
Holiday rentals with outdoor seating in Madison
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Madison
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Madison outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Main Street Retreat
Marcy's place was the perfect location for a girl's weekend trip. We were able to park our car and then walk everywhere the rest of our stay. Easy to walk to all the shops and restaurants on main street in Madison. We enjoyed sitting on the covered back patio as well. Would definitely stay here again. It's a beautiful place that was very clean and comfortable.

Kick Back Watching The River Go By
Martine and Janice were both fantastic from the time we booked to the time we left with communicating with us. They provided clear instructions on how to gain access to the home, some interesting history on the area and home, activities to do in the area, and instructions for check out. The home was very clean. The floor plan was nice with large open living/dining space facing the river. Watching the barges on the river was pretty cool and there is a nice deck with comfy deck furniture or two comfy chairs inside you can enjoy watching them from!

Spacious home in a quaint small town setting
This was my 5th time of staying at the Dillsborough Inn. It is always a fantastic place to stay. Wonderful home that is well kept. Beautiful inside and out. Peaceful quiet safe neighborhood. Pam is a wonderful host. She makes everything so easy and is well organized. A very friendly lady that is always ready to answer any questions. I am looking forward to staying here again next year.

Annies Fabulous Federal house
Beautiful place! My spouse and I stayed here with our 2 pups for 4 nights and it felt like a home away from home. Very cozy, and it was so clean when we showed up. The king bed was SO comfy, I wanted to take it with us when we left. I slept incredible. She left great instructions, and checking in was easy. When we visit back, we only hope this place will be available to book again!!

Milton Hillton. River front home near Madison.
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!

Secluded Country Home in Historic Hoosier Hills
Our stay was very nice and had a great time. We were able to feel right at home. Was great the 7 of us. Was great to have stocked kitchen and big pots and pans to be able to cook the full meal in. The deck in the back was our place most of the time. View was beautiful and wild life was seen several times. Mark and Janet were great to work with and communicate with. We had a WiFi issue but Mark jumped on it immediately to get issue taken care of. I felt like I knew them a long time. Thank you so much. We will be back again.

Watchmaker Place in Historic Madison District
I booked this place for a girls' weekend, and we all loved the house. The design, amenities, and location were great—close to Main Street and the Riverwalk. It was clean and well-stocked with everything we needed.. Christopher, the host was responsive and friendly to communicate with. I highly recommend this place to anyone looking for a wonderful space and atmosphere.

Charming shotgun in the heart of downtown Madison
I wish I could give more than 5 stars. This property is perfect, and the hosts are amazing. They make us feel welcome every time we visit, and I think this may be our 6th time...maybe more... staying at this great house. The hosts always greet us with information before we arrive and always thank us when we check out. This house isn't just a place to stay, it is a great base for an amazing experience. We love sitting out on the porch in the evening. The people who pass by are very friendly and the vibe is super relaxing. We can't wait to go back.
Apartment rentals with outdoor seating

Family-friendly 2BR Hot Tub & Pool
awesome place, close to town but secluded, pool and hot tub did not disappoint, cool layout plenty of seating, good ac, loved the projector and surround sound we watched 2 family movies and had a great time, kids loved the love sacs. As fellow hosts nice work

Sugar Maple ~ Charming Guest House in Madison
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 Regatta Room (Unit 3) - Ohio River Views
The area was amazing with shops, restaurants & museums. Short drive to downtown. The walks along the Ohio River were amazing! Would stay here again if coming to Madison! 😊

Dragonfly Suite
Tamara was great to work with. My wife and her friend stayed at the small home and they absolutely loved it. It was my wife’s birthday and Tamara took time out to do some sidewalk chalk art to celebrate my wife. Place was clean and easily accessible to downtown. Would definitely book here again.

Sugar Berry ~ Charming Guest House in Madison
This location is very close to downtown but you feel like your way out in the country.

Rivers Edge-Historic Hunger House-Upstairs-Madison
Stayed 3 nights at River's Edge and wish it would've been 3 weeks. Everything was wonderful - the walk-ability, view, cleanliness, entertainment options, comfort, etc. Madison was a delightful surprise all the way around. Angie's suggestions of what to do and where to eat were also too notch! Couldn't have asked for a better trip and can't wait to be back! The upstairs apartment does connect to the downstairs with an open staircase. There was a family staying downstairs when we were, which wasn't an issue in the slightest - I just didn't quite realize how connected the two were before checking in. We kept the box fans on that were provided in the unit and doors shut to maintain some privacy!

Studio Apartment w/ Beautiful View!
The apartment is beautiful and extremely homey. Having the deck to sit on in the mornings was so nice. Would definitely recommend staying here if you’re visiting Aurora!

Pleasant Ridge Bliss
Great place will be back
Quick stats about holiday rentals with outdoor seating in Madison
Total rentals
60 properties
Nightly prices starting at
$108 AUD before taxes and fees
Total number of reviews
4.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Indianapolis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Lexington Holiday rentals
- Bloomington Holiday rentals
- Dayton Holiday rentals
- Williamstown Holiday rentals
- Nashville Holiday rentals
- Nashville Holiday rentals
- Gatlinburg Holiday rentals
- Chicago Holiday rentals
- Western North Carolina Holiday rentals
- Apartment rentals Madison
- Rentals with a fire pit Madison
- Pet-friendly rentals Madison
- Rentals with a washing machine and dryer Madison
- Rentals with a fireplace Madison
- Kid-friendly rentals Madison
- Rentals with a patio Madison
- Cabin rentals Madison
- Rentals with pools Madison
- Rentals with outdoor seating Jefferson County
- Rentals with outdoor seating Indiana
- Rentals with outdoor seating United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Ark Encounter
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Creation Museum
- Big Four Bridge
- Louisville Slugger Field
- Kentucky Derby Museum
- Louisville Slugger Museum & Factory
- Perfect North Slopes
- Valhalla Golf Club
- Muhammad Ali Center
- Versailles State Park
- Angel's Envy Distillery
- Charlestown State Park
- Waterfront Park
- River Run Family Water Park
- Turtle Run Winery
- Kentucky Science Center
- Evan Williams Bourbon Experience
- Falls of the Ohio State Park
- Big Spring Country Club
- At The Barn Winery
- Hurstbourne Country Club
- Frazier History Museum