Madison County holiday rentals

We found 538 holiday rentals — enter your dates for availability
Discover a selection of 41 homes, 14 cabins and other holiday rentals in Madison County that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Popular Madison County destinations on Stayz

Holiday rentals with weekly discounts – Madison County

Showing deals for:13 Nov - 20 Nov

Living area
Property grounds
Living area
Dining
Exceptional
(12 reviews)

Rustic Farmhouse with Pool/hot tub/fire pits/6.5 acres Mountain Views

Luray

8% off
AU$6,529
for 7 nights, 1 room
AU$933 per night
includes taxes & fees
Rustic Farmhouse with Pool/hot tub/fire pits/6.5 acres Mountain Views
Private kitchen
S'mores anyone?
Living area
Interior
Exceptional
(27 reviews)

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

Sperryville

16% off
AU$4,036
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Living area
The pond and covered dock
New, Modern Eat-in Kitchen in both suites with stunning views
Living area
Exceptional
(117 reviews)

Serenity and adventure at historic Blue Ridge Farm

Sperryville

8% off
AU$5,569
for 7 nights, 1 home
AU$796 per night
includes taxes & fees
Serenity and adventure at historic Blue Ridge Farm
Interior
Exterior
Exterior
Property grounds
Exceptional
(133 reviews)

Enjoy a nature retreat in this secluded 4 bedroom lodge in Shenandoah,Virginia!

Shenandoah

7% off
AU$4,672
for 7 nights, 1 cabin
AU$667 per night
includes taxes & fees
Enjoy a nature retreat in this secluded 4 bedroom lodge in Shenandoah,Virginia!
Property grounds
Interior
Living area
Room
Exceptional
(6 reviews)

Escape the city at the Cross Mountain Hideaway. A spacious cabin by Luray.

Luray

19% off
AU$1,622
for 7 nights, 1 cabin
AU$232 per night
includes taxes & fees
Escape the city at the Cross Mountain Hideaway. A spacious cabin by Luray.
Interior
Living area
Bedroom 2, king bed
Catch your favorite streaming services on the 65” smart tv.
Exceptional
(24 reviews)

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Sperryville

16% off
AU$3,925
for 7 nights, 1 home
AU$561 per night
includes taxes & fees
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Property grounds
Terrace/patio
Interior
Living area
Exceptional
(61 reviews)

The Cabin at the Lake

Madison

8% off
AU$2,226
for 7 nights, 1 cabin
AU$318 per night
includes taxes & fees
The Cabin at the Lake
Exterior
Living area
Private kitchen
Interior
Exceptional
(9 reviews)

Modern A-Frame Cabin in the Heart of the Shenandoah Valley

Luray

11% off
AU$3,347
for 7 nights, 1 cabin
AU$478 per night
includes taxes & fees
Modern A-Frame Cabin in the Heart of the Shenandoah Valley
Recliners to enjoy the Fireplace, TV, and Mountain Views
Exterior
Great sunset viewing from the wrap-around deck
Gourmet Kitchen with textured granite countertops and stainless appliances
Exceptional
(13 reviews)

Stanley Hollow - 60 Acres, Starlink Satellite WiFi, 2 miles of private hiking

Stanley

8% off
AU$3,798
for 7 nights, 1 cabin
AU$543 per night
includes taxes & fees
Stanley Hollow - 60 Acres, Starlink Satellite WiFi, 2 miles of private hiking
Dining
Property grounds
Living area
Interior
Exceptional
(45 reviews)

Newly renovated entire guest suite in Orange County.

Orange

17% off
AU$1,163
for 7 nights, 1 home
AU$166 per night
includes taxes & fees
Newly renovated entire guest suite in Orange County.
Outdoor dining
Front
Interior
Private kitchen
Exceptional
(10 reviews)

Relaxing cottage in the woods just minutes from wineries,hiking,restaurants.

