Madison County Vacation Rentals

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Top cities in Madison County

A forest stream with rocks and fallen leaves.
Vacation Rentals

Syria

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Madison County vacation 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)
"We had a terrific, unplugged time visiting the farm and Shenandoah National Park. Thanks!"
United States
Maria N.
The price is CA $116
CA $148 total
includes taxes & fees
Nov 17 - Nov 18
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A rustic wooden fence with a metal gate, surrounded by autumn foliage and a small pumpkin decoration.

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, (37 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is CA $212
CA $295 total
includes taxes & fees
Nov 20 - Nov 21
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A large, stone building with a dark roof, surrounded by well-maintained gardens and a mountainous backdrop.

3. Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
United States
Tracy
The price is CA $198
CA $345 total
includes taxes & fees
Dec 1 - Dec 2
Historic Madison Eagle Inn
A wooden dock extending into a calm lake surrounded by dense green trees.

4. 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 CA $225
CA $401 total
includes taxes & fees
Nov 17 - Nov 18
The Cabin at the Lake
A wooden cabin with a porch, stone pathway, and outdoor seating.

5. 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, (12 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 CA $184
CA $376 total
includes taxes & fees
Nov 29 - Nov 30
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
A two-story white house with a grey roof, a front porch, and a basketball hoop.

6. 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 CA $366
CA $666 total
includes taxes & fees
Nov 29 - Nov 30
Charming 4-bedroom house in Madison centrally located!
S'mores anyone?

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, (34 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is CA $364
CA $861 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A spacious kitchen with a central island, bar stools, and a dining area with a table and chairs.

8. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
9.0 out of 10, Wonderful, (2 reviews)
"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 CA $376
CA $679 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A group of white Adirondack chairs arranged around a fire pit in a grassy outdoor area with trees in the background.

9. 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 CA $409
CA $915 total
includes taxes & fees
Nov 16 - Nov 17
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.

10. 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 CA $636
CA $1,044 total
includes taxes & fees
Nov 16 - Nov 17
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

11. 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, (156 reviews)
"Picture perfect, seemless check in and the coffee and maple oatmeal were my cherry on top!"
United States
Rachel
The price is CA $181
CA $270 total
includes taxes & fees
Dec 14 - Dec 15
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A multi-story residential building with balconies, a covered front porch, and a driveway.

12. 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, (159 reviews)
"Excellent hotel. Very clean, comfortable, and great view of the water. Will definitely stay again"
United States
Josh
The price is CA $161
CA $180 total
includes taxes & fees
Dec 2 - Dec 3
Boardwalk Hotel on Lake Anna by Kasa
A covered deck with two lounge chairs and a view of a gravel path leading to a grassy area with trees.

13. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (17 reviews)
"Cozy cabin, perfect for a solo retreat to rest and relax."
United States
Rachael C.
The price is CA $63
CA $183 total
includes taxes & fees
Nov 23 - Nov 24
Creekside Villa 1 bedroom
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

14. 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, (36 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 CA $207
CA $297 total
includes taxes & fees
Nov 16 - Nov 17
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A backyard with a pergola, string lights, and a swing set.

15. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.4 out of 10, Exceptional, (55 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is CA $173
CA $195 total
includes taxes & fees
Dec 16 - Dec 17
Roadhaven1830
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

16. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (33 reviews)
"Wonderful, communicative host in a beautiful, quiet area. Would definitely come back again!"
United States
MiaMaria C.
The price is CA $158
CA $349 total
includes taxes & fees
Nov 17 - Nov 18
Shenandoah Valley Yurt
A wooden deck with a bench and a hanging light fixture.

17. Wood Haven Lodge 2 bedroom

Wood Haven Lodge 2 bedroom
Elkton
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful property and peaceful stay"
United States
Daphne G.
The price is CA $118
CA $268 total
includes taxes & fees
Nov 16 - Nov 17
Wood Haven Lodge 2 bedroom
A wooden deck with a covered pavilion, wooden railings, and a view of trees and water.

18. Glade Cottage at White Lotus Eco Spa Retreat

Glade Cottage at White Lotus Eco Spa Retreat
Stanardsville
8.6 out of 10, Excellent, (26 reviews)
"Great stay"
United States
Caroline T.
The price is CA $151
CA $243 total
includes taxes & fees
Nov 17 - Nov 18
Glade Cottage at White Lotus Eco Spa Retreat
A brick planter box with various potted plants and flowers.

19. Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (46 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 CA $154
CA $222 total
includes taxes & fees
Nov 16 - Nov 17
Newly renovated entire guest suite in Orange County.
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

20. 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, (104 reviews)
"Very peaceful and quiet, but relatively close to Charlottesville."
United States
Victor V.
The price is CA $167
CA $336 total
includes taxes & fees
Nov 16 - Nov 17
The House in the Holla at the foot of Shenandoah National Park
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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Find vacation rentals that suit your style

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Top Madison County Hotel Reviews

A view of a green field and a tree with white flowers, with a metal roof in the foreground.
Round Hill Inn

Round Hill Inn

Round Hill Inn
Orange

10/10 Excellent

Great location for what we needed. Clean and the staff were very friendly
Canada
Sarah
Reviewed September 17, 2025
Round Hill Inn

Find out more about Madison County

Everything you need to know about Madison County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison County vacation rentals we have selected for you start as low as CA $115 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 vacation 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 vacation.

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.