Vacation rentals with outdoor seating in Trimble County

A welcoming living area features polished hardwood floors and large windows draped with golden curtains. A modern cream sofa is complemented by colorful accent pillows, while a cozy armchair and a stylish desk provide additional seating. A decorative fireplace adds character.

5 out of 5 average rating, 87 reviews

The Row House

CindyRating, 5 stars1 month ago

The place was even more beautiful than the photos. We enjoyed the patio and fire put. The walkable location can’t be beat. It also had comfy beds and so many nice extras left by very accommodating and responsive hosts. We would definitely recommend staying here

The historic home features a classic brick exterior with intricate architectural details and large windows. A welcoming front porch is supported by white columns, enhancing the entrance. Surrounding greenery adds to the inviting atmosphere of this thoughtfully renovated property.

5 out of 5 average rating, 143 reviews

River's Edge II-Historic Hunger House-Downstairs

LaurieRating, 5 stars4 weeks ago

We loved staying at Angela’s place. The location was so convenient to walk to everything-we only used our car to go to Clifty Falls. Angela was a wonderful host and the fresh baked cookies and other treats were thoroughly enjoyed. We loved everything about the home-the comfortable bed, the high shower head, the fireplace…everything. If we ever have the opportunity to return to Madison, we will definitely stay here again!

Superhost

4.88 out of 5 average rating, 8 reviews

Riverside Retreat - Steps to the River & Main St

BrookeRating, 5 stars6 months ago

Our visit to the Kentuckiana area was unexpected and on a last minute notice. After booking and connecting with Carmer, we knew we made the perfect choice. With our stay not being a typical getaway/vacation, Carmer was very understanding of our needs, more than accommodating, and responded very quickly every time. The property was everything we needed and more. In addition to being fully stocked with the necessities and all the listed amenities, it was also beautifully decorated for Fall, making it cozy and welcoming. We were thankful for the comfortable queen size beds in all three rooms to help with restful nights. The property was perfectly located steps away from the Ohio River with benches and green spaces in one direction and charming downtown Madison's shops, restaurants, and activities in the other. The entire area is walkable and felt very safe. I highly recommend this property and host and hope to return for a vacation stay in the future.

4.95 out of 5 average rating, 42 reviews

The Nature House

StephanieRating, 5 stars3 weeks 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, 209 reviews

A spacious home is visible, framed by greenery and a gravel pathway. Several outdoor chairs are arranged around a fire pit, while the deck features a covered seating area. The two-story structure showcases large glass windows, inviting natural light into the interior.

Home in Bedford

Atoka Farms

MariaRating, 5 stars3 weeks ago

Kevin was very responsive to messages. Also I arrived late to check in but he trued to go out of his way to explain to me how to get in the property. He followed up while driving to the property. This was an amazing experience. Definitely will be going back in the summer.

A covered porch is showcased, featuring a textured floor and decorative railings. Lattice panels provide privacy while the entrance to the home is visible at the far end. Sunlight filters through the nearby trees, illuminating the space.

4.94 out of 5 average rating, 51 reviews

Bicentennial Park View

SidRating, 5 stars5 days ago

we loved the place ! it was clean well put together, nice furniture the place felt like home. it was not all ran down and beat up. there is private parking under an attached carport. so we could unload the car out of the rain. it is centrally located. there is a park across the street, another one down the block. just one block from the beautiful Ohio river. and only two blocks away from main street where there are plenty of restaurants and shops and night life. Madison indiana is a great town with plenty of historic sites and this house is a great place to stay while you visit. I highly recommend this place !!!☆☆☆☆☆ all the way across the board, we will be back !

4.92 out of 5 average rating, 26 reviews

The exterior of a charming Italianate-style townhouse is displayed, featuring a symmetrical facade with large windows adorned with black shutters. A vibrant red door adds a pop of color. Lush greenery surrounds the entrance, complementing the rustic brick exterior under a clear blue sky.

Townhouse in Madison

"Madison Manor I” By the River *Regatta Special

MichelleRating, 5 stars3 weeks ago

Madison Manor was a fun place to stay during our spring break. The house and amenities were great. We appreciated the use of the hot tub and the game room for our middle school son. This house is wonderful for people who love older homes, especially seeing how the closets looked back then and enjoying the high ceilings. No worries there is plenty of drawer space and hooks for clothing. Cyndi was attentive to our questions and proactive ensuring we understood the third room had bunkbeds and was a walkthrough to the kitchen. The location was on one side of town and between Main Street and the river walk providing a little more privacy and easy access to both. It was also closer to the bridge which was great for our day trips to Louisville, Lexington, and Cincinnati. The kitchen was great for making breakfast in the morning. If it is off-season, check for hours of stores and restaurants open in Madison during your stay. We would definitely stay here again.

Superhost

The exterior of the triplex features two levels with a light grey facade and contrasting red doors. A staircase leads to a balcony with seating, while gravel surrounds the building. Lush greenery and a hillside are visible in the background.

4.83 out of 5 average rating, 12 reviews

The Regatta Room (Unit 3) - Ohio River Views

JennyRating, 5 stars2 months ago

It was exactly like the picture.She was very responsive for a question we had.Her book of attractions & where to eat made life easy.She puts a star by the one she would recommend.There was also a bulletin board on the wall with different menus.Very clean & updated.Would recommend & go back

4.98 out of 5 average rating, 103 reviews

The spacious living area is furnished with a large sectional sofa and an ottoman, complemented by decorative pillows. A mix of historic photographs adorns the walls, while natural light enters through a large window. A desk with a lamp and a Bluetooth speaker add functionality.

