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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Madison holiday rentals

The Cabin at the Lake

The Cabin at the Lake
Madison
9.8 out of 10, Exceptional, (57 reviews)
"I was a great stay. Serene and secluded."
United States
Eugene L.
The price is NZ$514
includes taxes & fees
9 July - 10 July
The Cabin at the Lake

Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (17 reviews)
"Host was communicative with easy check in instructions. Loved the location in relation to a local brewery and winery. The bakery and breakfast restaurant on the Main Street were fantastic as easy to walk to. "
United States
Sophie
The price is NZ$441
includes taxes & fees
6 July - 7 July
Historic Madison Eagle Inn

Charming 4-bedroom house in Madison centrally located!

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was excellent. The host was responsive to every need. The house was beautiful. The view from the front window is beautiful!! The bathtub and shower in the main bathroom is luxurious!! We would be willing to stay there again."
United States
Lori K.
The price is NZ$694
includes taxes & fees
12 July - 13 July
Charming 4-bedroom house in Madison centrally located!

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

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
The price is NZ$715
includes taxes & fees
12 July - 13 July
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

BLOCK Shenandoah Crossing 3br

BLOCK Shenandoah Crossing 3br
Gordonsville
The price is NZ$3,219
includes taxes & fees
6 July - 7 July
BLOCK Shenandoah Crossing 3br

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, (112 reviews)
"Great place"
United States
Ouali
The price is NZ$415
includes taxes & fees
8 July - 9 July
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Elegant Cottage on 600 Acre Horse & Livestock Farm

Elegant Cottage on 600 Acre Horse & Livestock Farm
Gordonsville
9.8 out of 10, Exceptional, (157 reviews)
"Third time here. Love staying here"
United States
Isabelle S.
The price is NZ$511
includes taxes & fees
6 July - 7 July
Elegant Cottage on 600 Acre Horse & Livestock Farm

Mountains & Privacy: Perfect for Couples/Sm Groups

Mountains & Privacy: Perfect for Couples/Sm Groups
Stanley
10.0 out of 10, Exceptional, (72 reviews)
"Perfect cabin for our fall getaway for 2! Hot tub was the perfect place to relax after exploring the beautiful scenery near by! "
United States
Crystal S.
The price is NZ$577
includes taxes & fees
6 July - 7 July
Mountains & Privacy: Perfect for Couples/Sm Groups

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Gordonsville
9.8 out of 10, Exceptional, (88 reviews)
"Location stood out.4th time at the Pond House."
United States
Jeff C.
The price is NZ$532
includes taxes & fees
6 July - 7 July
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Rileyville
10.0 out of 10, Exceptional, (329 reviews)
"The most perfect spot to spend a couple of days. I can't wait to go back and sit on the deck for more sunsets."
United States
Stacie T.
The price is NZ$487
includes taxes & fees
6 July - 7 July
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten.

Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten.
Elkton
10.0 out of 10, Exceptional, (102 reviews)
"House was perfect for our family of five. Very private and quiet. Highly recommended. "
United States
James
The price is NZ$549
includes taxes & fees
6 July - 7 July
Quiet, clean, jacuzzi hot tub. hidden gem, families. Skyline Park & Massanutten.

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (27 reviews)
"The property is perfect for a weekend getaway for a couple of a small family with kids. I really enjoyed my stay and would recommend it."
United States
Ronald
The price is NZ$395
includes taxes & fees
6 July - 7 July
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Skyline View: New build! A+ views! Spacious!

Skyline View: New build! A+ views! Spacious!
Stanley
10.0 out of 10, Exceptional, (80 reviews)
"Beautiful view!"
United States
Michelle H.
Skyline View: New build! A+ views! Spacious!

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (38 reviews)
"Great service!"
United States
Chuck B.
The price is NZ$468
includes taxes & fees
6 July - 7 July
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

The Black Bear Lodge: Amazing Mountain Views!

The Black Bear Lodge: Amazing Mountain Views!
Stanley
9.8 out of 10, Exceptional, (82 reviews)
"Great views. Cabin is well organized and clean. Owners/Managers are quick to respond and easy to work with. Our third stay at this cabin."
United States
Wayne S.
The price is NZ$577
includes taxes & fees
7 July - 8 July
The Black Bear Lodge: Amazing Mountain Views!

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville
10.0 out of 10, Exceptional, (34 reviews)
"Absolutely lovely place to stay. Stunning views and conveniently located to so many of the local attractions. Will definitely come back someday."
United States
Kirby R.
The price is NZ$551
includes taxes & fees
6 July - 7 July
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

6BR Luxe Log Retreat | Hot Tub, Forest-Backed, Resort Access

6BR Luxe Log Retreat | Hot Tub, Forest-Backed, Resort Access
McGaheysville
9.0 out of 10, Wonderful, (112 reviews)
"The house was beautiful and great for our family. "
United States
Jenny R.
The price is NZ$973
includes taxes & fees
7 July - 8 July
6BR Luxe Log Retreat | Hot Tub, Forest-Backed, Resort Access

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
9.6 out of 10, Exceptional, (90 reviews)
"I was able to stay a couple of days at this lovely house. Loved the location and the stream right next to the house. Perfect size for us and our dog. We hope to stay again in the future. "
United States
Tiffany G.
The price is NZ$433
includes taxes & fees
6 July - 7 July
The House in the Holla at the foot of Shenandoah National Park

The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (47 reviews)
"Had a great stay! In a perfect location close to all the wineries and downtown of Gordonsville. House was very clean and had everything we needed. "
United States
Marisa G.
The price is NZ$785
includes taxes & fees
6 July - 7 July
The Ranch at Wine Country - Complimentary Bottle!

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville
9.6 out of 10, Exceptional, (34 reviews)
"Had a wonderful time and highly recommend staying. "
United States
Kathy M.
The price is NZ$849
includes taxes & fees
6 July - 7 July
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Madison Hotel Reviews

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 favorite 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 depends 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 NZ$415 per night. Entering your travel dates in the search wizard you might find 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?

Massanutten Resort by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, an arcade/games room and free WiFi to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Madison?

With 23 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 Lawrence Beasley Park.

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.