Vacation Rentals in Madison County

Top cities in Madison County

A forest stream with rocks and fallen leaves.
Vacation Rentals

Syria

Syria

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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)
"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.
$93 nightly
The price is $104
Nov 17 - Nov 18
Total with taxes and fees
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
$231 nightly
The price is $240
Dec 1 - Dec 2
Total with taxes and fees
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.
$251 nightly
The price is $279
Nov 8 - Nov 9
Total with taxes and fees
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.
$247 nightly
The price is $275
Nov 29 - Nov 30
Total with taxes and fees
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.
$416 nightly
The price is $464
Nov 8 - Nov 9
Total with taxes and fees
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.
$540 nightly
The price is $601
Dec 3 - Dec 4
Total with taxes and fees
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.
$423 nightly
The price is $471
Nov 8 - Nov 9
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

8. 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.
$658 nightly
The price is $732
Nov 8 - Nov 9
Total with taxes and fees
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

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

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
$576 nightly
The price is $641
Nov 9 - Nov 10
Total with taxes and fees
Walk to Old Rag | Hot Tub | Mountain Farmhouse
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, (153 reviews)
"This is the perfect weekend getaway!!! Highly recommend staying here, so peaceful! The staff is amazing as well, very helpful and quick to respond."
United States
Caelin
$167 nightly
The price is $189
Dec 7 - Dec 8
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

11. 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
$163 nightly
The price is $185
Nov 9 - Nov 10
Total with taxes and fees
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A spacious living room with a large beige sectional sofa, two blue armchairs, a wooden coffee table, and a floor lamp.

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, (158 reviews)
"Excellent hotel. Very clean, comfortable, and great view of the water. Will definitely stay again"
United States
Josh
$125 nightly
The price is $140
Nov 8 - Nov 9
Total with taxes and fees
Boardwalk Hotel on Lake Anna by Kasa
A wooden cabin with a staircase leading to a covered porch, surrounded by a gravel area and a wooden fence.

13. 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.
$171 nightly
The price is $188
Nov 9 - Nov 10
Total with taxes and fees
Wood Haven Lodge 2 bedroom
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

14. 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.
$218 nightly
The price is $238
Nov 9 - Nov 10
Total with taxes and fees
Shenandoah Valley Yurt
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

15. 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
$124 nightly
The price is $139
Nov 9 - Nov 10
Total with taxes and fees
Roadhaven1830
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.
$145 nightly
The price is $156
Nov 9 - Nov 10
Total with taxes and fees
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.
$207 nightly
The price is $235
Nov 8 - Nov 9
Total with taxes and fees
The House in the Holla at the foot of Shenandoah National Park
A grassy field with a wooden fence, trees, and a distant building.

18. Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Gordonsville
9.8 out of 10, Exceptional, (143 reviews)
"The cottage had everything you need."
United States
William J.
$162 nightly
The price is $174
Nov 9 - Nov 10
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
A wooden deck with two sliding glass doors leading to a covered patio area.

19. 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.
$116 nightly
The price is $128
Nov 8 - Nov 9
Total with taxes and fees
Creekside Villa 1 bedroom
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 large, two-story building with a symmetrical facade, multiple windows, and a central entrance.
Inn at Willow Grove

Inn at Willow Grove

Inn at Willow Grove
Orange

10/10 Excellent

The suites( they are more than rooms) are marvelous. Quiet, great views and one of the most comfortable beds ever. The bathroom was also very nice, and the floor is heated. Couple that with butlered coffee and beignets each morning, and you’vr Got s high standard to beat
United States
Anonymous traveler
Reviewed December 30, 2018
Inn at Willow Grove

Frequently Asked Questions

How many vacation rentals are available in Madison County?

Expedia has plenty of vacation rentals to choose from in and around Madison County, so you’re guaranteed to find the right one for you.


How much is a vacation rental in Madison County?

The selection of Madison County vacation rentals we have selected for you start as low as $103 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Madison County?

Vacation rentals in Madison County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Madison County vacation rentals to suit everyone.


Why should I choose a vacation rental in Madison County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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.


How do I find the best deal on a vacation rental in Madison County?

Find vacation rentals in Madison County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Madison County.


What amenities are available in a vacation rental in Madison County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Madison County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Madison County?

Everytime is a great time to head to Madison County! Staying in a Madison County vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Madison County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Madison County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Madison County, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Madison County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.


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