

Cozy Cabin Madison Indiana
Living area

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (16)
"Cabin was relatively secluded, in a pretty location and exactly as described. 5 minutes from downtown Madison Indiana which is a beautiful old river town. Host was exceedingly accommodating and gracious and the property has everything you need. Will definitely book again. "
Cozy Cabin Madison Indiana
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Property grounds

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (180)
"Beautiful, stunning views!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Interior

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (63)
"My sorority sisters and I booked this property for a weekend together - we had a lovely time, even though weather caused us to cut the trip short. The host was very responsive and understanding of our leaving ahead of schedule. The property was a great size for our group and we had plenty of space to spread out but still be together. "
The price is €1,163
includes taxes & fees
18 Feb - 19 Feb
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (23)
"This place is awesome! It’s the best place to stay in Madison, IN. Well decorated and has everything you need. The host Suzie goes over and above to make sure your stay is memorable. Great location in town. We already have future dates reserved and will add more in 2025. "
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Stoney Creek - Sit back and unwind
Terrace/patio

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (70)
"Was a beautiful cabin wonderful hot tub awesome views loved the cows "
The price is €219
includes taxes & fees
23 Feb - 24 Feb
Stoney Creek - Sit back and unwind
Rock & Roll RiverHouse: Pool Table, Mins to Louisville!
Exterior

Rock & Roll RiverHouse: Pool Table, Mins to Louisville!

10.0 out of 10, Exceptional, (1)
"We had a great time spending Thanksgiving at the Rock & Roll Riverhouse! The property was clean, spacious and entertaining for our kids. We had 7 adults and 2 kids and had enough room for us all. It was a great location and was an easy drive into Louisville. "
Rock & Roll RiverHouse: Pool Table, Mins to Louisville!
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (22)
"Had a good time "
The price is €219
includes taxes & fees
18 Feb - 19 Feb
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Spectacular waterfront house!
Property grounds

Spectacular waterfront house!

9.6 out of 10, Exceptional, (75)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!
The Norton Commons Lavish
Property grounds

The Norton Commons Lavish

10.0 out of 10, Exceptional, (4)
"We had 2 families stay here for Thanksgiving and it worked out great - tons of space for everyone to spread out. I will say the house is very advanced so took us a bit to figure out the lights and thermostat! Location is great - walking distance to some cafes and restaurants and cute boutiques. "
The Norton Commons Lavish
Family/Pet-Friendly Riverside Home w/Amazing Views
Terrace/patio

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (19)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
Family/Pet-Friendly Riverside Home w/Amazing Views
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Exterior

The Waterfall Suite Place + Walkout! Both Overlook Waterfall!

9.8 out of 10, Exceptional, (40)
"We were hit with a snowstorm the day we were to arrive. Our crew all lives within a few hours but roads got pretty bad pretty quickly and we all arrived much later than expected, and even with 4 wheel drive none of us were able to get our cars up the driveway. The owners were kind enough to shuttle us (all 13 of us!) and our belongings up to the house in their big beast of a truck as we all arrived throughout the evening. Very much appreciated! It was a wonderful stay and we all had a great...
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Secluded Country Home in Historic Hoosier Hills
Exterior

Secluded Country Home in Historic Hoosier Hills

10.0 out of 10, Exceptional, (117)
"This was an excellent place we loved it!"
Secluded Country Home in Historic Hoosier Hills
Livery Loft: our other BEST downtown location! Award winning! Come see why.
Aerial view

Livery Loft: our other BEST downtown location! Award winning! Come see why.

10.0 out of 10, Exceptional, (11)
"This place. This owner. This was far beyond our expectations ! The location is beautiful. Comfortable . Spotless. Safe. There is no stone left unturned in this property. The owner, Suzie, is absolutely lovely. She makes the stay so comfortable and makes sure that you know where everything is . The town is fantastic and we had the time of our lives. Already looking forward for our next trip ! Thank you !!"
Livery Loft: our other BEST downtown location! Award winning! Come see why.
#207 King Suites, River Views, Deck, Downtown
Interior

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (29)
"We had a 5 couples get away for one evening and stayed in the house. A great view of the river and perfect location for walks to the shops, Park and restaurants. We plan on staying here again in the future! "
The price is €518
includes taxes & fees
18 Feb - 19 Feb
#207 King Suites, River Views, Deck, Downtown
Sonshine Cabin a great place to enjoy the Holidays with family or friends
Exterior

Sonshine Cabin a great place to enjoy the Holidays with family or friends

10.0 out of 10, Exceptional, (288)
"This was our second time to stay at Sonshine Cabin. It is very clean! Decorated super cute and the kitchen is well appointed. Owners are great with communication, as well. We will definitely come again."
Sonshine Cabin a great place to enjoy the Holidays with family or friends
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.6 out of 10, Exceptional, (7)
"Place was clean, downtown, and what pictures shown. Owner was kind and understanding. "
Bungalow on Main!!
#209 Kings, River View, Deck, Bicentennial Park
Fridge, microwave, oven, stovetop

#209 Kings, River View, Deck, Bicentennial Park

10.0 out of 10, Exceptional, (55)
"Nice property and well equipped. We had no problem cooking full breakfast and full dinner for 8 people. Nice location for walking to places in town."
The price is €518
includes taxes & fees
18 Feb - 19 Feb
#209 Kings, River View, Deck, Bicentennial Park
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA
Property grounds

THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA

9.8 out of 10, Exceptional, (45)
"We had a wonderful family Christmas in January with 8 adults and 3 little ones. Loved the open floor plan and all of the glass overlooking the waterfalls and woods. Electric fireplace is inviting and even puts out heat! Our hosts generously left the Christmas tree and decorations up for our family. Our crew loved the hot tub (quite large), the oven that goes to 550 (for pizza), the large bowls and utensils for cooking, and the beautiful scenery for walks, play, and photos. "
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA
Carol’s Cabin in the Woods in Historic Hoosier Hills
Aerial view

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (29)
"We wanted to get away for a bit and we hit the jackpot with this place! It was very clean, well stocked and a beautiful property. You can definitely tell that the property is well kept and maintained. We loved hiking the trails with our dogs. The scenery is beautiful! If you want a peaceful, relaxing experience to unplug and enjoy God’s creation, or quality time, this is your place! We definitely will return to in the future!"
Carol’s Cabin in the Woods in Historic Hoosier Hills
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Outdoor spa tub

Peaceful getaway centrally located just min. from Madison and Belterra casino.

9.0 out of 10, Wonderful, (16)
"Had a nice relaxing time"
Peaceful getaway centrally located just min. from Madison and Belterra casino.
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.
Don't see what you're looking for?
See all available properties in Trimble County
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free