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Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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

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.

Hebron Valley Cottage
SUPERHOST
Entire guesthouse · 4 guests · 2 beds · 1 bath

Hebron Valley CottageNestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.

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.

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Popular amenities for Madison vacation rentals

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

Other great vacation rentals in Madison

SUPERHOST
  1. Private room
  2. Luray
The Loft at Peach Orchard Hideaway
SUPERHOST
  1. Tiny house
  2. Brightwood
Tiny living on The Hilltop
SUPERHOST
  1. Entire guest suite
  2. Barboursville
Desired Haven - Barboursville, VA
SUPERHOST
  1. Entire cabin
  2. Madison
The Cabin at the Lake
SUPERHOST
  1. Entire bungalow
  2. Orange
Farm Cottage just outside town of Orange.
SUPERHOST
  1. Entire house
  2. Radiant
TuckerBerry Farm - 2 rooms in the farmhouse
SUPERHOST
  1. Entire cottage
  2. Madison
THE PERFECT HIKING & WINERY COUNTRY RETREAT
SUPERHOST
  1. Entire guesthouse
  2. Earlysville
Cottage at Frog Jump- woodland privacy at its best
SUPERHOST
  1. Entire cabin
  2. Etlan
Modern Cabin on Old Rag; Dog-Friendly
SUPERHOST
  1. Private room
  2. Stanardsville
Elbow Room at The White Lotus Eco Spa Retreat
SUPERHOST
  1. Entire cabin
  2. Gordonsville
Gum Tree Lodge
SUPERHOST
  1. Entire house
  2. Brightwood
Hilltop Haven Luxury lodging in Wine country

Nearby destinations