Barboursville

12% off
AU$2,390
for 7 nights, 1 cottage
AU$341 per night
includes taxes & fees
Relaxing cottage in the woods just minutes from wineries,hiking,restaurants.
Room
Living area
Interior
Dining
Exceptional
(105 reviews)

One of Central Virginia's most historic Private Guest Residences

Orange

6% off
AU$3,176
for 7 nights, 1 home
AU$454 per night
includes taxes & fees
One of Central Virginia's most historic Private Guest Residences
Living Room
Early Mountain Vineyards
Kitchen
Kitchen
Exceptional
(7 reviews)

Country Retreat Near Shenandoah & Old Rag | Family Friendly Getaway

Madison

6% off
AU$3,615
for 7 nights, 1 home
AU$516 per night
includes taxes & fees
Country Retreat Near Shenandoah & Old Rag | Family Friendly Getaway
View of deck and Blue Ridge from kitchen and great room
Barn in Snow
Great Room with a view!
Property grounds
Exceptional
(112 reviews)

Serenity and Adventure on Historic Blue Ridge Farm

Sperryville

8% off
AU$5,022
for 7 nights, 1 home
AU$717 per night
includes taxes & fees
Serenity and Adventure on Historic Blue Ridge Farm
Room
Exterior
Interior
Interior
Exceptional
(47 reviews)

The Historic Poorhouse at Cardinal Springs

Sperryville

8% off
AU$4,454
for 7 nights, 1 home
AU$636 per night
includes taxes & fees
The Historic Poorhouse at Cardinal Springs
Property grounds
Interior
Exterior detail
Private kitchen
Exceptional
(58 reviews)

South River Guest House

Stanardsville

8% off
AU$3,564
for 7 nights, 1 home
AU$509 per night
includes taxes & fees
South River Guest House
Pool
Pool with Winter cover; Farm Cottage and Aunt Judy's House beyond dependencies
Coming in the kitchen door
Terrace/patio
Exceptional
(72 reviews)

The PERFECT LOCATION FOR MAKING MEMORIES THAT WILL LAST A LIFETIME!!

Reva

8% off
AU$1,899
for 7 nights, 1 cottage
AU$271 per night
includes taxes & fees
The PERFECT LOCATION FOR MAKING MEMORIES THAT WILL LAST A LIFETIME!!
Living area
Property grounds
Room
Interior
Exceptional
(96 reviews)

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

Stanardsville

7% off
AU$1,748
for 7 nights, 1 home
AU$250 per night
includes taxes & fees
The House in the Holla at the foot of Shenandoah National Park
Interior
Relax
Room
Exterior
Exceptional
(15 reviews)

Charming 2-bedroom barn with WiFi, AC in brilliant Etlan, minutes from Old Rag.

Etlan

5% off
AU$1,965
for 7 nights, 1 home
AU$281 per night
includes taxes & fees
Charming 2-bedroom barn with WiFi, AC in brilliant Etlan, minutes from Old Rag.
Interior
You can count on homegrown, seasonal flower arrangements. We love our guests.
Modern stainless appliances are surrounded by Taj Mahal countertops
Rich character, high ceilings, original oak floors, wooden doors, glass knobs.
Exceptional
(33 reviews)

Classic Circa 1929 Estate by Montpelier, Wineries, Charlottesville, Pet Friendly

Somerset

8% off
AU$4,036
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Classic Circa 1929 Estate by Montpelier, Wineries, Charlottesville, Pet Friendly
Private kitchen
Living area
Room
Exterior
Exceptional
(22 reviews)

Shenandoah Valley Yurt

Stanley

8% off
AU$1,782
for 7 nights, 1 home
AU$255 per night
includes taxes & fees
Shenandoah Valley Yurt
Cottage: Firepit and Patio
Pool
The Front Door of the Cottage with the Blue Ridge Mtns in the distance.
February Sunset
Exceptional
(144 reviews)

Farm Living, Creature Comforts, & Centrally Located

Reva

8% off
AU$3,048
for 7 nights, 1 cottage
AU$435 per night
includes taxes & fees
Farm Living, Creature Comforts, & Centrally Located
Pano pic of front porch
Property grounds
Kitchen and top level seating area
Side view of Cabin
Exceptional
(105 reviews)

