Holiday houses in Madison

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Popular amenities for Madison holiday rentals

Stay near Madison's top sights

Clifty Falls48 locals recommend
The Red Pepperoni26 locals recommend
Lanier Mansion State Historic Site21 locals recommend
Off Broadway Tap Room20 locals recommend
Hinkle's Sandwich Shop17 locals recommend
Thomas Family Winery17 locals recommend

Other great holiday rentals in Madison

Top Guest favourite
Home in Madison
4.99 out of 5 average rating, 73 reviews

Cabin in the Holler

Hyun JiRating, 5 stars2 weeks ago
Pauline’s place was so beautiful! It had everything listed and Pauline herself was so sweet! We didn’t have to worry about privacy as the property had so much space and the check in and out process was extremely easy. It is also located close to Madison, IN which had great restaurants and a great downtown (You will need a car to get to downtown). Overall would love to stay again.
Guest favourite
Farm stay in Turners Station
5 out of 5 average rating, 5 reviews

The Lodge in Henry Co.

ShanonRating, 5 stars9 months ago
This has been an absolute fantastic place to stay. Very accommodating and responsive when needed. It certainly feels homely the minute you walk in. It has made my deployment so much better having somewhere I can relax and unwind and away from the city distractions. Highly recommended if you want quiet away from the city lights.
Top Guest favourite
Apartment in Madison
4.98 out of 5 average rating, 107 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

MelissaRating, 5 stars1 week 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!
Top Guest favourite
Cabin in Rising Sun
4.99 out of 5 average rating, 77 reviews

Cheerful 2 BR cabin on 48 acres with ponds/firepit

AngelaRating, 5 stars3 weeks ago
We really, really enjoyed this property even though it rained & stormed every day. The view is so gorgeous! We actually enjoyed watching the storms out the large windows that overlook the property, the large pond and rolling hills. Watching the deer meandering around as they fed and the turkeys chasing each other was better than watching TV. This property is so peaceful. On nice days, there is lots to do as he says in the description…pontoon & paddle boat on the pond, a fire pit area, the hot tub, corn hole, comfortable deck, and just walking the property. The home was spotless and very comfortably appointed. We could not think of one thing we would have wanted that wasn’t already provided. So many towels, blankets, kitchen utensils, etc. Beautiful and tasteful decor. Comfortable beds. We traveled with another couple & there was plenty of room. Jim was very responsive from beginning to end. If we could give more than 5 stars, we would. I’m sure anyone would love their stay.
Guest favourite
Home in Sparta
4.98 out of 5 average rating, 65 reviews

Lake House with River Dock - Ark & Creation Museum

JamesRating, 5 stars2 months ago
This was a great place to stay. Justin was very helpful and accommodating.
Guest favourite
Home in Aurora
4.92 out of 5 average rating, 66 reviews

Unique Luxury Family Retreat

AliciaRating, 5 stars4 days ago
We had a great stay. No issues , everything went smoothly and the house was perfect!
Top Guest favourite
Home in Burlington
4.98 out of 5 average rating, 173 reviews

Kick Back Watching The River Go By

KathyRating, 5 stars3 weeks ago
Beautiful place outstanding view. Lightning storm over the river was amazing. Very clean and host were SUPER.
Top Guest favourite
Cabin in Pendleton
4.96 out of 5 average rating, 54 reviews

A Little Piece of Heaven

YazminRating, 5 stars1 week ago
A truly special stay for a truly special weekend! We stayed at A Little Piece of Heaven to celebrate my 30th birthday, and the experience exceeded every expectation. The hosts were incredibly thoughtful, communicative, and kind throughout our entire visit—from the detailed directions to the fresh eggs waiting for us on the porch. The property itself is beautiful and peaceful, with so many personal touches that made us feel right at home. One of the highlights was the farm tour—my nieces got to feed the chickens, gather eggs, and meet some of the animals. It was such a sweet experience, and I know it’s something they’ll remember forever. We truly appreciated their hospitality and openness—it made our trip feel like more than just a stay. I can’t recommend this place enough if you’re looking for a peaceful, welcoming getaway surrounded by nature and good people. Thank you again for everything!

Quick stats about holiday rentals in Madison

  • Total rentals

    120 properties

  • Total number of reviews

    7.6K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    110 properties include access to Wi-Fi

Destinations to explore

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  2. United States
  3. Indiana
  4. Jefferson County
  5. Madison