A large pink building with a blue roof, surrounded by a well-maintained lawn and dense trees.

Holiday Homes in Madison

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Madison holiday homes

A hallway with a wooden bench, a red door, and a framed picture on the wall.

1. Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
United States
Tracy
The price is €231
includes taxes & fees
2 Nov - 3 Nov
Historic Madison Eagle Inn
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

2. Charming 4-bedroom house in Madison centrally located!

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (4 reviews)
"The home met all our family’s needs during a weekend stay for a party at nearby farm. The layout and outdoor spaces were a bonus. In fact, the view of Hawksbill Mountain from the porch while enjoying our morning coffee: priceless. And importantly easy access to Rt 29 and the town but yet secluded and bucolic."
United States
B D.
The price is €402
includes taxes & fees
28 Oct - 29 Oct
Charming 4-bedroom house in Madison centrally located!
A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

3. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
8.0 out of 10, Very good, (1 review)
"Positive Highlights: quiet location still close to Skyline Drive, amenities, fresh interior recently modernized, love for details (charging cables, coffee bar, etc)"
United States
Birgit W.
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A modern kitchen with a central island, bar stools, and pendant lighting.

4. Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Etlan
10.0 out of 10, Exceptional, (35 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is €171
includes taxes & fees
28 Oct - 29 Oct
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

5. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (35 reviews)
"Stayed here for a weekend while hiking Old Rag in Shenandoah. Cozy little place that was well equipped with all the amenities we needed! It's conveniently located close to Shenandoah as well as plenty of vineyards. Would not hesitate to stay here again the next time we're in the area!"
United States
Jason
The price is €207
includes taxes & fees
28 Oct - 29 Oct
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A wooden gazebo with a sloped roof, surrounded by lush greenery and purple flowers.

6. Butterfly Camp near Old Rag Mountain and Shenandoah National Park

Butterfly Camp near Old Rag Mountain and Shenandoah National Park
Etlan
The price is €173
includes taxes & fees
19 Nov - 20 Nov
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A house with a brick chimney, a small window, and a wooden deck.

7. Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (45 reviews)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
United States
vishal k.
The price is €151
includes taxes & fees
28 Oct - 29 Oct
Newly renovated entire guest suite in Orange County.
A living room with a fireplace, a chandelier, and a sofa.

8. The Pembroke Room in the historic Holladay House

The Pembroke Room in the historic Holladay House
Orange
9.4 out of 10, Exceptional, (3 reviews)
"The property is in the perfect location for a visit to Montpelier! Great restaurants and events are nearby. Very cozy! Great host! Expect what you would expect from a historic home. We will return."
United States
Robert
The price is €263
includes taxes & fees
9 Nov - 10 Nov
The Pembroke Room in the historic Holladay House
A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

9. Charming 3-bdrm house in Ruckersville offering great location for your vacation

Charming 3-bdrm house in Ruckersville offering great location for your vacation
Ruckersville
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, we enjoyed our stay. "
United States
Carol T.
The price is €424
includes taxes & fees
28 Oct - 29 Oct
Charming 3-bdrm house in Ruckersville offering great location for your vacation
A porch with a wooden bench, metal railing, and potted plants.

10. Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. No pets.

Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. No pets.
Stanardsville
10.0 out of 10, Exceptional, (6 reviews)
"We stay in rentals quite often in this area. This is one of the best ones for the price. This house was conveniently located to everything but far enough away for the peace and quiet. The house was well equipped for those of us who like to cook. We really enjoyed our stay and plan on returning if available going forward."
United States
Anonymous traveller
Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. No pets.
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

11. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville
9.6 out of 10, Exceptional, (47 reviews)
"Beautiful property and family friendly."
United States
Tracy
The price is €161
includes taxes & fees
28 Oct - 29 Oct
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A kitchen with white cabinets, a granite countertop, and a tiled floor.

12. Red Brush Cottage Property

Red Brush Cottage Property
Elkton
9.0 out of 10, Wonderful, (2 reviews)
"Basic, updated cottage that met our needs for an overnight with family. Sparsely furnished but worked for us. Thanks."
United States
Margaret
The price is €223
includes taxes & fees
8 Nov - 9 Nov
Red Brush Cottage Property
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a herringbone wood floor.

13. RiverFront Country Home with Blue Mountain Views

RiverFront Country Home with Blue Mountain Views
Free Union
9.8 out of 10, Exceptional, (42 reviews)
"Enjoyed our stay."
United States
Katrecia B.
The price is €180
includes taxes & fees
9 Nov - 10 Nov
RiverFront Country Home with Blue Mountain Views
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

14. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (31 reviews)
"Wonderful, communicative host in a beautiful, quiet area. Would definitely come back again!"
United States
MiaMaria C.
The price is €256
includes taxes & fees
4 Nov - 5 Nov
Shenandoah Valley Yurt
A small, single-story wooden cabin with a white-framed door and a small porch.

15. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.8 out of 10, Exceptional, (17 reviews)
"Very comfortable and clean space. Plenty of room for 1 or 2 people. Check in and out instructions were very detailed. Price was very affordable compared to the nicer hotels in town who were charging $200 to $300 a night. Kind of out in the country but its easy to get to and from town, pretty straight stretch. I was only there in the evenings and everything was very quiet and peaceful."
United States
emily
The price is €209
includes taxes & fees
28 Oct - 29 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
An outdoor patio area with two wicker chairs and a small table, surrounded by a stone wall and a white fence.

16. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville
10.0 out of 10, Exceptional, (38 reviews)
"Absolutely lovely place to stay. Stunning views and conveniently located to so many of the local attractions. Will definitely come back someday."
United States
Kirby R.
The price is €293
includes taxes & fees
28 Oct - 29 Oct
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
A living room with a dark-colored sofa, a glass coffee table, a floor lamp, and a TV mounted on the wall.

17. Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful place"
United States
Berhan S.
The price is €215
includes taxes & fees
1 Nov - 2 Nov
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
A wicker basket with brochures on a glass table, a white vase with white flowers, and a white chair in a room with a window.

18. Charming 3-Bed Cottage on Main Street in Historic Gordonsville

Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Gordonsville
9.8 out of 10, Exceptional, (21 reviews)
"This was the cutest house! Our favorite of our weeklong roadtrip. Perfect for our 6 adults. Close to town, which was adorable also. Would love to come back and stay again!"
United States
Cheryl G.
The price is €323
includes taxes & fees
28 Oct - 29 Oct
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

19. Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Etlan
9.4 out of 10, Exceptional, (73 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is €670
includes taxes & fees
28 Oct - 29 Oct
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
S'mores anyone?

20. Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Sperryville
10.0 out of 10, Exceptional, (32 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is €694
includes taxes & fees
9 Nov - 10 Nov
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews

Massanutten Resort

Massanutten Resort

8/10 Good
"We stayed in a hotel room that was several miles removed from the resort lodge. The room and surroundings were very nice for our one night stay"
Glenn 1-night trip
Posted 2 hours ago
Massanutten Resort

Find out more about Madison

Madison Holiday Homes information

Number of reviews
386
Accommodation
716 Holiday Homes
Lowest Price
€151
Highest Price
€694