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

Vacation Rentals in Trimble County

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Our top choices for Trimble County vacation rentals

A wooden cabin with a porch, a staircase, and a deck.

1. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is ￥13,538
￥24,806 total
includes taxes & fees
Aug 30 - Aug 31
Sassafras Woodland Cabin at Lost Trails

2. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is ￥15,927
￥27,554 total
includes taxes & fees
Sep 2 - Sep 3
Maple Cozy Cabin at Lost Trails
A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

3. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
10.0 out of 10, Exceptional, (17 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is ￥8,601
￥30,364 total
includes taxes & fees
Sep 1 - Sep 2
Modern cabin very close to scenic riverfront walks
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

4. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is ￥15,927
￥27,554 total
includes taxes & fees
Aug 30 - Aug 31
Walnut Secluded Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

5. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
The price is ￥15,927
￥27,554 total
includes taxes & fees
Aug 30 - Aug 31
Mulberry Secluded Cabin at Lost Trails

6. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Very close to downtown restaurants and shopping. The trails out back were nice and relaxing to walk on. The property was quiet and relaxing. Perfect size for my wife and I and our 12 pound dog. The dog loved the trails and kept us busy on his walks."
United States
Dean
The price is ￥15,911
￥29,286 total
includes taxes & fees
Aug 31 - Sep 1
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

7. 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, (72 reviews)
"Great house just outside of historic Madison. Easy access to the river . Home is beautifully decorated and great place for a getaway. Many shops to visit in Madison ."
United States
John H.
The price is ￥17,058
￥35,919 total
includes taxes & fees
Sep 2 - Sep 3
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

8. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison
9.0 out of 10, Wonderful, (14 reviews)
"Nicely restored building. Charming decor"
United Kingdom
Rana W.
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

9. 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, (49 reviews)
"Close to downtown Madison and Clifty Falls, this place had everything we needed to visit the area and relax I'm the evening."
United States
Maggie D.
The price is ￥18,491
￥40,131 total
includes taxes & fees
Aug 30 - Aug 31
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A cozy room with a bed, a chair, a sofa, and a small table.

10. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is ￥14,334
￥27,474 total
includes taxes & fees
Aug 31 - Sep 1
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

11. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is ￥17,520
￥29,569 total
includes taxes & fees
Sep 1 - Sep 2
Cedar Rustic Cabin at Lost Trails

12. Romantic 1 BR Retreat on the edge of woods with private hot tub

Romantic 1 BR Retreat on the edge of woods with private hot tub
Madison
The price is ￥26,518
￥34,892 total
includes taxes & fees
Sep 13 - Sep 14
Romantic 1 BR Retreat on the edge of woods with private hot tub
A cozy wooden cabin interior with a sofa, a dining table, and a TV.

13. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is ￥22,616
￥40,510 total
includes taxes & fees
Sep 7 - Sep 8
Cabin on the Ridge: The Sequel
A covered porch with a wooden door, potted plants, and a metal railing.

14. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (39 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
The price is ￥19,283
￥38,207 total
includes taxes & fees
Aug 30 - Aug 31
The Artist’s A-Frame
A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

15. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is ￥19,272
￥36,903 total
includes taxes & fees
Aug 30 - Aug 31
Cabin on the Ridge
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

16. The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (45 reviews)
"Loved the whole place and all the little touches. It was super cozy and location wise is close to everything. We will definitely be stay again. "
United States
Hannah S.
The price is ￥17,058
￥34,087 total
includes taxes & fees
Aug 30 - Aug 31
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A residential property with a red door, a small front yard with grass and shrubs, and a neighboring church with a steeple.

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

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
The price is ￥18,635
￥37,182 total
includes taxes & fees
Aug 30 - Aug 31
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
An outdoor patio with a hot tub, a fire pit, and string lights.

18. "Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison
10.0 out of 10, Exceptional, (21 reviews)
"we had a good time. enjoyed our visit"
United States
Douglas S.
The price is ￥21,701
￥57,742 total
includes taxes & fees
Aug 31 - Sep 1
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
A covered patio with a door, two wicker chairs, and string lights.

19. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
The price is ￥13,149
￥28,106 total
includes taxes & fees
Aug 29 - Aug 30
Cozy Tiny House in Scottsburg
An outdoor patio with a hot tub, a fire pit, and string lights.

20. "Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8

"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
Madison
9.6 out of 10, Exceptional, (15 reviews)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is ￥21,874
￥57,941 total
includes taxes & fees
Aug 31 - Sep 1
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
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

Hillside Inn

Hillside Inn

10/10 Excellent
"Clean; great view; friendly staff; close to downtown"
Stacy 1-night trip
Posted 12 hours ago
Hillside Inn

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