Cabin Fever in the foothills of the Blue Ridge Mountains

Luray

8% off
AU$2,419
for 7 nights, 1 cabin
AU$346 per night
includes taxes & fees
Cabin Fever in the foothills of the Blue Ridge Mountains
Dining
Terrace/patio
Private kitchen
Room
Exceptional
(9 reviews)

Families Paradise with walkable river access, playground, fire pit, BBQ, dogs OK

Shenandoah

11% off
AU$3,336
for 7 nights, 1 cabin
AU$477 per night
includes taxes & fees
Families Paradise with walkable river access, playground, fire pit, BBQ, dogs OK

Find the perfect holiday rental for your Madison County getaway

Learn about the unique charm of Madison County with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Madison County

Are you hoping to discover attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that Madison County has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Early Mountain Vineyards (3.5 mi / 5.6 km)
  • Barboursville Vineyards (15.3 mi / 24.6 km)
  • Keswick Vineyards and Winery (20.9 mi / 33.6 km)
  • Yogi Bear's Jellystone Park (21.5 mi / 34.5 km)
  • Little Washington Winery (21.6 mi / 34.8 km)
  • Shenandoah Speedway (22.4 mi / 36.1 km)

Exploring the natural features in Madison County

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Madison County is a great place to get outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah National Park (13.6 mi / 21.9 km)
  • Luray Caverns (23.1 mi / 37.2 km)
  • Old Rag Mountain (12.3 mi / 19.7 km)
  • Dark Hollow Falls (13.1 mi / 21.1 km)
  • Rose River Falls (13.3 mi / 21.3 km)
  • Swift Run Gap Entrance Shenandoah (15.7 mi / 25.2 km)

Frequently asked questions

What is the best area to stay in Madison County when booking a holiday home?
Among the more popular neighbourhoods to find a Madison County holiday home is Etlan. When you book a Stayz holiday home, you'll have the whole place to yourselves. So you won't have to share it with anybody except for your group.
What is the most popular type of holiday home accommodation in Madison County?
Houses are the most popular kind of holiday home in Madison County, according to our data. Even if you have something else in mind, Stayz has holiday homes in a variety of sizes and shapes. Browse our many options to find your perfect Madison County pad.
How much does it cost to rent a holiday home in Madison County?
Length of stay, property type and season are some factors that can determine the price of a holiday home. Simply add your travel dates to find your perfect escape. From cosy chalets to expansive villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Madison County?
When you travel and the style and size of the property will influence the cost of your beachside stay. Type in your Madison County travel dates to see all your options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to select the features and amenities you want in your home.
What are popular home amenities in Madison County?
Some of the most popular home amenities people look for in Madison County include a microwave oven, a fridge and an oven. Whether you're taking a trip with family, pals or even pets, Stayz holiday properties feature the best amenities for beginning new traditions with the people that matter most.
Are there large group holiday homes in Madison County?
With seven holiday homes that can host 10 guests or more in Madison County, you won't have to limit the invite list. From extended family holidays to events like anniversary parties and weddings, Stayz will help you find a large group home to match the occasion.
Can I find two-bedroom holiday homes in Madison County?
You can pick from 10 two-bedroom homes in Madison County. Put your little ones in the second room or fill it with a couple of your favourite people. There's plenty of space for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Madison County?
Madison County has 19 holiday homes with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to catching up on social media, these Stayz homes make it a breeze to get online.
How old do you have to be to rent a holiday home in Madison County?
It's a good idea to check with the Madison County holiday property you'd like on Stayz as age restrictions vary. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Madison County for?
The amount of time you can rent a Madison County holiday home for is down to each property. Simply enter your preferred travel dates to see options that offer extended stays. They include the things you need to make your extended getaway more enjoyable such as kitchens and air conditioning. Some Stayz holiday homes may also offer weekly or monthly discounts, so you can hang around longer for less.

More holiday ideas