Photo by Phil Martin

Madison Holiday Rentals

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Holiday Rentals in Madison

Old Rag View Horse Farm with Log Lodge and Treehouse
10.0 out of 10, Exceptional, 140 reviews
"Very nice well appointed home. We came in for a nearby family wedding and it was a great place to stay. Try to arrive during the day though as it is a little hard to find at night. But well worth opening and closing a gate or two. Fantastic view. Great space."
Old Rag View Horse Farm with Log Lodge and Treehouse
Massanutten Resort by Tripforth
3.0 star property
7.8 out of 10, Good, 129 reviews
"The only bad thing was the Woodstone pool opens late at 11 am"
Massanutten Resort by Tripforth
Mountainside Villas at Massanutten by Tripforth
3.5 star property
9.0 out of 10, Wonderful, 254 reviews
"The best thing there I love it and enjoy my stay "
Mountainside Villas at Massanutten by Tripforth
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Massanutten's Woodstone Meadows by Tripforth
4.0 star property
9.0 out of 10, Wonderful, 182 reviews
"Perfect and gorgeous resort. It’s located a short outside the central entrance to Shenandoah. "
Massanutten's Woodstone Meadows by Tripforth
The Great Escape - Near everything yet off the beaten path
10.0 out of 10, Exceptional, 356 reviews
"We really enjoyed our time at this little cabin in the valley. Perfect size for couples or a small family. The dogs had a blast running around the fenced in backyard. It had basically every amenity you could ask for and may be the cleanest VRBO I’ve ever stayed in. It is perfectly situated between 2 entrances to Shenandoah National Park. Not terribly far from Shenandoah River State Park (recommended) and walking distance from George Washington National Forest. There are several small towns...
The Great Escape - Near everything yet off the beaten path
Cozy Log Cabin Hot Tub Stone Fireplace Mountain Views Couples Mountain Escape
10.0 out of 10, Exceptional, 55 reviews
"Everything was absolutely perfect! We will definitely be back! The view on the porch was my favorite!"
Cozy Log Cabin Hot Tub Stone Fireplace Mountain Views Couples Mountain Escape
Massanuttens Shenandoah Villas by Tripforth
4.0 star property
7.6 out of 10, Good, 111 reviews
"The hot tub did do work fire place was complicated and romote needs batteries but it was beautiful "
Massanuttens Shenandoah Villas by Tripforth
The Natchez - quiet front porch & rockers.
10.0 out of 10, Exceptional, 95 reviews
"We had a great stay! The cabin was well stocked and Ken made sure we had everything we needed."
The Natchez - quiet front porch & rockers.
Lazy Bear Lodge VA :)
9.8 out of 10, Exceptional, 270 reviews
"Quiet secluded getaway in a cozy country cabin"
Lazy Bear Lodge VA :)
Massanutten Getaway - Great WiFi and Pet friendly
9.6 out of 10, Exceptional, 77 reviews
"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
Helms Mountain Getaway with Hi Speed Internet
9.6 out of 10, Exceptional, 40 reviews
"As always the cabin was clean, comfortable and welcoming. Secluded and the only noise heard was the song birds. The hot tub was perfect and the fire pit was great when it was too rainy for the hot tub. See you again in the fall."
Helms Mountain Getaway with Hi Speed Internet
Massanutten Near Slopes, 2 Masters, Pool Table, Air Hockey, 2 FPs
9.8 out of 10, Exceptional, 280 reviews
"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
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, 151 reviews
"We enjoyed the home but the land even more. Nature is awesome!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Above The Rivers Edge Cabin #1
9.8 out of 10, Exceptional, 153 reviews
"We had a great weekend stay with friends. Beautiful house and close to many things you can do. We will be back! Thanks"
Above The Rivers Edge Cabin #1
The Summit at Massanutten Resort by Tripforth
3.5 star property
9.2 out of 10, Wonderful, 46 reviews
"Beautiful views. Condos were great to stay with family. Love the kitchen. I was able to cook all meals for my family of 4. Jet tubs were dirty so I cleaned it but still felt uneasy taking a bath. Aesthetic of it was nice though. I also loved the options of different activities for adults and family. "
The Summit at Massanutten Resort by Tripforth
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
9.0 out of 10, Wonderful, 114 reviews
"Quiet and lonely was the reason to stay here and it did not disappoint. Will be staying here again."
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
Tree top home in Massanutten next to slopes
9.6 out of 10, Exceptional, 72 reviews
"We enjoyed our 2 nights here…would recommend"
Tree top home in Massanutten next to slopes
Relax at 3100 feet and enjoy the peace and tranquility
9.8 out of 10, Exceptional, 60 reviews
"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
Log cabin home with mountain and ski slope views
9.4 out of 10, Exceptional, 50 reviews
"This is a great house, located very close to the resort. Beautiful views and many amenities made this a wonderful home away from home."
Log cabin home with mountain and ski slope views
Newly Renovated Vacation 4 bedroom Resort House in Massanutten VA!
9.0 out of 10, Wonderful, 17 reviews
"Enjoyed the stay. Very convenient with Massanutten and near JMU. Some nice sight seeing. The property is well maintained and very quick response time by the manager. They are strict on checkout times. I got a message 15 min before checkout warning me that the housekeeper was waiting on us and that I had 15 min. This was after a snafu at checkin where, even though we were an hour late for checkin, the property wasn’t quite ready. Not a big deal, especially since we booked the day before. Loved...
Newly Renovated Vacation 4 bedroom Resort House in Massanutten VA!
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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

Old Rag View Horse Farm with Log Lodge and Treehouse
10.0 out of 10, Exceptional, 140 reviews
"Very nice well appointed home. We came in for a nearby family wedding and it was a great place to stay. Try to arrive during the day though as it is a little hard to find at night. But well worth opening and closing a gate or two. Fantastic view. Great space."
Old Rag View Horse Farm with Log Lodge and Treehouse
English Inn of Charlottesville
3.0 star property
9.0 out of 10, Wonderful, 1,689 reviews
"Did not like the powdered eggs for breakfast! Otherwise, it was the best hotel that we stayed in during a 12 day road trip in which we stayed at a different hotel almost every night."
The price is NZ$183
includes taxes & fees
16 Jun - 17 Jun
English Inn of Charlottesville
Massanutten Resort
2.5 star property
8.0 out of 10, Very good, 318 reviews
"Checkin took a long time. The lady (Zoe) who checked me in was SUPER nice. But there were a lot of young people hanging around doing nothing. The room was comfortable and clean and had a balcony. But the color scheme was awful! Dark green and weird yellow. Too bad there was no breakfast offered. "
The price is NZ$224
includes taxes & fees
18 Jun - 19 Jun
Massanutten Resort
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 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'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 16 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 Sweely Estate Winery.

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
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