Photo by Phil Martin

Holiday Rentals in Madison

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Madison

Property grounds
Old Rag View Horse Farm with Log Lodge and Treehouse
10.0 out of 10, Exceptional, (138)
"Great place in the mountains!"
Old Rag View Horse Farm with Log Lodge and Treehouse
Cozy Log Cabin Hot Tub Stone Fireplace Mountain Views Couples Mountain Escape
10.0 out of 10, Exceptional, (53)
"Beautiful panoramic mountain view! Cabin was very cute and clean. It sits very close to other cabins. We had some difficulty with the front door lock because the battery was low and the TV remote batteries were dead. The bed is very firm and not comfortable at all. The picture/description said there was a swing but the swing has been removed. It has 2 chairs in its place. There was no covering over it so we were unable to use it due to rain. The area is very rural, takes 30-40 minutes to get...
Cozy Log Cabin Hot Tub Stone Fireplace Mountain Views Couples Mountain Escape
Exterior
The Great Escape - Near everything yet off the beaten path
10.0 out of 10, Exceptional, (353)
"Great cabin and terrific hosts!"
The Great Escape - Near everything yet off the beaten path
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
NEW! Game Room-Fireplace-FREE Resort Rec Passes!
10.0 out of 10, Exceptional, (3)
"We have been coming to Massanutten for several years with the family. This home was one of our favorites. The home is roomy.(there were 12 of us)...with the two kitchen tables upstairs for everyone to sit at. The location to the ski resort is perfect. The kids enjoyed the game room. We only stayed for a long weekend but I can see that this house would be great for a week vacation with the two kitchens."
NEW! Game Room-Fireplace-FREE Resort Rec Passes!
Fridge, microwave, oven, stovetop
Newly-built in Massanutten Resort Prime Area, Pool Table, Six Smart TVs, Gas FP
10.0 out of 10, Exceptional, (142)
"We loved staying in this beautiful house! The layout is perfect for entertaining. We had a great time eating, playing pool, playing cards, and just celebrating our son's graduation from JMU. We also had fun participating in the activities at the resort...go-karts, bumper cars, the zip-line, mini golf, fishing at the lakes, and the scenic chair lift! There was something for everyone!"
Newly-built in Massanutten Resort Prime Area, Pool Table, Six Smart TVs, Gas FP
Exterior
Updated! Stunning country home near main street
10.0 out of 10, Exceptional, (33)
"I like that the house had everything I needed included hair dryer, condiments, paper towels, bath towels, shampoo, body wash, laundry detergent, etc. The location is convenient, just minutes away from Luray Caverns and Walmart. I especially enjoyed the stay there of the view with cows you can see from windows!"
The price is €316
per night
30 May - 31 May
Updated! Stunning country home near main street
TV
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
10.0 out of 10, Exceptional, (12)
"This house is a dream!!! Loved everything about it and Ronnie was so accommodating, loved every moment of it"
The price is €853
per night
30 May - 31 May
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
TV, fireplace, DVD player
The Bonnie Retreat in Massanutten
10.0 out of 10, Exceptional, (141)
"We had a wonderful stay and the house exceeded our expectations. The master bathroom was luxurious and the kitchen had everything we needed. Would definitely stay here again!"
The Bonnie Retreat in Massanutten
Property grounds
Beautiful 360 views!
10.0 out of 10, Exceptional, (155)
"Super quaint little cottage, exactly what we needed. The hosts are incredibly sweet and accommodating. The view is of open farmland with mountians in the distance. The sun sets off the back of the cottage and theres a wonderful view. Really wonderful spot!"
Beautiful 360 views!
Outdoor pool
HOT TUB! Fireplace! Mtntop! 5 BDMS! 3 LEVELS OF AWESOME! Pet Friendly
9.8 out of 10, Exceptional, (125)
"My family and the grandparents all had a nice stay at this location. Nice location just outside of Harrisonburg, away from the crowds of students/parents on a very busy weekend, Stay was comfortable and we had plenty of room. Used the big kitchen table to play cards and enjoyed the hot tub on our last night. Thanks!"
HOT TUB! Fireplace! Mtntop! 5 BDMS! 3 LEVELS OF AWESOME! Pet Friendly
Property grounds
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (276)
"This cabin was very comfortable and clean! The kitchen was well equipped for all our needs. The views from the inside are just as spectacular on the outside. While the house is not directly on the reiver that was okay. We figured it would be hard to find a house right on the river with amazing views of the mountains off in the distance. The walk down to the river is not bad. It takes about 7 or so minutes. I highly recommend boots or something other than standard shoes if you go before the dew...
Star view cabin-Riverfront
Lake
Above The Rivers Edge Cabin #1
9.8 out of 10, Exceptional, (152)
"Had a fantabulos time! The cabin had everything we needed."
Above The Rivers Edge Cabin #1
Property grounds
Relax at 3100 feet and enjoy the peace and tranquility
9.8 out of 10, Exceptional, (59)
"The listing was accurate to what is presented. Very clean and easy to find with GPS. Close drive to National Park entrance. Gorgeous views."
Relax at 3100 feet and enjoy the peace and tranquility
Exterior
Massanutten Near Slopes, 2 Masters, Pool Table, Air Hockey, 2 FPs
9.8 out of 10, Exceptional, (280)
"Very clean, large house with great amenities. Kevin was great to work with before and during our stay!"
Massanutten Near Slopes, 2 Masters, Pool Table, Air Hockey, 2 FPs
Exterior
Mountain Top Log home with slope views- Walk to amenities
9.8 out of 10, Exceptional, (52)
"Property is in a great location! So much to do in the area, winter or summer! Home accommodated our group of four adults and 2 children nicely. Very quiet and relaxing Loved the wildlife - a herd of deer - that walked by the back porch each morning and night!"
Mountain Top Log home with slope views- Walk to amenities
Property grounds
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (151)
"We enjoyed the home but the land even more. Nature is awesome!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Fridge, microwave, oven, stovetop
Tree top home in Massanutten next to slopes
9.6 out of 10, Exceptional, (71)
"We have reserved this location on numerous occasions. The home is always perfect: clean, comfortable, and inviting. Mary and Chris are great hosts, and whenever we can get away to Massanutten, we will always look to book this place; our home away from home."
Tree top home in Massanutten next to slopes
Property grounds
Alpine Vista- One of the best views- Brand New Renovations -3 King Beds!
9.6 out of 10, Exceptional, (83)
"Great home with a lovely view of the valley. Great area with the resort, and a nice golf course. House was very accommodating. 9 of us had room to spare."
Alpine Vista- One of the best views- Brand New Renovations -3 King Beds!
Exterior
Helms Mountain Getaway with Hi Speed Internet
9.6 out of 10, Exceptional, (39)
"The only way to describe the view is to see it"
Helms Mountain Getaway with Hi Speed Internet
Pool
Massanutten Getaway - Great WiFi and Pet friendly
9.6 out of 10, Exceptional, (77)
"Had a great stay, will definitely be coming back! Home was clean, spacious, and had lots of entertainment for the kids. Great location to slopes/hiking trails and whatever else you need on the resort."
Massanutten Getaway - Great WiFi and Pet friendly
Don't see what you're looking for?
See all available properties in Madison
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.

