House vacation rentals in Trimble County

Find and book unique houses on Airbnb

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Popular amenities for Trimble County house rentals

House rentals with a pool

Home in Louisville
4.83 out of 5 average rating, 6 reviews

The Getaway!

LaTaireRating, 5 stars1 week ago
The home was beautiful. Me and my family felt very comfortable there! We were able to cook family dinners, play the games that were made available by the host, and enjoy the deck in the back. We did have to spend a couple hours cleaning the pool ourselves due to the debris, etc., which is one of the reasons we were interested in the home, otherwise we really wouldn’t have gotten in it. The hosts were responsive when we asked for a net. By the time we had gotten in the pool, it was cooler outside, but we made the best of it and had fun in it! It definitely wasn’t all a loss! Lots of floaties & pool toys were available! I loved the decor! The beds were comfortable! The pillows were better than a hotel’s, definitely! There’s 2 smart TVs, you can choose to sign into your streaming services or not because they have some readily available for you. Lastly, I couldn’t use the jets in the tub because they weren’t clean, But I could still enjoy a bath without them. I would book again, though!
Top guest favorite
Home in Prospect
5 out of 5 average rating, 6 reviews

Bourbon Trail, Pools, Downtown, Watch Hill, Pets

JaimeRating, 5 stars2 weeks ago
This home and the area is gorgeous, the area has a whimsical feel with the beautiful homes. Several locals eateries that were delicious and within walking distance. Beds were comfortable with plenty of extra linens. Bathrooms were spotless, wash cloths would be a nice item to have but we did not see any provided. The garage parking was a nice added bonus, would love to stay again. Great home, great location and great host!!
Guest favorite
Home in Hanover
4.83 out of 5 average rating, 12 reviews

The Hanover O-Asis

PatsiRating, 5 stars2 months ago
This home looked new, very clean and open. The extras, games, snacks, coffee were great. we could walk to Hanover College which was why we were there. Road noise mentioned in the listing was so minimal, we really never noticed. This home is beautiful and very comfortable. Will absolutely go back when we visit grandaughter in college!
Home in Goshen
4.73 out of 5 average rating, 11 reviews

The Boathouse: A Peaceful Paradise

KyleRating, 5 stars8 months ago
This place was amazing. Both Wes and Rachel were extremely accommodating and had everything we needed ready. The place was clean and stocked with everything to make our stay perfect. The boat ride down the river made for a memorable highlight. We will be back!
Top guest favorite
Home in Prospect
5 out of 5 average rating, 106 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

BradRating, 5 stars1 week ago
We loved our stay at this super-convenient home-away-from-home. Very convenient, safe, and walkable. The host provided numerous welcomed conveniences and tailored our stay for our young daughter. I literally have not encountered a more courteous host yet.
Top guest favorite
Home in Prospect
5 out of 5 average rating, 12 reviews

CIRCO LOCO - uNCommon Stay

Leigh AnneRating, 5 stars3 months ago
I had a fantastic stay at circo loco! The space was exactly as described—clean, comfortable, and in a great location. walking distance to everything you need and more ! The check-in process was seamless, and amie was incredibly responsive and helpful throughout my stay. They even left a welcome treat! I would absolutely stay here again and highly recommend it to anyone visiting or even just needing a weekend of fun!
Top guest favorite
Home in Goshen
5 out of 5 average rating, 68 reviews

Relaxing River Retreat with Private Pool

MaryRating, 5 stars7 months ago
Absolutely perfect! I would say this AirBnb is one of the best that we’ve stayed at. Amazing views of the river. Kristen was very responsive and had everything we needed at the house. The kitchen was stocked with everything you need to cook meals. Beds were comfortable and there were plenty of towels and hot water! I definitely recommend Kristen’s house! I know I didn’t want to leave!
Guest favorite
Home in Crestwood
4.95 out of 5 average rating, 19 reviews

Private 5 acre A frame

KevinRating, 5 stars9 months ago
Great outdoor space and great entertainment in the basement!

Weekly house rentals

Guest favorite
Home in Madison
4.97 out of 5 average rating, 58 reviews

Glenda’s Overlook

KaitlinRating, 5 stars2 weeks ago
house was amazing! beautifully decorated. great views!
Guest favorite
Home in Madison
5 out of 5 average rating, 10 reviews

Riverside Retreat 2 - Steps to the River & Main St

GailRating, 5 stars4 weeks ago
Great location and easy walk to town and the Ohio river. Grandson wanted to walk to "Ohio" alot. Close to Clifty Falls. We would stay here again if back in the area.
Top guest favorite
Home in Madison
4.95 out of 5 average rating, 57 reviews

Bicentennial Park View

TylerRating, 5 stars3 weeks ago
Beautiful home, with a ton to do within walking distance. We couldn’t have been happier with our stay. Madison is historically beautiful and this home made it feel like we were residents.
Guest favorite
Home in Madison
4.95 out of 5 average rating, 42 reviews

The Nature House

StephanieRating, 5 stars2 months ago
Jennifer’s place was a perfect stay for our family of seven. We had a kid with us and one of the rooms upstairs is connected to another room that has a futon. There isn’t a door that separates the two rooms but we were fine with that. It was sunny and nice to be able to sit on the back patio. We rented a golf cart and took that around town (designated areas). The town is very walkable and in the summer months, with everything open, I can imagine it being lively. We took a walk along the Ohio River (which we walked to) and that was nice. Kitchen also had what we needed to make meals. We would definitely stay here again.
Top guest favorite
Home in Madison
5 out of 5 average rating, 89 reviews

The Row House

AngieRating, 5 stars3 weeks ago
We’ve traveled all over the world (even to London & Paris, just like the themed rooms 😉), and this is one of the best Airbnb’s we’ve ever stayed in! Hilary’s attention to detail & thoroughness is amazing! The beds are super comfortable, the shower is wonderful, and we loved the fire bowl in the back! The location is unmatched- perfect for walking to the shops & restaurants nearby and a very short drive for hiking at Clifty Falls! We loved dinner at Red on Main (the dates appetizer was Michelin-star worthy) and seeing live music both nights at Mad Paddles Brewstillery (worth going for their beer wall and their ranch (best I’ve ever had!) alone! We also loved the 12,000 step hike we did at Clifty Falls- some of the most stunning views in Indiana! 🙂 Hilary & Tony’s Airbnb is the best of the best!
Guest favorite
Home in Milton
4.91 out of 5 average rating, 166 reviews

Milton Hillton. River front home near Madison.

