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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Madison holiday homes

A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

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 NZ$441
includes taxes & fees
6 Oct - 7 Oct
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, (3 reviews)
"Our stay was excellent. The host was responsive to every need. The house was beautiful. The view from the front window is beautiful!! The bathtub and shower in the main bathroom is luxurious!! We would be willing to stay there again."
United States
Lori K.
The price is NZ$829
includes taxes & fees
7 Oct - 8 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.
The price is NZ$844
includes taxes & fees
6 Oct - 7 Oct
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, (31 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is NZ$349
includes taxes & fees
6 Oct - 7 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, (31 reviews)
"The property is perfect for a weekend getaway for a couple of a small family with kids. I really enjoyed my stay and would recommend it."
United States
Ronald
The price is NZ$402
includes taxes & fees
6 Oct - 7 Oct
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

6. The House in the Holla at the foot of Shenandoah National Park

The House in the Holla at the foot of Shenandoah National Park
Stanardsville
9.8 out of 10, Exceptional, (98 reviews)
"The house is very clean and supplied with everything you will need."
United States
Mike I.
The price is NZ$436
includes taxes & fees
8 Oct - 9 Oct
The House in the Holla at the foot of Shenandoah National Park
A directional sign for the Farm Store Trail in a forested area.

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

Butterfly Camp near Old Rag Mountain and Shenandoah National Park
Etlan
The price is NZ$312
includes taxes & fees
7 Oct - 8 Oct
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A single-story house with a front porch, a chimney, and a small garden area.

8. 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, (5 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
The price is NZ$462
includes taxes & fees
6 Oct - 7 Oct
Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. No pets.
A house with a brick chimney, a small window, and a wooden deck.

9. 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 NZ$315
includes taxes & fees
19 Oct - 20 Oct
Newly renovated entire guest suite in Orange County.
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a herringbone wood floor.

10. RiverFront Country Home with Blue Mountain Views

RiverFront Country Home with Blue Mountain Views
Free Union
9.8 out of 10, Exceptional, (40 reviews)
"Enjoyed our stay."
United States
Katrecia B.
The price is NZ$313
includes taxes & fees
7 Oct - 8 Oct
RiverFront Country Home with Blue Mountain Views
A living room with a fireplace, a chandelier, and a sofa.

11. 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 NZ$507
includes taxes & fees
6 Oct - 7 Oct
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.

12. 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
10.0 out of 10, Exceptional, (16 reviews)
"Nice home, we enjoyed our stay. "
United States
Carol T.
The price is NZ$838
includes taxes & fees
6 Oct - 7 Oct
Charming 3-bdrm house in Ruckersville offering great location for your vacation
A kitchen with white cabinets, a granite countertop, and a tiled floor.

13. 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 NZ$378
includes taxes & fees
6 Oct - 7 Oct
Red Brush Cottage Property
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

14. 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
9.8 out of 10, Exceptional, (46 reviews)
"Beautiful property and family friendly."
United States
Tracy
The price is NZ$344
includes taxes & fees
6 Oct - 7 Oct
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

15. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (30 reviews)
"Great place to stay with a very responsive and flexible host! Check in and check out was very easy"
United States
Ron G.
The price is NZ$459
includes taxes & fees
3 Nov - 4 Nov
Shenandoah Valley Yurt
A small, single-story wooden cabin with a white-framed door and a small porch.

16. 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, (13 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is NZ$403
includes taxes & fees
8 Oct - 9 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A fire pit with a visible brand name, surrounded by outdoor furniture and a scenic view of mountains.

17. Shenandoah Hideaway

Shenandoah Hideaway
Page County
10.0 out of 10, Exceptional, (19 reviews)
"Great quiet location with great view from the back yard. Plenty of amenities to make our stay comfortable. "
United States
SCOTT B.
The price is NZ$817
includes taxes & fees
15 Oct - 16 Oct
Shenandoah Hideaway
An outdoor patio area with two wicker chairs and a small table, surrounded by a stone wall and a white fence.

18. “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 NZ$560
includes taxes & fees
6 Oct - 7 Oct
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
A two-story house with a porch, a front door, and a small garden with a pumpkin.

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

Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Gordonsville
10.0 out of 10, Exceptional, (18 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 NZ$696
includes taxes & fees
19 Oct - 20 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.

20. 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 NZ$1,287
includes taxes & fees
6 Oct - 7 Oct
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
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

10/10 Excellent
"The condo was very clean and spacious."
Elissa 2-night trip
Posted 4 hours ago
Massanutten Resort

Find out more about Madison

Madison Holiday Homes information

Number of reviews
427
Accommodation
709 Holiday Homes
Lowest Price
NZ$312
Highest Price
NZ$1,287

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