Other types of properties in Madison you may be interested in

Property grounds
Old Rag View Horse Farm with Log Lodge and Treehouse
10.0 out of 10, Exceptional, (138)
"Great place in the mountains!"
Old Rag View Horse Farm with Log Lodge and Treehouse
Front of property
English Inn of Charlottesville
3.0 star property
9.0 out of 10, Wonderful, (1667)
"One night stay was perfect for passing through…"
The price is €102
per night
26 May - 27 May
English Inn of Charlottesville
Exterior
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
3.0 star property
9.0 out of 10, Wonderful, (1002)
"The staff was helpful. I am allergic to perfumed products and the room had perfume which gave me a headache."
The price is €116
per night
28 May - 29 May
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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.

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, apart-hotels, 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 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 in Madison close to Sweely Estate Winery, 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's Woodstone Meadows by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, an arcade/games room and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Another good choice for your trip to Madison is Old Rag View Horse Farm with Log Lodge and Treehouse.

How many holiday rentals will I find in Madison?

With 17 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 enjoy the outdoors, whereas family-friendly attractions include Sweely Estate Winery. In the wider area, you’ll find Early Mountain Vineyards and Montpelier.

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.

Recent reviews of Madison properties
Expedia verified reviews

Skyland

Skyland

5/5 Excellent
"Back to nature setting, bucolic panoramas and comfortably shabby chic."
A verified traveller stayed at Skyland
Posted 8 hours ago
Skyland