MichelleRating, 5 stars4 weeks ago
We loved our stay here! The pavilion was the highlight of our time. We spent many nights around the fire taking in the scenery. Unfortunately we got rained out the last few nights, but staying in was cozy and there were cards and a few games provided. Not much to do in Milton, but plenty to do right over the bridge in Madison, IN and in surrounding areas. The hosts seem very friendly and responsive. Would definitely stay here again!
Top guest favorite
Home in Madison
4.93 out of 5 average rating, 30 reviews

The Baltmore

JudithRating, 5 stars3 weeks ago
This cottage is charming and you feel at home the minute you cross the threshold. It's tastefully decorated and updated without losing the historic charm. We loved the location which is off the main drag but easily walkable to the downtown shops. The back deck was a quiet place to enjoy breakfast and the perfect weather we were blessed with. Everything was clean, fresh, and spotless. We will definitely stay again when we're in the area! Loved it!
Top guest favorite
Home in Bedford
4.99 out of 5 average rating, 212 reviews

Atoka Farms

ElizabethRating, 5 stars1 week ago
Kevin's home is perfectly suited for peace and respite. Beautiful trees, nature, a quiet bubbling creek and a breathtaking view of sunsets over the Ohio River. He thought of every detail to make our stay comfortable. What a hidden gem!

Private house rentals

Guest favorite
Home in Madison
4.97 out of 5 average rating, 58 reviews

Glenda’s Overlook

KaitlinRating, 5 stars2 weeks ago
house was amazing! beautifully decorated. great views!
Guest favorite
Home in Madison
5 out of 5 average rating, 10 reviews

Riverside Retreat 2 - Steps to the River & Main St

GailRating, 5 stars4 weeks ago
Great location and easy walk to town and the Ohio river. Grandson wanted to walk to "Ohio" alot. Close to Clifty Falls. We would stay here again if back in the area.
Guest favorite
Home in Madison
4.95 out of 5 average rating, 42 reviews

The Nature House

StephanieRating, 5 stars2 months ago
Jennifer’s place was a perfect stay for our family of seven. We had a kid with us and one of the rooms upstairs is connected to another room that has a futon. There isn’t a door that separates the two rooms but we were fine with that. It was sunny and nice to be able to sit on the back patio. We rented a golf cart and took that around town (designated areas). The town is very walkable and in the summer months, with everything open, I can imagine it being lively. We took a walk along the Ohio River (which we walked to) and that was nice. Kitchen also had what we needed to make meals. We would definitely stay here again.
Top guest favorite
Home in Madison
5 out of 5 average rating, 89 reviews

The Row House

AngieRating, 5 stars3 weeks ago
We’ve traveled all over the world (even to London & Paris, just like the themed rooms 😉), and this is one of the best Airbnb’s we’ve ever stayed in! Hilary’s attention to detail & thoroughness is amazing! The beds are super comfortable, the shower is wonderful, and we loved the fire bowl in the back! The location is unmatched- perfect for walking to the shops & restaurants nearby and a very short drive for hiking at Clifty Falls! We loved dinner at Red on Main (the dates appetizer was Michelin-star worthy) and seeing live music both nights at Mad Paddles Brewstillery (worth going for their beer wall and their ranch (best I’ve ever had!) alone! We also loved the 12,000 step hike we did at Clifty Falls- some of the most stunning views in Indiana! 🙂 Hilary & Tony’s Airbnb is the best of the best!
Guest favorite
Home in Milton
4.91 out of 5 average rating, 166 reviews

Milton Hillton. River front home near Madison.

MichelleRating, 5 stars4 weeks ago
We loved our stay here! The pavilion was the highlight of our time. We spent many nights around the fire taking in the scenery. Unfortunately we got rained out the last few nights, but staying in was cozy and there were cards and a few games provided. Not much to do in Milton, but plenty to do right over the bridge in Madison, IN and in surrounding areas. The hosts seem very friendly and responsive. Would definitely stay here again!
Top guest favorite
Home in Madison
4.93 out of 5 average rating, 30 reviews

The Baltmore

JudithRating, 5 stars3 weeks ago
This cottage is charming and you feel at home the minute you cross the threshold. It's tastefully decorated and updated without losing the historic charm. We loved the location which is off the main drag but easily walkable to the downtown shops. The back deck was a quiet place to enjoy breakfast and the perfect weather we were blessed with. Everything was clean, fresh, and spotless. We will definitely stay again when we're in the area! Loved it!
Top guest favorite
Home in Bedford
4.99 out of 5 average rating, 212 reviews

Atoka Farms

ElizabethRating, 5 stars1 week ago
Kevin's home is perfectly suited for peace and respite. Beautiful trees, nature, a quiet bubbling creek and a breathtaking view of sunsets over the Ohio River. He thought of every detail to make our stay comfortable. What a hidden gem!
Guest favorite
Home in Madison
4.86 out of 5 average rating, 7 reviews

Little Pink House - North

AmberRating, 5 stars4 weeks ago
Love this place 🤍

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