Holiday rentals in Trimble County

4.99 out of 5 average rating, 238 reviews

Flat in Madison

Rivers Edge-Historic Hunger House-Upstairs-Madison

LiziRating, 5 stars1 week ago

The apartment is just as described, in a beautifully restored old home. Everything was spotless and comfortable, and there were all sort of extra conveniences like extra toiletries and snacks. Parking/check in and check out were super easy with clear directions, and the location worked well for us- right by the river and close to restaurants and shops. We especially appreciated the coupons to local businesses. The hosts responded quickly to my questions and were very pleasant. Recommend when you’re in the adorable and quaint town of Madison!

5 out of 5 average rating, 25 reviews

Flat in Madison

Livery Loft: BEST location!

SurabhiRating, 5 stars1 week ago

Our stay at Suzie and Ron’s place was nothing short of exceptional. We were celebrating my dad’s birthday, and they went above and beyond to make it incredibly special — from the cake and cookies to the thoughtful decorations, every detail was so meaningful. My dad was overjoyed, and we’ll cherish the memories we made there forever. They also made everything so comfortable and welcoming for my young son. He absolutely loved the toys, the book, and especially the homemade muffins — such a sweet and personal touch. It genuinely felt like staying with family. This has been, without a doubt, the best Airbnb experience we’ve ever had. Suzie’s warmth and care made us feel completely at home, and we’d love to return in the future. Thank you again, Suzie, and please pass on our heartfelt thanks to Ron as well!

5 out of 5 average rating, 304 reviews

Flat in Madison

Stablemaster’s Quarters/ Best downtown location!

DebbieRating, 5 stars2 months ago

This is a great location to the downtown shops just being a block from Main Street. There is a lot of parking on the street but we didn’t have to worry we would have a spot when we arrived. Suzie placed orange cones in spots just in front of the Airbnb for us. When we arrived she had our favorite music playing and homemade cookies on the counter to welcome us. I had guests coming and going all weekend and I had asked if she would provide extra linens to change out and she was happy to do that. I felt she could have just as easily said that’s why there is a washer and dryer there for that purpose. She made us warm blueberry muffins the morning of checkout and made sure we were comfortable with the checkout procedure. Highly recommend this place, and you won’t find a nicer host! She made our stay comfortable and cozy and had a fully stocked refrigerator of different waters and coffees, even snacks and breakfast foods. This lady deserves 10 stars!!!!!

4.95 out of 5 average rating, 42 reviews

The Nature House

StephanieRating, 5 stars1 month 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.

4.99 out of 5 average rating, 210 reviews

Home in Bedford

Atoka Farms

GlennRating, 5 stars2 days ago

Kevin’s place is peaceful with beautiful wooded surroundings. The home is perfect. We enjoyed a campfire one night and relaxing fires in the fireplace the nights it rained. Kevin provides everything you’ll need and more for a comfortable stay. A little off the beaten path but that’s what makes it peaceful and it’s still easy to get to everything in the area. Loved it!

4.97 out of 5 average rating, 29 reviews

Main Street Retreat Prime Location 3 Bedroom Top1%

MindyRating, 5 stars1 month ago

We loved our stay at Marcy‘s! It was the perfect walking distance from all the local shops on Main Street! Marcy’s kitchen was well equipped with all the things we needed to make breakfast, as well as coffee. The space was very clean, and looked like the pictures provided in the listing! Marcy provided multiple recommendations of things to do in the area and provided clear communication upon check-in and checkout. We would love to come and stay again next year!

4.98 out of 5 average rating, 131 reviews

Riverview Historical Retreat

KevinRating, 5 stars2 days ago

Great place to stay if you are visiting the Madison, IN area. House was really comfortable and has a great little backyard. Only a few blocks from multiple restaurants, bars and shops. Madison is a nice little town with lots of things to do.

4.98 out of 5 average rating, 104 reviews

Townhouse in Madison

209 King Beds, River View, Deck, Parking

ShellyRating, 5 stars2 weeks ago

Stayed for a girls weekend. We each had our own room and every place we wanted to go was within walking distance. We rented a golf cart but didn't really need it because of the location; however, the golf cart was super fun! Beautiful place. It's a tri-level with bedrooms in the lowest level, stairs to the main space, and stairs to the other two bedrooms. Absolutely gorgeous.

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Other great holiday rentals in Trimble County

5 out of 5 average rating, 7 reviews

The Magnolia on Main hosted by Swell Stay

TriciaRating, 5 stars1 week ago

We had a great girls weekend! Madison is a super cute, friendly, eclectic community. This home was super adorable, super comfy, and a great place to have a comfy, fun, relaxing girls weekend.

Campsite in Pendleton

4.86 out of 5 average rating, 49 reviews

Camping at Hones Pointe campground and park

SeanRating, 5 stars21 months ago

Oh, nothing about the property was bad. I really appreciated the early check-in, but I was just unclear on what spots were available or if they were reserved. So I took a chance and I hope I did not cross any lines. The river was beautiful, the spots were well-maintained, I only wish they had electric at the place that I chose. It did have outlets but no electric hook ups. All in all a great stay and I will come back just to relax.

4.97 out of 5 average rating, 36 reviews

Cottage in Madison

Cheerful 3-Bedroom cottage with fireplace.

LoriRating, 5 stars1 month ago

The house and location were beautiful and Brian was incredibly helpful and responsive. We can’t wait to come back!

5 out of 5 average rating, 13 reviews

Home in Bethlehem

1872 Bethlehem Home w/ View of Ohio River!

TinaRating, 5 stars1 month ago

The home was just as described. It was an historical old house, with a lot of interesting history that posted in the house telling you about it. Great getaway, beautiful scenery, quiet/peaceful. Maybe can rent it again in the future.

4.79 out of 5 average rating, 47 reviews

Home in Vevay

Little Lamb Retreat at the river

KristiRating, 5 stars2 days ago

We were looking for a place for a girls weekend to enjoy a hot tub, play games and just catch up. The house fit the bill! The house was very comfortable and exactly as described. We were very excited to find a large coffee pot and a Kuerig! Many times it’s all in the details when you stay at an Airbnb, and this place hit the mark in the details. Bill was very responsive with messages and responded very quickly. Highly recommend if you want a comfy house that offers a great porch for coffee and evening drinks.