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Vacation rentals in Madison County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Madison County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Tiny living on The Hilltop
SUPERHOST
Tiny house · 2 guests · 1 bed · 1 bath

Tiny living on The HilltopTiny house living is about a minimalist lifestyle, leaving a smaller environmental footprint & greater financial freedom. Whether you’re interested in trying out Tiny Living or you just want to stay in a unique Airbnb, Hilltop Hideaway is for you! It’s a beautifully decorated, 208 sq ft Tiny house in the heart of historic Virginia.

The Sawmill Cottage-  Near Old Rag Mtn with views
SUPERHOST
Entire cottage · 4 guests · 2 beds · 1 bath

The Sawmill Cottage- Near Old Rag Mtn with viewsWe are located in the heart of Madison County on scenic route 231 near Old Rag Mountain and White Oak Canyon. This charming cottage sits on a half acre and is part of a 110 acre working farm. We have miles of walking paths or sit by the pond and enjoy a glass of wine or craft beer from one of our locals; Shotwell Run, DuCard or Revalation. Our little farm store offers Animal Welfare Approved meats, cheeses, eggs, seasonal fruits and veggies and locally made products.

Little House on Strother Run
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath

Little House on Strother RunNestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Vacation rentals for every style

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Popular amenities for Madison County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Madison County

SUPERHOST
  1. Private room
  2. Luray
The Loft at Peach Orchard Hideaway
SUPERHOST
  1. Entire cabin
  2. Madison
The Cabin at the Lake
SUPERHOST
  1. Entire guest suite
  2. Barboursville
Desired Haven - Barboursville, VA
SUPERHOST
  1. Tiny house
  2. Reva
K-9 Heaven -
SUPERHOST
  1. Entire bungalow
  2. Orange
Farm Cottage just outside town of Orange.
SUPERHOST
  1. Entire cottage
  2. Madison
Spectacular Mountain Retreat
SUPERHOST
  1. Farm stay
  2. Hood
Firnew Studio
SUPERHOST
  1. Entire cabin
  2. Etlan
Modern Cabin on Old Rag; Dog-Friendly
SUPERHOST
  1. Entire house
  2. Luray
Modern Farmhouse near Shenandoah Nat'l Park + Lake
SUPERHOST
  1. Farm stay
  2. Sperryville
The Roost at Upper Nonesuch
SUPERHOST
  1. Barn
  2. Madison
Three Brown Dog Barn, Three Brown Dog Farm, LLC
SUPERHOST
  1. Entire house
  2. Brightwood
Hilltop Haven Luxury lodging in Wine country