Top Vacation Homes in Madison County in 2026

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A clear stream with large rocks and trees in a forested area.

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Our top choices for Madison County vacation homes

A modern kitchen with grey cabinets, a black refrigerator, and a microwave.

1. "The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington

Farmington

Ben C.

AED 922 total

includes taxes & fees

15 Nov - 16 Nov

An outdoor patio area with a round table and chairs, surrounded by a stone wall.

2. The Sutton House 2 blocks from Main Street & Courthouse Square

Ironton

Craig H.

AED 733 total

includes taxes & fees

16 Nov - 17 Nov

A residential street with a white house, a paved driveway, and surrounding greenery.

3. Cozy 2-bedroom house in Park Hills

Park Hills

richard

A two-story house with a covered porch and a circular silo attached to the main building.

4. Silo Farm Haus- located in the heart of wine country!

Ste. Genevieve

Anthony S.

AED 1,360 total

includes taxes & fees

15 Nov - 16 Nov

An aerial view of a farm with barns, a winding road, and surrounding green fields.

5. Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

New Offenburg

Tamara M.

A kitchen with a white stove, black cabinets, a window with blue curtains, and a wooden floor.

6. Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations

Farmington

Amber P.

A backyard with a patio table and chairs, a barbecue grill, and a red building in the background.

7. Charming 1860s Renovated Home

Ironton

Kevin S.

AED 946 total

includes taxes & fees

13 Nov - 14 Nov

A swimming pool with a stone surround, a wooden pergola, and a stone pillar.

8. Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Park Hills

"We have a girls trip every year. This year we booked Linda’s house. It was awesome. There was plenty of rooms and space for all of us. The pool was amazing with the pavilion. We spent most of our time outside. We did a couple movie nights outside, some of us enjoyed the hot tub and we were in the pool every day. We did bring extra chairs, pool floaties and pool games. All in all we had a really good time full of memories"

Lisa C.

A pebbled riverbank with a forested hillside in the background.

9. Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Redford

zach f.

A wooden deck with Adirondack chairs and a bench, overlooking a grassy yard and trees.

10. Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Lesterville

St. Nicholas Children's T.

AED 1,772 total

includes taxes & fees

13 Nov - 14 Nov

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Top reviews in Madison County

A spacious kitchen with a dining area, featuring a ceiling fan, a TV mounted on the wall, and a large rug in the center.

Madison Inn Lodge

Fredericktown

10/10 Excellent

Anonymous traveler

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, a stove, and a granite countertop.

Shepherd Mountain Inn

Ironton

10/10 Excellent

We lived in Arcadia Valley 20 years ago. We revisited to show our grandson where his dad grew up. We were pleasantly surprised when we booked your motel. The renovations were nicely done. Your manager was very friendly and picked the perfect room for us as we returned daily from hiking and visiting old friends. The daily breakfast exceeded our expectations especially the warm food. Every area was clean and well kept by management and cleaning team. We recommend this motel to others when they...

Gwen