Holiday Rentals in Trimble County

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Featured Holiday Rentals in Trimble County

Cozy Cabin Madison Indiana
Cozy cabin interior with a central seating area, wooden coffee table, and a mounted deer head above the sofa.

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (16)
"The cabin was just as described online it's very quiet and was the perfect getaway "
Cozy Cabin Madison Indiana
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Modern kitchen with stainless steel appliances, light grey cabinetry, and a black and white patterned rug.

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (5)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Enjoy cooking and socializing in this kitchen with a central island and bar stools, featuring stainless steel appliances and a pendant light fixture.

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

9.8 out of 10, Exceptional, (33)
"Clean, comfortable home with everything needed for our stay. "
The price is €218
includes taxes & fees
3 Aug - 4 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Enjoy serene lakeside views from the porch of this charming lakeside retreat, where you can relax and unwind amidst lush greenery.

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

10.0 out of 10, Exceptional, (190)
"Great getaway. View is fantastic!!! Location with plenty of privacy!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Enjoy cooking in this well-appointed kitchen with a stainless steel sink, wooden countertop, and range hood.

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

9.8 out of 10, Exceptional, (70)
"This place was a perfect stay for my bachelor party! There was a ton of room, the host was very responsive with any questions and it had everything we needed. Highly recommend! "
The price is €997
includes taxes & fees
10 Aug - 11 Aug
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Stoney Creek - Sit back and unwind
Enjoy cooking in this inviting kitchen with a central island, oven, and window overlooking the surrounding landscape.

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (89)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind
Spectacular waterfront house!
Outdoor spa tub

Spectacular waterfront house!

9.6 out of 10, Exceptional, (76)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!
Rustic Cabin at Lost Trails
Guests can enjoy a secluded retreat in this cabin, surrounded by mature trees and featuring a spacious porch with a railing.

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (8)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Compact kitchen with modern design, featuring an oven, microwave, and window.

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (50)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Rustic cabin just outside of Madison!
Relax in a spacious room with a four-poster bed, wooden headboard, and a ceiling fan.

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (41)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Enjoy serene lake views from this waterfront property with a dock and inviting entrance.

Beautiful views and sunrises overlooking the water. Spacious home with elevator.

9.6 out of 10, Exceptional, (5)
"Great house that has room for extended family and kids for the week. Great time playing pickleball at the owners house as well "
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Relaxing Country Getaway
Cozy space with a fireplace, leather sofa, and wooden panel walls, perfect for relaxing.

Relaxing Country Getaway

9.4 out of 10, Exceptional, (33)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Relax in a comfortable living space with a sectional sofa and large mirror.

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

10.0 out of 10, Exceptional, (43)
"This is the second time staying at this unit. Next weekend, we are going down and staying in the upstairs loft. Looking forward. Always a great time staying with Suzie. Highly recommend."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
The Wadsworth in National Historic District of Madison, Indiana.
Enjoy cooking in this well-equipped kitchen with an oven and stovetop.

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (51)
"We absolutely loved our stay in Madison at the Wadsworth House! You couldn't ask for a nicer place to stay for a quiet get away!"
The Wadsworth in National Historic District of Madison, Indiana.
Bungalow on Main!!
Traditional home with a symmetrical facade, featuring a decorative front door and a small porch area.

Bungalow on Main!!

9.8 out of 10, Exceptional, (14)
"This place was great. The wife and I need a little getaway to relax and recharge. Our stay here was perfect for that. Nice amenities and the private hottub was really relaxing. Will definitely book here again. "
Bungalow on Main!!
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Escape to a serene forest setting with a fire pit and seating area.

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

10.0 out of 10, Exceptional, (304)
"My family and I truly enjoyed our stay. We love coming here it has all the amenities that added to our comfort. Hosts were very accommodating which was really appreciated. "
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop

Modern Nature Cabin | Private Escape in the Forest

The price is €195
includes taxes & fees
31 Jul - 1 Aug
Modern Nature Cabin | Private Escape in the Forest
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Cozy cabin features a dining area, seating area, and living room with a fireplace and TV.

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

10.0 out of 10, Exceptional, (146)
"Our family had a spectacular stay at the Stone Creek. Our kids (7, 3, 2 yo) had a blast playing pingpong, board games, and hot tub. Place was clean and we felt home. We’ll definitely come back!"
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fully equipped kitchen with microwave, stove, sink, and refrigerator.

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (4)
"Riverside Retreat is a must stay! It is a great location and exactly as described. Highly recommend. We will be back!"
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Charming 2-bedroom house in downtown Historic Madison with WiFi, AC, laundry
Compact kitchen with a refrigerator, oven, and washing machine/dryer. Dining area with a table and chairs.

Charming 2-bedroom house in downtown Historic Madison with WiFi, AC, laundry

2.0 star property
9.6 out of 10, Exceptional, (11)
"We had a nice stay. The house was clean and comfortable. The location is in walking distance to the river and Main Street. Check in process was smooth. "
Charming 2-bedroom house in downtown Historic Madison with WiFi, AC, laundry
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

La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd

La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd

10/10 Excellent
"The stay was okay. The service to correct thumbs was done quick. The TV didn't work and we didn't get our assigned run that i paid a security dossier for. BUT the kindness and professionalism that i was shown was great. "
anthony l 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd