
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)

2. Sassafras Woodland Cabin at Lost Trails
Sassafras Woodland Cabin at Lost TrailsMadison Township
10.0 out of 10, Exceptional, (21 reviews)
The price is AED 312
AED 531 total
includes taxes & fees
16 Nov - 17 Nov

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)

4. Madison's Only YURT Experience
Madison's Only YURT ExperienceMadison
9.2 out of 10, Wonderful, (11 reviews)

5. Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8
Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8Prospect
9.6 out of 10, Exceptional, (112 reviews)

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)

7. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main StMadison Historic District
10.0 out of 10, Exceptional, (32 reviews)

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 BathMadison Historic District
9.6 out of 10, Exceptional, (39 reviews)

9. East End River Retreat: Dogs Welcome!
East End River Retreat: Dogs Welcome!Madison Historic District
10.0 out of 10, Exceptional, (39 reviews)

10. Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended Stays
Crestwood Home w/Hot Tub - Bourbon Trail - Quiet - Family - Extended StaysCrestwood
9.8 out of 10, Exceptional, (16 reviews)

11. Rock & Roll Riverhouse | Pool | Mins to Louisville
Rock & Roll Riverhouse | Pool | Mins to LouisvilleUtica
10.0 out of 10, Exceptional, (2 reviews)

12. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grillMadison
10.0 out of 10, Exceptional, (22 reviews)

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)

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)
The price is AED 533
AED 1,005 total
includes taxes & fees
19 Nov - 20 Nov

15. NEW! Historic, Walk to Main St, King Suites, Patio
NEW! Historic, Walk to Main St, King Suites, PatioMadison Historic District
10.0 out of 10, Exceptional, (3 reviews)

16. Iconic Lighthouse Estate on Scenic Ohio River!
Iconic Lighthouse Estate on Scenic Ohio River!Prospect
10.0 out of 10, Exceptional, (1 review)
The price is AED 624
AED 2,263 total
includes taxes & fees
30 Nov - 1 Dec

17. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio RiverMadison Historic District
9.0 out of 10, Wonderful, (2 reviews)

18. Alterra:Slees 8,Steps to Main St,Serene
Alterra:Slees 8,Steps to Main St,SereneMadison Historic District
10.0 out of 10, Exceptional, (2 reviews)

19. Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20
Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20Shelbyville
9.8 out of 10, Exceptional, (7 reviews)

20. Bungalow on Main!!
Bungalow on Main!!Madison Historic District
9.8 out of 10, Exceptional, (42 reviews)
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

HavenPointe Inn & Suites
10/10 Excellent
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