Holiday rentals with outdoor seating in Trimble County

When I was growing up in Madison, I always wondered what it would be like to live above one of the Main Street stores. The Magnolia on Main finally gave me that experience. Over the years we have stayed in many inns and B and Bs near Madison, but this is our new favorite! It’s beautiful, spacious, spotless, and well equipped. Everything we might want to eat or do is within walking distance. We can’t wait to go back!

The home was spacious and very well kept. It was decorated well and felt homey from the moment we walked in. We love the closeness to downtown because we like to walk everywhere in Madison. Our host was very responsive and friendly. There was a lovely snack basket and some custom mugs for us to keep. It is those small touches that really make guests feel welcome. We can’t wait to visit again!

This was our third time staying at this beautiful historical, peaceful home. Great place to walk or bike and sit on the porch and watch the barges go by.

great place to stay. parked my car off street under a carport and never moved it. The river walk along the mighty Ohio was one block away and good shopping, restaurants and historic architecture best seen on foot was right there. house was clean and they thought of all the little details to make a comfortable stay. Well equipped kitchen. would definitely stay again. Also friendly neighbors and area

Absolutely wonderful place. My son and I had a wonderful time visiting the city . Beautiful,clean and so charming. We will definitely be back again.

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.

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!

The little pink house was an incredible place to stay. The cleanest Airbnb I’ve ever stayed at. Location was incredible to downtown and the river. Ashton and Addison went above and beyond when I asked for their help on a birthday surprise upon arrival. Great host and great spot. If I come back to Madison this is where I’ll be staying.

we celebrated our 10 yr anniversary. we wanted seclusion and peace and thats what we got! the indoor pool is connected to your room the giant windows allowed for a clear view of the beautiful surroundings. pool was super clean and well maintained the hot tub was the same. Sandy is an incredible host and we have plans of returning every yr to celebrate our anniversary ❤️

We rented this space plus the attached pillow and paddock inn for our entire family and it was awesome! The owners go above and beyond to make you feel welcome. The place is fully stocked with everything you need and more. The pigs and horses were also great fun for the kids!

Love the place! 5 mins to downtown Madison and the river. The place was just as described, great amenities, clean, picturesque and had a cute very friendly cat outside

The dragonfly suite was the perfect home away from home. After a long day on the road this was the perfect place to land. All the amenities you need, adorable decor, and the comfiest bed! Even though it’s a close knit neighborhood, our space still felt very private. Tammy was a fabulous and communicative host, who obviously puts a ton of thought into the details of her space. Extremely walkable to riverfront, shops, restaurants, bars, etc. Madison is such a cool town! We hope to come back and visit again. Thanks Tammy!

This location is very close to downtown but you feel like your way out in the country.

This property and the host and family ARE AMAZING!!!!!! They were very accommodating, flexible, kind, responsive, and most importantly the property IS AS DESCRIBED and more! You seriously can beat the Norton's Common area! There is a lake 1 block away, a connected bakery, and tons of playground areas for kids! The wrap around balcony is a amazing touch! We will definitely be returning soon!

Great place will be back

Brandon and his team were hugely communicative via text, which is actually my preference, and I appreciated his assistant really helping me out w a specific ask that I had, Kayla went above and beyond, big kudos to her!!! Would *absolutely* stay there again if I ever make it back to the Derby!