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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Madison vacation 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 ￥21,253
￥38,854 total
includes taxes & fees
Oct 4 - Oct 5
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 ￥34,477
￥69,038 total
includes taxes & fees
Oct 4 - Oct 5
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 ￥36,996
￥72,191 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥19,671
￥31,006 total
includes taxes & fees
Oct 7 - Oct 8
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, (30 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 ￥19,679
￥35,318 total
includes taxes & fees
Oct 5 - Oct 6
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A tent set up in a forested area with a checkered mat inside.

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 ￥17,711
￥27,598 total
includes taxes & fees
Oct 7 - Oct 8
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

7. 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 ￥18,490
￥38,855 total
includes taxes & fees
Oct 8 - Oct 9
The House in the Holla at the foot of Shenandoah National Park
A house with a brick chimney, a small window, and a wooden deck.

8. 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 ￥17,002
￥25,845 total
includes taxes & fees
Oct 12 - Oct 13
Newly renovated entire guest suite in Orange County.
A single-story house with a front porch, a chimney, and a small garden area.

9. 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 traveler
The price is ￥17,632
￥40,669 total
includes taxes & fees
Oct 5 - Oct 6
Quiet-peaceful 2-bedroom house with AC in Stanardsville, VA. No pets.
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 ￥19,836
￥34,247 total
includes taxes & fees
Oct 8 - Oct 9
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 ￥30,699
￥45,149 total
includes taxes & fees
Oct 4 - Oct 5
The Pembroke Room in the historic Holladay House
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

12. 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 ￥25,189
￥30,575 total
includes taxes & fees
Oct 5 - Oct 6
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

13. 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 ￥33,722
￥74,238 total
includes taxes & fees
Oct 4 - Oct 5
Charming 3-bdrm house in Ruckersville offering great location for your vacation
A kitchen with white cabinets, a granite countertop, and a tiled floor.

14. 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 ￥12,988
￥32,898 total
includes taxes & fees
Oct 5 - Oct 6
Red Brush Cottage Property
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 ￥20,781
￥44,051 total
includes taxes & fees
Oct 5 - Oct 6
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, (12 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is ￥14,027
￥35,823 total
includes taxes & fees
Oct 4 - Oct 5
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.

17. “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)
"Tracy was very welcoming and friendly. The accommodation was great."
United States
Linda N.
The price is ￥35,280
￥50,355 total
includes taxes & fees
Oct 6 - Oct 7
“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.

18. 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 ￥32,163
￥57,147 total
includes taxes & fees
Oct 12 - Oct 13
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
A living room with a dark-colored sofa, a glass coffee table, a floor lamp, and a TV mounted on the wall.

19. 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 ￥34,635
￥41,893 total
includes taxes & fees
Oct 5 - Oct 6
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Outdoor spa tub

20. Family Getaway at Cross Mountain

Family Getaway at Cross Mountain
Luray
10.0 out of 10, Exceptional, (23 reviews)
"House is beautiful and owner was very responsive !I will be booking again in the future ! "
United States
Edgar P.
The price is ￥23,473
￥59,937 total
includes taxes & fees
Oct 5 - Oct 6
Family Getaway at Cross Mountain
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

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

10/10 Excellent
"Clean modern rooms. Professional staff. Good breakfast"
Stephen 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Find out more about Madison

Madison Vacation Homes information

Number of reviews
414
Accommodation
701 Vacation Homes
Lowest Price
￥25,845
Highest Price
￥74,238