A river surrounded by dense forest, with people swimming and standing on the banks.

Vacation Homes in Trimble County

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Our top choices for Trimble County vacation homes

1. 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, (80 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

2. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (21 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is AED 312
AED 531 total
includes taxes & fees
16 Nov - 17 Nov
Sassafras Woodland Cabin at Lost Trails

3. Charming 3-bedroom house in lovely downtown Madison.

Charming 3-bedroom house in lovely downtown Madison.
Madison Historic District
9.6 out of 10, Exceptional, (34 reviews)
"Beautiful century home within perfect walking distance of the riverfront."
United States
Rysa L.
Charming 3-bedroom house in lovely downtown Madison.

4. Madison's Only YURT Experience

Madison's Only YURT Experience
Madison
9.2 out of 10, Wonderful, (11 reviews)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
United States
Nicole E.
Madison's Only YURT Experience

5. Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8

Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8
Prospect
9.6 out of 10, Exceptional, (112 reviews)
"Loved the riverfront view and had everything we needed!"
United States
Ashley S.
Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8

6. The Wadsworth in National Historic District of Madison, Indiana.

The Wadsworth in National Historic District of Madison, Indiana.
Madison Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Perfect location for a relaxed few days with a dear friend! Loved it!"
United States
Patti B.
The Wadsworth in National Historic District of Madison, Indiana.

7. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Madison Historic District
10.0 out of 10, Exceptional, (32 reviews)
"Great stay and beautiful house. The location was really outstanding and many restaurants, boutiques, and coffee shops were within walking distance. "
United States
Stephanie B.
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

8. 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 Historic District
9.6 out of 10, Exceptional, (39 reviews)
"Great location very clean"
United States
Karen G.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

9. East End River Retreat: Dogs Welcome!

East End River Retreat: Dogs Welcome!
Madison Historic District
10.0 out of 10, Exceptional, (39 reviews)
"We had a delightful stay at East End River Retreat. Clean, well furnished, an overall wonderful experience in spite of the town being without electricity!"
United States
Melissa Y.
East End River Retreat: Dogs Welcome!

10. Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays

Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays
Crestwood
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay. Host was responsive and friendly. The house was adorable and well kept. Everything worked great and had a great stocked coffee bar! Would recommend."
United States
Shawna C.
Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays

11. Rock & Roll Riverhouse | Pool | Mins to Louisville

Rock & Roll Riverhouse | Pool | Mins to Louisville
Utica
10.0 out of 10, Exceptional, (2 reviews)
"The house and accommodations were amazing! Great host and great house!"
United States
Sandy Z.
Rock & Roll Riverhouse | Pool | Mins to Louisville

12. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Madison
10.0 out of 10, Exceptional, (22 reviews)
"The house had everything you might need, was nicely furnished,and was clean. It has a nice outdoor area with a fire pit and hot tub. It was a very enjoyable stay."
United States
Terry S.
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

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

Peaceful getaway centrally located just min. from Madison and Belterra casino.
Vevay
9.6 out of 10, Exceptional, (48 reviews)
"A nice family weekend getaway!"
United States
Kim M.
Peaceful getaway centrally located just min. from Madison and Belterra casino.

14. 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
9.6 out of 10, Exceptional, (55 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is AED 533
AED 1,005 total
includes taxes & fees
19 Nov - 20 Nov
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

15. NEW! Historic, Walk to Main St, King Suites, Patio

NEW! Historic, Walk to Main St, King Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (3 reviews)
"A perfect place to stay to explore the town of Madison! The location is within walking distance to everything you need."
United States
Claire Y.
NEW! Historic, Walk to Main St, King Suites, Patio

16. Iconic Lighthouse Estate on Scenic Ohio River!

Iconic Lighthouse Estate on Scenic Ohio River!
Prospect
10.0 out of 10, Exceptional, (1 review)
"What an amazing property and an amazing owner to work with. We will definitely be looking to rebook should the property have vacancy on our next trip to Louisville."
United States
Sean S.
The price is AED 624
AED 2,263 total
includes taxes & fees
30 Nov - 1 Dec
Iconic Lighthouse Estate on Scenic Ohio River!

17. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Good location, well stocked with essentials."
United States
Leslie W.
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

18. Alterra:Slees 8,Steps to Main St,Serene

Alterra:Slees 8,Steps to Main St,Serene
Madison Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Home is beautiful. Great stay."
United States
Ben M.
Alterra:Slees 8,Steps to Main St,Serene

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

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Shelbyville
9.8 out of 10, Exceptional, (7 reviews)
"Everything was exceptional from the host, the home and all the amenities! We will definitely book again!"
United States
Jessica P.
Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

20. Bungalow on Main!!

Bungalow on Main!!
Madison Historic District
9.8 out of 10, Exceptional, (42 reviews)
"It was a great place to stay. Clean and very pretty."
United States
Amy Z.
Bungalow on Main!!
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

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