Vacation rentals in Trimble County

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Top-rated vacation rentals in Trimble County

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Guest favorite

Farm stay in Campbellsburg

5.0 out of 5 average rating, 22 reviews

Tiny Home in Amish Country

Our Tiny Home sits on our farm called, Tenacity. It is a separate home attached to our home by a wrap around porch. Originally built for my father and his wife, the Tiny House is 800 sqft located on 70 rolling acres of north central Kentucky. This farm has a rhythm that will slow your heart rate, clear your lungs, and revive your spirit. Fireflies light your summer evening under the night sky. Amish families in their black buggies smile and greet you as you pass them on the road. LGBTQ+safe zone

Jun 19 – 26

ﺩ.ﺇ350 per night

Guest favorite

Apartment in Madison

4.99 out of 5 average rating, 201 reviews

Rivers Edge-Historic Hunger House-Upstairs-Madison

A unique blend of historic character and contemporary comfort! Floor to ceiling windows, amazing staircase and hardwood flooring with modern kitchen & bathroom, this UPSTAIRS unit with private entrance will be your oasis. The balcony, w/view of the Ohio river, is perfect for early morning coffee or relaxing after a busy day of touring Madison. WELCOME to the River's Edge! Extended stay (week-mo) discounts 21%-49%. Rent one or both floors (See "River's Edge II-listing) SEND INQUIRY FOR PRICING

Jan 17 – 24

ﺩ.ﺇ342 per night

Guest favorite

Apartment in Madison

5.0 out of 5 average rating, 273 reviews

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, a laundry room and a furnished white kitchen will all be appreciated. Carefully, the historic charm is blended within. You will soon see why the entire building is award winning! This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the Midwest”.

Jul 28 – Aug 4

ﺩ.ﺇ662 per night

Guest favorite

Loft in Madison

4.92 out of 5 average rating, 84 reviews

The Atlas

This spacious upstairs loft is located in beautiful Downtown Madison, Indiana. Our 1880's property is only 1 block from Main St. and 2 blocks to the riverfront. We are close to the Heritage Trail, scenic Vaughn Drive, wineries, brewery, antique shops, restaurants, and many more local attractions and festivals, as well as, only 4 miles from Clifty Falls State Park. This is a great place if you are looking to get away with your significant other, a girls/guys trip or taking the family hiking.

Apr 10 – 17

ﺩ.ﺇ467 per night

Guest favorite

Tiny home in Milton

4.85 out of 5 average rating, 78 reviews

The Rustic River Retreat.

A perfect getaway in a Brand New home. This Tiny Home was built BIG. It features 1 bedroom with Queen size mattress. The bathroom is equipped with 36” walk in shower, full size toilet, and Washer and Dryer. The Kitchen comes equipped with a cooktop stove, air fryer microwave, Blender, Keurig Coffee maker, large refrigerator, you have access to all basic kitchen needs. Living room couch converts to a full size bed. Easy River Access for kayaking and fishing. Outdoor seating and grill!

Feb 9 – 16

ﺩ.ﺇ487 per night

Guest favorite

Home in Milton

5.0 out of 5 average rating, 16 reviews

The Madison-Milton Cabin

Welcome to the Madison Milton Cabin. Enjoy a unique, peaceful setting just 5 minutes from Downtown Madison. Enjoy the great shopping, dining, and entertainment and finish your day relaxing next to a cozy outdoor fire. If you love sunsets you will love the views from the cabin. The house features a loft bedroom with comfy adjustable bed. The bathroom includes an oversized soaking Tub/Shower and the main living room includes a queen size pull out couch. Stay connected with high speed internet.

Sep 22 – 29

ﺩ.ﺇ570 per night

Guest favorite

Home in Bedford

4.99 out of 5 average rating, 187 reviews

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 160 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Dec 25 – Jan 1

ﺩ.ﺇ508 per night

Guest favorite

Loft in Madison

4.85 out of 5 average rating, 280 reviews

Historic Madison Spa Retreat perfect location

Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.

Dec 17 – 24

ﺩ.ﺇ319 per night

Guest favorite

Home in Milton

4.9 out of 5 average rating, 145 reviews

Milton Hillton. River front home near Madison.

Riverfront with stunning views of the Ohio River and downtown Historic Madison, IN. Located 1 mi. from Madison and 3 mi. from Clifty Falls State Park. Madison boasts a vibrant cultural district with shopping, dining, festivals, art and live music. Spacious outdoor pavilion included is great for relaxing, cookouts, watching the river roll by and fabulous sunsets. Includes plenty of seating, gas grill, fire pit, outdoor speakers and cornhole boards for your enjoyment.

May 5 – 12

ﺩ.ﺇ670 per night

Superhost

Loft in Madison

4.86 out of 5 average rating, 14 reviews

East Main Lofts - Farmhouse 204

Welcome to Farmhouse Loft — 204, nestled in the charming downtown of the river-town of Madison, Indiana. This thoughtfully designed loft captures the essence of traditional farmhouse charm while offering modern luxuries for a comfortable stay. This fully renovated historic building brings modern amenities to the character of the old. Walk to all the best shops Madison has to offer, ride golf carts along the river, or hike through Clifty Falls state park.

Nov 18 – 25

ﺩ.ﺇ418 per night

Guest favorite

Cabin in La Grange

4.98 out of 5 average rating, 156 reviews

Running Creek Log Cabin

Our cabin is about 6 miles to dock your boat onto the Ohio River. A 15 minute drive into downtown Lagrange for more shopping including food and boutiques. We are 30 drive into Louisville and 1 hour 15 min. drive to Cincinnati Ohio. It is on a 5 acre property and attached by a driveway to a home that we call Southwest Retreat that is on airbnb and 5 acres. We have a security camera on the outside of the house on the front porch facing the driveway.

May 7 – 14

ﺩ.ﺇ1,253 per night

Guest favorite

Farm stay in Campbellsburg

5.0 out of 5 average rating, 12 reviews

Enjoy the country life at our Charming Farm House

Charming Farmhouse located only 3 1/2 miles off I-71, convenient to Louisville, KY and historic Madison, IN. After spending the day on the Bourbon Trail, or at the horse races at Churchill Downs or Keeneland, come home to the peace and beauty of the farm. You can grill out, play corn hole, then make s'mores around the fire pit. Bring your vinyl records or play some of ours on our vintage Magnavox hifi stereo. Come enjoy the country life!

May 29 – Jun 5

ﺩ.ﺇ590 per night