A mountainous landscape with large boulders and distant hills.

Madison County Holiday Rentals

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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, (21 reviews)
"Great host. Super clean. Excellent driving directions and walking info to get to the cabin. Awesome solution for people who love camping"
United States
Patrick
The price is AU$161
includes taxes & fees
23 Sept - 24 Sept
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A modern kitchen with a central island, bar stools, and pendant lighting.

2. 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, (28 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is AU$255
includes taxes & fees
23 Sept - 24 Sept
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

3. 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$345
includes taxes & fees
4 Oct - 5 Oct
Historic Madison Eagle Inn
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

4. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (62 reviews)
"Great view and access to the lake!"
United States
Leti H.
The price is AU$411
includes taxes & fees
23 Sept - 24 Sept
The Cabin at the Lake
A rustic outdoor seating area with a table and chairs surrounded by a forest.

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

Butterfly Camp near Old Rag Mountain and Shenandoah National Park
Etlan
The price is AU$249
includes taxes & fees
23 Sept - 24 Sept
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

6. 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 AU$605
includes taxes & fees
23 Sept - 24 Sept
Charming 4-bedroom house in Madison centrally located!

7. 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, (28 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is AU$786
includes taxes & fees
23 Sept - 24 Sept
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
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, (26 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is AU$835
includes taxes & fees
24 Sept - 25 Sept
Walk to Old Rag | Hot Tub | Mountain 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.

9. 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$634
includes taxes & fees
23 Sept - 24 Sept
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A wooden interior with a table, chair, and a hanging lantern.

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, (141 reviews)
"Fantastic stay!! Everything was perfect."
United States
Humberto
The price is AU$269
includes taxes & fees
23 Sept - 24 Sept
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
9.0 out of 10, Wonderful, (141 reviews)
"A very nice place. Very clean and comfortable. Would definitely stay again."
United States
Stephanie
The price is AU$185
includes taxes & fees
30 Sept - 1 Oct
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, (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 AU$318
includes taxes & fees
12 Oct - 13 Oct
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A small, single-story wooden cabin with a white-framed door and a small porch.

13. 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, (11 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is AU$317
includes taxes & fees
3 Oct - 4 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

14. 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, (97 reviews)
"The house is very clean and supplied with everything you will need."
United States
Mike I.
The price is AU$351
includes taxes & fees
23 Sept - 24 Sept
The House in the Holla at the foot of Shenandoah National Park

15. Charming Cottage w/ Incredible Views & Firepit

Charming Cottage w/ Incredible Views & Firepit
Stanley
10.0 out of 10, Exceptional, (25 reviews)
"Nice quaint house in the country"
United States
Adam R.
The price is AU$511
includes taxes & fees
23 Sept - 24 Sept
Charming Cottage w/ Incredible Views & Firepit
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

16. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (51 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is AU$209
includes taxes & fees
12 Oct - 13 Oct
Roadhaven1830
A wooden deck with two sliding glass doors leading to a covered patio area.

17. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Clean room and great space."
United States
Makenzi
The price is AU$195
includes taxes & fees
19 Oct - 20 Oct
Creekside Villa 1 bedroom
A wooden cabin with a staircase leading to a covered porch, surrounded by a gravel area and a wooden fence.

18. Wood Haven Lodge 2 bedroom

Wood Haven Lodge 2 bedroom
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Had a great stay. Property was clean and cozy. Beautiful views. Loved the farm setting! "
United States
Timea Z.
The price is AU$302
includes taxes & fees
30 Sept - 1 Oct
Wood Haven Lodge 2 bedroom
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

19. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (29 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 AU$384
includes taxes & fees
23 Sept - 24 Sept
Shenandoah Valley Yurt
A modern house with a deck, surrounded by a well-maintained lawn and trees.

20. Whispering Hillside -Coffee Bar, Hot Tub Fire Pit

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (60 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is AU$486
includes taxes & fees
24 Sept - 25 Sept
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
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 County Hotel Reviews

Omni Charlottesville Hotel

Omni Charlottesville Hotel

10/10 Excellent
"We had a wonderful stay! The staff was friendly and extremely helpful. Our room was spotless, and provided a lovely retreat prior to our event at the Ting Pavillion. The hotel's location right on the mall made everything so much easier. I will definitely book again."
Dagmar 1-night trip
Posted 1 hour ago
Omni Charlottesville Hotel

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$161 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.