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

Madison Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Madison holiday rentals

A hallway with a wooden bench, a red door, and a framed picture on the wall.

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
The price is AU$354
includes taxes & fees
2 Nov - 3 Nov
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, (67 reviews)
"Perfect little getaway."
United States
Vernon M.
The price is AU$395
includes taxes & fees
27 Oct - 28 Oct
The Cabin at the Lake
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

3. 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 AU$653
includes taxes & fees
27 Oct - 28 Oct
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.

4. 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$665
includes taxes & fees
27 Oct - 28 Oct
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A glass enclosure with a view of a forest interior, including a bed and various plants.

5. 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, (150 reviews)
"Clean room, nice place for weekend."
United States
Heng
The price is AU$309
includes taxes & fees
24 Nov - 25 Nov
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A cabin with a wooden deck, two chairs, a red door, and a window.

6. 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, (23 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.
The price is AU$163
includes taxes & fees
27 Oct - 28 Oct
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A modern kitchen with a central island, bar stools, and pendant lighting.

7. 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, (35 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
Barn Apartment on Farm Near Old Rag and 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
The price is AU$326
includes taxes & fees
28 Oct - 29 Oct
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A house with a brick chimney, a small window, and a wooden deck.

9. 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.
The price is AU$236
includes taxes & fees
27 Oct - 28 Oct
Newly renovated entire guest suite in Orange County.
A round table with a grill in the center, surrounded by white Adirondack chairs, set on a wooden deck with a forest background.

10. NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE

NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
Stanley
9.8 out of 10, Exceptional, (26 reviews)
"Very beautifully decorated, clean and well maintained cottage. We appreciate all detail info provided about the house and surroundings and especially the warm welcome with lights and hot tub ready to use. It's located in more secluded location but not too far from local attractions, so we enjoyed hiking in Shanendoah NP. Wisteria Winery 5 min from cottage is awesome too."
United States
Marta D.
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
A forested area with a fire pit and Adirondack chairs.

11. 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
The price is AU$307
includes taxes & fees
27 Oct - 28 Oct
Moonfire Farm Shenandoah region cozy getaway
A modern house with a deck, surrounded by a well-maintained lawn and trees.

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (63 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is AU$485
includes taxes & fees
9 Nov - 10 Nov
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a herringbone wood floor.

13. 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.
The price is AU$274
includes taxes & fees
8 Nov - 9 Nov
RiverFront Country Home with Blue Mountain Views
A kitchen with white cabinets, a granite countertop, and a tiled floor.

14. 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
The price is AU$297
includes taxes & fees
9 Nov - 10 Nov
Red Brush Cottage Property
A grassy field with a wooden fence, trees, and a distant building.

15. 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.
The price is AU$262
includes taxes & fees
27 Oct - 28 Oct
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
A small, single-story wooden cabin with a white-framed door and a small porch.

16. 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
The price is AU$324
includes taxes & fees
27 Oct - 28 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Outdoor dining

17. 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.
The price is AU$444
includes taxes & fees
17 Nov - 18 Nov
10 mins from Shenandoah National Park ~ Cozy Cabin
A wooden deck with two black mugs on a table, a covered grill, and a bench.

18. Secluded log cabin, fireplace, wi-fi, hot tub on deck!! Secluded on 6 acres

Secluded log cabin, fireplace, wi-fi, hot tub on deck!! Secluded on 6 acres
Stanley
7.8 out of 10, Good, (91 reviews)
"We enjoyed the quiet and relaxing stay at the cabin . The hot tub was what we needed after a day of hiking nearby waterfalls."
United States
Shannon M.
The price is AU$463
includes taxes & fees
29 Oct - 30 Oct
Secluded log cabin, fireplace, wi-fi, hot tub on deck!! Secluded on 6 acres
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, (15 reviews)
"Cozy cabin, perfect for a solo retreat to rest and relax."
United States
Rachael C.
The price is AU$197
includes taxes & fees
5 Nov - 6 Nov
Creekside Villa 1 bedroom
A wooden staircase leading to a deck with a railing, a potted plant, and a metal chair.

20. 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, (60 reviews)
"Great place...beautiful property and it was cozy and clean."
United States
Amy B.
The price is AU$267
includes taxes & fees
2 Nov - 3 Nov
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Massanutten Resort

Massanutten Resort

10/10 Excellent
"Clean, comfortable, quiet room."
Scott 2-night trip
Posted 2 hours ago
Massanutten Resort

Find out more about Madison

Everything you need to know about Madison 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 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Madison holiday 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 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 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 holiday rentals we have selected for you start as low as AU$163 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Madison rentals

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

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay. Madison is known for its mountain views.

What are some of the best holiday rentals that Madison has to offer?

Mountainside Villas at Massanutten by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court.

How many holiday rentals will I find in Madison?

With 24 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.