Photo by Phil Martin

Madison Holiday Rentals

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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, (352)
"Beautiful home has everything you need and more. Our dogs loved the spacious back yard. George Washington Forest is very close. Perfect area to hike and take in all the beauty this location has to offer."
The Great Escape - Near everything yet off the beaten path
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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)
"Nice place to stay, lots of room."
Newly-built in Massanutten Resort Prime Area, Pool Table, Six Smart TVs, Gas FP
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!
TV
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
10.0 out of 10, Exceptional, (11)
"This house is a dream!!! Loved everything about it and Ronnie was so accommodating, loved every moment of it"
The price is NZ$1,473
per night
21 May - 22 May
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
Interior
Massanutten Chalet
10.0 out of 10, Exceptional, (19)
"Owner was so sweet! Extremely helpful, answered so quickly. Came with my friends to go snow tubing and we enjoyed every moment! The home is truly beautiful and everything was perfect. Thank you so much (:"
The price is NZ$611
per night
20 May - 21 May
Massanutten Chalet
Exterior
Lovely home, wonderful location.
10.0 out of 10, Exceptional, (46)
"Quaint cottage with comfortable living space and bonus outdoor lounge chairs to enjoy an afternoon book. The property is within 30 mins of hiking trails in Shenandoah National Park. We really appreciated the ability to get to Main Street high end restaurants and an ice cream shop that had delicious flavor choices. We enjoyed ourselves and the owner was quick responding to questions. "
The price is NZ$489
per night
19 May - 20 May
Lovely home, wonderful location.
Exterior
Updated! Stunning country home near main street
10.0 out of 10, Exceptional, (32)
"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 NZ$510
per night
10 Jun - 11 Jun
Updated! Stunning country home near main street
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, (151)
"It was great clean property quiet secluded just overall great me and the wife really enjoyed it"
Above The Rivers Edge Cabin #1
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
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)
"We enjoyed our stay here. Check in and check out was super simple. The house was clean and appropriately described. The kitchen had ample space for preparing meals. There were games and even toys for the baby. The high chair and crib worked great. We didn’t have any issues. Would stay here again and recommend to friends."
Massanutten Near Slopes, 2 Masters, Pool Table, Air Hockey, 2 FPs
1 bedroom, iron/ironing board, WiFi, bed sheets
Lazy Bear Lodge VA :)
9.8 out of 10, Exceptional, (266)
"We stayed three nights in this perfectly appointed cabin near Shenandoah NP. The kitchen was well equipped, the cabin was lovely, located in a beautiful location. We built a nightly fire outside and used the hot tub. There was also a jet tub in the house which we ran out of time to use. The owner was very responsive and friendly. During our first week of a three week vacation, my husband said staying in this cabin was his favorite part."
Lazy Bear Lodge VA :)
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
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
Fridge, microwave, oven, stovetop
Tree top home in Massanutten next to slopes
9.6 out of 10, Exceptional, (70)
"PERFECT location on a quiet street in Massanutten Resort. We were able to bring our dog and enjoyed walks on the quiet street mornings and evenings w him. Our three boys had a blast at our first-ever visit to Massanutten Resort: we enjoyed the waterpark, zip line, go-karts/bumper cars, putt-putt and explored (but didn’t have a chance to use) the resort recreation centers with pools, basketball, arcades and pool tables. So much to do - we were never bored. Returning to the house for lunch and...
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!
Fridge, microwave, oven, stovetop
Massanutten, easy drive to slopes!, lower level entrance, Pet-friendly, JMU,
9.4 out of 10, Exceptional, (25)
"Very nice house, we stayed here for 5 nights and I’d recommend it to anyone that wants to utilize it for Massanutten or Shenandoah national park."
Massanutten, easy drive to slopes!, lower level entrance, Pet-friendly, JMU,
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, (1663)
"Nice hotel. Very convenient to drive in and out of for a Charlottesville business trip. Very quiet and very close to Bodo's Bagels (big plus). The rooms were very clean, well kept, and I enjoyed my brief visit. Breakfast is adequate and as advertised."
The price is NZ$198
per night
20 May - 21 May
English Inn of Charlottesville
Exterior
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Nice clean room. Great shower"
The price is NZ$217
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madison holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madison. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Madison. Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Madison short-term rentals, that won’t be hard to do.

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