Townhouse in Madison

209 King Beds, River View, Deck, Parking

ShellyRating, 5 stars6 days 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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Popular amenities for Trimble County outdoor seating rentals

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House rentals with outdoor seating

5 out of 5 average rating, 5 reviews

The Magnolia on Main hosted by Swell Stay

DrewRating, 5 stars1 month ago

This beautiful house easily accommodated all six of us women. The house was immaculate and every detail was beyond amazing! We enjoyed walking to shops, restaurants, and the Ohio River. Brantley always responded quickly and his wife provided us with a list of her favorite places to shop. The hosts went above and beyond to make this an extraordinary stay for us!

A view from the porch showcases the Ohio River, framed by leafless trees and rolling hills in the distance. A rope railing lines the edge, while a small round table and a chair are positioned in the foreground, inviting relaxation.

5 out of 5 average rating, 9 reviews

Riverside Retreat 2 - Steps to the River & Main St

JustinRating, 5 stars1 week ago

Great place and location. The neighbors around the property were friendly. I was staying there with my family while on call at the local hospital. It was very easy access to the hospital and surrounding restaurants and attractions.

5 out of 5 average rating, 13 reviews

Home in Bethlehem

1872 Bethlehem Home w/ View of Ohio River!

TinaRating, 5 stars4 weeks 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.

The exterior of a charming shotgun house is displayed, featuring exposed red brick and whitewashed walls. Two framed windows are symmetrically positioned on either side of a central door, while a flag adds a touch of character. Lush greenery is visible in the foreground.

4.97 out of 5 average rating, 38 reviews

Carpet Alley

RoyRating, 5 stars1 week ago

This is a lovely, peaceful home in the heart of Madison. Everything is extremely comfortable and well appointed, and the design touches really set it apart. I had a great weekend in Madison (Clifty Falls is absolutely beautiful by the way), and Linda’s space is the perfect base to explore the city and surrounding area. 100% would stay again

A cozy outdoor seating area features a dark wicker sectional sofa with gray cushions surrounding a glass-topped table. A yellow watering can and potted plants add touches of color, while a vibrant red umbrella provides shade. The blue exterior of the nearby house completes the inviting space.

5 out of 5 average rating, 27 reviews

The Baltmore

CaroleRating, 5 stars2 days ago

My husband and I really enjoyed our stay at The Baltmore. The house was immaculate, and the decor was so tastefully done. From the local artists artwork throughout the house, the comfortable and cozy furniture, most from local vendors and shops in Madison, and the special decorating touches that made you feel right at home. The booklet that she put together had not only great suggestions for restaurants and things to see and do in Madison but also had the history of the house. The neighborhood was very quiet and close to absolutely everything in Madison. We loved sitting out on the back deck just enjoying the pleasant evenings. Andra was an incredible host, by far one of the best I have ever dealt with on Airbnb. She was so helpful and always responded to my emails very quickly. She definitely does what it takes for you to be comfortable and feel like you're in your own home. I highly recommend it if you're planning a trip to Madison, IN.

The exterior of a historic home features a charming pink façade with white trim. Intricate woodwork adorns the porch, which is complemented by a wooden bench. A welcoming door with a decorative element is located at the center, framed by large windows.

5 out of 5 average rating, 5 reviews

Little Pink House - North

AmberRating, 5 stars2 months ago

Loved it! Return guest!

4.78 out of 5 average rating, 45 reviews

An outdoor hot tub is positioned on a wooden deck, with steam rising gently from the water. A potted arrangement of sunflowers is displayed nearby on a small table. A grassy landscape and distant trees create a serene backdrop.

Home in Vevay

Little Lamb Retreat at the river

AllieRating, 5 stars1 month ago

Everything was great Bill responded extremely quickly to our last minute getaway and we were able to bring our two fur babies!! We came here mainly for the hot tub and to get away from the busy city. It was quite peaceful and very homey. The hot tub was one of the best ones my partner and I have been in. Perfect weekend getaway so relaxing! Try Roxy Vevay bar restaurant had amazing food. The house was unique and beautiful. Would recommend going.

A historic two-story home features a gray exterior with white columns supporting the porch. Lush green landscaping includes small bushes, with a paved pathway leading to the entrance. A wrought-iron fence encloses the yard, creating an inviting outdoor space.

4.95 out of 5 average rating, 91 reviews

Watchmaker Place in Historic Madison District

Mary JoRating, 5 stars1 week ago

Great location for our visit to hike in Cliffty Falls. Nice neighborghood with beautiful old homes. Christopher's place has a very well stocked kitchen and very comfortable.

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Apartment rentals with outdoor seating

An outdoor deck features two chairs positioned beside a railing, overlooking a scenic view of the hills. Soft sunlight filters through the trees, illuminating the space and creating a peaceful ambiance for relaxation.

4.98 out of 5 average rating, 107 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

MelissaRating, 5 stars4 days ago

Pictures do not do this amazing home justice. It’s just magical. Sandy is soooo sweet and helpful. I can’t wait to go back! I felt like a Disney princess when the deer came strolling by. ❤️ peaceful beautiful surroundings and the pool is to die for! Thank you Sandy!

A cozy living area features a yellow sofa and a patterned armchair, accompanied by a soft ottoman. A guitar rests nearby, with a television positioned on a wooden stand. Colorful artwork adorns the walls, and natural light enters through windows with decorative curtains.

4.96 out of 5 average rating, 505 reviews

Dragonfly Suite

JesseRating, 5 stars1 day ago

I really appreciate that Tamara doesn't not have cleaning fees added on to her rental. it's nice to see the listed price and know that's how much it will cost.

A cozy sitting area features a richly patterned sofa alongside a red armchair. A wooden table holds reading materials. Soft light is provided by a stylish lamp, and a piece of artwork depicting the river enhances the space. Sunshine filters through a window with a blackout shade.