Madison County Holiday Rentals

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

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)
"We had a terrific, unplugged time visiting the farm and Shenandoah National Park. Thanks!"
United States
Maria N.
The price is NZ$187
includes taxes & fees
25 Nov - 26 Nov
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 NZ$341
includes taxes & fees
15 Nov - 16 Nov
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 NZ$426
includes taxes & fees
1 Dec - 2 Dec
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 NZ$486
includes taxes & fees
15 Nov - 16 Nov
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 NZ$465
includes taxes & fees
29 Nov - 30 Nov
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 NZ$839
includes taxes & fees
29 Nov - 30 Nov
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 NZ$1,085
includes taxes & fees
16 Nov - 17 Nov
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 NZ$820
includes taxes & fees
15 Nov - 16 Nov
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 NZ$1,128
includes taxes & fees
15 Nov - 16 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.

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 NZ$1,278
includes taxes & fees
16 Nov - 17 Nov
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 NZ$342
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A row of boats docked at a marina with a forested hill in the background.

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 NZ$228
includes taxes & fees
8 Dec - 9 Dec
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 NZ$232
includes taxes & fees
15 Nov - 16 Nov
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 NZ$373
includes taxes & fees
15 Nov - 16 Nov
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 NZ$230
includes taxes & fees
15 Dec - 16 Dec
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 NZ$439
includes taxes & fees
17 Nov - 18 Nov
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 NZ$338
includes taxes & fees
16 Nov - 17 Nov
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 NZ$306
includes taxes & fees
17 Nov - 18 Nov
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 NZ$282
includes taxes & fees
16 Nov - 17 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.

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 NZ$420
includes taxes & fees
15 Nov - 16 Nov
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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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

8/10 Good

a great place after a bit of juggling with the dog. It may be best to check with the place before as they had run out of pet friendly rooms which the site said they had but went out of their way to accommodate us. Had a lovely dinner outside with the dog attending as well.
Australia
Stephen
Reviewed May 30, 2020
Inn at Willow Grove

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 favorite 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 depends 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 selected for you start as low as NZ$186 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.