A mountainous landscape with large boulders and distant hills.

Madison County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Madison County holiday rentals

A cabin with a wooden deck, two chairs, a red door, and a window.

1. Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (25 reviews)
"Hose was excellent, great communication, helpful, answered questions, even returned items inadvertently left behind. Location was great for activities around the national park and caverns."
United States
Tracy P.
The price is AU$151
includes taxes & fees
17 Nov - 18 Nov
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A hallway with a wooden bench, a red door, and a framed picture on the wall.

2. 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 AU$349
includes taxes & fees
1 Dec - 2 Dec
Historic Madison Eagle Inn
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

3. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (68 reviews)
"Perfect little getaway."
United States
Vernon M.
The price is AU$400
includes taxes & fees
8 Nov - 9 Nov
The Cabin at the Lake
A wooden cabin with a porch, stone pathway, and outdoor seating.

4. Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A

Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
Madison
10.0 out of 10, Exceptional, (11 reviews)
"This house was perfect for our weekend stay. It was very clean and had a well stocked kitchen and bathrooms. There was plenty of space for our family of 5 to spread out and relax. The beds were all comfortable to sleep in too."
United States
Megan F.
The price is AU$399
includes taxes & fees
29 Nov - 30 Nov
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

5. 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 AU$659
includes taxes & fees
8 Nov - 9 Nov
Charming 4-bedroom house in Madison centrally located!
S'mores anyone?

6. 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, (33 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is AU$855
includes taxes & fees
3 Dec - 4 Dec
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

7. 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 AU$672
includes taxes & fees
8 Nov - 9 Nov
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

8. Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
The price is AU$930
includes taxes & fees
9 Nov - 10 Nov
Walk to Old Rag | Hot Tub | Mountain Farmhouse
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

9. 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, (74 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is AU$1,056
includes taxes & fees
8 Nov - 9 Nov
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A glass enclosure with a view of a forest interior, including a bed and various plants.

10. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.4 out of 10, Exceptional, (154 reviews)
"Picture perfect, seemless check in and the coffee and maple oatmeal were my cherry on top!"
United States
Rachel
The price is AU$273
includes taxes & fees
7 Dec - 8 Dec
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A spacious living room with a large beige sectional sofa, two blue armchairs, a wooden coffee table, and a floor lamp.

11. Boardwalk Hotel on Lake Anna by Kasa

Boardwalk Hotel on Lake Anna by Kasa
4.0 star property
Louisa
9.2 out of 10, Wonderful, (158 reviews)
"Excellent hotel. Very clean, comfortable, and great view of the water. Will definitely stay again"
United States
Josh
The price is AU$182
includes taxes & fees
8 Nov - 9 Nov
Boardwalk Hotel on Lake Anna by Kasa
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

12. 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 AU$268
includes taxes & fees
16 Nov - 17 Nov
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A kitchen with wooden cabinets, a granite countertop, a sink, a toaster, and a window with a view of a rocky landscape.

13. Cascina Rococo at White Lotus Eco Spa Retreat

Cascina Rococo at White Lotus Eco Spa Retreat
Stanardsville
9.2 out of 10, Wonderful, (16 reviews)
"The room was very clean and welcoming. "
United States
Maria
The price is AU$246
includes taxes & fees
9 Nov - 10 Nov
Cascina Rococo at White Lotus Eco Spa Retreat
A wooden cabin with a staircase leading to a covered porch, surrounded by a gravel area and a wooden fence.

14. Wood Haven Lodge 2 bedroom

Wood Haven Lodge 2 bedroom
Elkton
10.0 out of 10, Exceptional, (14 reviews)
"Great location smooth transaction"
United States
Evan S.
The price is AU$275
includes taxes & fees
9 Nov - 10 Nov
Wood Haven Lodge 2 bedroom
A wooden deck with two sliding glass doors leading to a covered patio area.

15. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (16 reviews)
"Cozy cabin, perfect for a solo retreat to rest and relax."
United States
Rachael C.
The price is AU$186
includes taxes & fees
8 Nov - 9 Nov
Creekside Villa 1 bedroom
A house with a brick chimney, a small window, and a wooden deck.

16. 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 AU$226
includes taxes & fees
9 Nov - 10 Nov
Newly renovated entire guest suite in Orange County.
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

17. 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, (102 reviews)
"Very peaceful and quiet, but relatively close to Charlottesville."
United States
Victor V.
The price is AU$341
includes taxes & fees
8 Nov - 9 Nov
The House in the Holla at the foot of Shenandoah National Park
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

18. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (32 reviews)
"Wonderful, communicative host in a beautiful, quiet area. Would definitely come back again!"
United States
MiaMaria C.
The price is AU$345
includes taxes & fees
9 Nov - 10 Nov
Shenandoah Valley Yurt
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

19. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (54 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is AU$188
includes taxes & fees
8 Dec - 9 Dec
Roadhaven1830
A forested area with a fire pit and Adirondack chairs.

20. Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
9.8 out of 10, Exceptional, (42 reviews)
"It was a very pleasant stay. We chatted it up with Stuart the owner he was very nice. The place was super clean and we had everything we needed. We would totally stay again. Great experience!"
United States
Matt
The price is AU$296
includes taxes & fees
8 Nov - 9 Nov
Moonfire Farm Shenandoah region cozy getaway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison County Hotel Reviews

Quality Inn Luray

Quality Inn Luray

8/10 Good
"Busy restaurant with friendly staff"
Stephen 1-night trip
Posted 3 hours ago
Quality Inn Luray

Find out more about Madison County

Everything you need to know about Madison County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madison County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Madison County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Madison County holiday rentals we have chosen for you start as low as AU$151 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Madison County rentals

At Expedia, we put the best Madison County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Madison County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.