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
Outdoor pool
Massanutten's Woodstone Meadows by Tripforth
4.0 star property
9.0 out of 10, Wonderful, (181)
"Perfect and gorgeous resort. It’s located a short outside the central entrance to Shenandoah. "
Massanutten's Woodstone Meadows by Tripforth
Indoor pool, outdoor pool
Mountainside Villas at Massanutten by Tripforth
3.5 star property
9.0 out of 10, Wonderful, (253)
"Everything was great !"
Mountainside Villas at Massanutten by Tripforth
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Indoor pool, outdoor pool
Massanutten Resort by Tripforth
3.0 star property
7.8 out of 10, Good, (127)
"The only bad thing was the Woodstone pool opens late at 11 am"
Massanutten Resort by Tripforth
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
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
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
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
Indoor pool, outdoor pool
Massanuttens Shenandoah Villas by Tripforth
4.0 star property
7.6 out of 10, Good, (110)
"Great place to begin hold family "
Massanuttens Shenandoah Villas by Tripforth
Exterior
Cozy modern cabin - the squirrel's nest
9.4 out of 10, Exceptional, (199)
"We had a great time staying at the Squirrel’s Nest. The location is secluded but still only 15 minutes away from Shenandoah. The cabin was warm & cozy and a perfect escape from everyday life. Hot tub was a plus!"
Cozy modern cabin - the squirrel's nest
Aerial view
The Summit at Massanutten Resort by Tripforth
3.5 star property
9.2 out of 10, Wonderful, (45)
"Very nice place to stay, enough space, very clean and close to a lot of activities. We would stay here again"
The Summit at Massanutten Resort by Tripforth
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
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
TV, fireplace, DVD player, books
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
9.0 out of 10, Wonderful, (113)
"We had a wonderful time relaxing. The cabin was perfect for us. We hiked the trails and enjoyed the Yoder's market for lunch. Friendly people all around. Definetly coming back."
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing
Pool
Secluded Log Cottage Hot tub on Deck Two Person Whirlpool Tub Fire Place wifi
8.0 out of 10, Very good, (72)
"We had a great time getting away and having a secluded, private and peaceful place to stay. We drove around Shenandoah’s Sky Line Dr and came back to amazing weather and spent a few hours in the hot tub. Accessing the property was easy peasy and the property manager was super quick to respond to any questions. Very relaxing, exactly what we needed! With that being said…the cleanliness was my biggest issue. The futon in the living room is red with black stains all over it, just filthy. We had...
Secluded Log Cottage Hot tub on Deck Two Person Whirlpool Tub Fire Place wifi
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
Exterior
NEW! Game Room-Fireplace-FREE Resort Rec Passes!
10.0 out of 10, Exceptional, (4)
"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
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.

Madison Holiday Home Travel Info

Number of holiday homes
4
Popular accommodation
Madison private holiday homes
Known landmarks
Early Mountain Vineyards
International airport
Charlottesville, VA (CHO-Charlottesville-Albemarle)

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, (1672)
"Was a quite place"
The price is AU$171
includes taxes & fees
27 May - 28 May
English Inn of Charlottesville
2 indoor pools, seasonal outdoor pool, pool loungers, lifeguards on site
Massanutten Resort
2.5 star property
8.0 out of 10, Very good, (304)
"The property was well maintained and clean and we enjoyed the time there. "
The price is AU$197
includes taxes & fees
9 June - 10 June
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.

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 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 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