A large pink building with a blue roof, surrounded by a well-maintained lawn and dense trees.

Madison Vacation Rentals

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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 vacation rentals

A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

1. 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
Nov 5 - Nov 6
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.

2. 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 5 - Nov 6
Total with taxes and fees
The Cabin at the Lake
A wooden cabin with a porch, stone pathway, and outdoor seating.

3. 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.

4. 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 5 - Nov 6
Total with taxes and fees
Charming 4-bedroom house in Madison centrally located!
A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

5. 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 cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

6. 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
$199 nightly
The price is $225
Dec 1 - Dec 2
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A cabin with a wooden deck, two chairs, a red door, and a window.

7. 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 15 - Nov 16
Total with taxes and fees
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A two-story house with a stone facade, a front porch, and a well-maintained lawn.

8. 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
$156 nightly
The price is $177
Nov 5 - Nov 6
Total with taxes and fees
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

9. 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.
$199 nightly
The price is $225
Nov 5 - Nov 6
Total with taxes and fees
The House in the Holla at the foot of Shenandoah National Park
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a herringbone wood floor.

10. RiverFront Country Home with Blue Mountain Views

RiverFront Country Home with Blue Mountain Views
Free Union
9.8 out of 10, Exceptional, (42 reviews)
"Enjoyed our stay."
United States
Katrecia B.
$164 nightly
The price is $186
Nov 17 - Nov 18
Total with taxes and fees
RiverFront Country Home with Blue Mountain Views
A house with a brick chimney, a small window, and a wooden deck.

11. 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 kitchen with white cabinets, a granite countertop, and a tiled floor.

12. Red Brush Cottage Property

Red Brush Cottage Property
Elkton
9.0 out of 10, Wonderful, (2 reviews)
"Basic, updated cottage that met our needs for an overnight with family. Sparsely furnished but worked for us. Thanks."
United States
Margaret
$197 nightly
The price is $198
Nov 9 - Nov 10
Total with taxes and fees
Red Brush Cottage Property
Outdoor dining

13. 10 mins from Shenandoah National Park ~ Cozy Cabin

10 mins from Shenandoah National Park ~ Cozy Cabin
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay there, it was only a night but the cottage has everything you need for a relaxing trip. The hot tub was super easy to use and the view of the woods was beautiful."
United States
Tamsin D.
$244 nightly
The price is $269
Nov 17 - Nov 18
Total with taxes and fees
10 mins from Shenandoah National Park ~ Cozy Cabin
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 5 - Nov 6
Total with taxes and fees
Shenandoah Valley Yurt
A wooden cabin with a staircase leading to a covered porch, surrounded by a gravel area and a wooden fence.

15. 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 forested area with a fire pit and Adirondack chairs.

16. 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
$178 nightly
The price is $203
Nov 8 - Nov 9
Total with taxes and fees
Moonfire Farm Shenandoah region cozy getaway
A modern house with a deck, surrounded by a well-maintained lawn and trees.

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (64 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
$318 nightly
The price is $330
Nov 9 - Nov 10
Total with taxes and fees
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
A wooden deck with two sliding glass doors leading to a covered patio area.

18. 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
A wooden staircase leading to a deck with a railing, a potted plant, and a metal chair.

19. Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Stanardsville
9.8 out of 10, Exceptional, (61 reviews)
"The apartment was clean and well maintained! The host was also supper communicative giving us plenty of ideas of where to go and what to do in the area."
United States
samantha b.
$157 nightly
The price is $178
Nov 9 - Nov 10
Total with taxes and fees
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
A small, single-story wooden cabin with a white-framed door and a small porch.

20. 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, (17 reviews)
"Very comfortable and clean space. Plenty of room for 1 or 2 people. Check in and out instructions were very detailed. Price was very affordable compared to the nicer hotels in town who were charging $200 to $300 a night. Kind of out in the country but its easy to get to and from town, pretty straight stretch. I was only there in the evenings and everything was very quiet and peaceful."
United States
emily
$204 nightly
The price is $215
Nov 18 - Nov 19
Total with taxes and fees
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
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 Hotel Reviews

DoubleTree by Hilton Hotel Charlottesville

DoubleTree by Hilton Hotel Charlottesville

8/10 Good
"N/A"
Lance 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Hotel Charlottesville

Find out more about Madison

Everything you need to know about Madison 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Madison?

Yes, we offer vacation rentals near popular points of interest in Madison, or you can select a more secluded option if you're looking for relaxation. Madison is known for its mountain views.

What's the top vacation rental in Madison?

Mountainside Villas at Massanutten by Tripforth: Visitors like this Madison vacation home rental. It is located near skiing and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Amenities like kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your vacation with amenities like an outdoor tennis court.

How many vacation rentals will I find in Madison?

With 24 Expedia vacation rentals, you're sure to find just the right place for your Madison stay.

What can I see and do in Madison?

Shenandoah National Park and Rapidan River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Early Mountain Vineyards and Madison Plaza.

What are vacation rentals like in Madison?

Vacation rentals are private accommodations you can book for a short or long stay in Madison. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.