Madison Holiday Rentals from €190: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Madison has to offer?

Mountainside Villas at Massanutten by Tripforth : This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court.

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Our top choices for Madison holiday rentals

The Cabin at the Lake

Madison

Donna H.

includes taxes & fees

24 Jun - 25 Jun

Historic Madison Eagle Inn

Madison

Sophie

includes taxes & fees

6 Jul - 7 Jul

Charming 4-bedroom house in Madison centrally located!

Madison

Lori K.

includes taxes & fees

23 Jun - 24 Jun

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

Madison

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

Ouali

includes taxes & fees

30 Jun - 1 Jul

Mountainside Villas at Massanutten by Tripforth

McGaheysville

Dominick

includes taxes & fees

23 Jun - 24 Jun

Massanutten Chalet

McGaheysville

Kim E.

includes taxes & fees

25 Jun - 26 Jun

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Rileyville

Aaron A.

includes taxes & fees

12 Jul - 13 Jul

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Top Madison Hotel Reviews

Hyatt Place Charlottesville

10/10 Excellent

"Genuinely nice people and the property is great. Spotless room, halls, elevators, etc. "

English Inn of Charlottesville

10/10 Excellent

"The assistant manager that we talked to a couple of times (and checked us in) was very helpful in offering suggestions on activities/dining. The room was spacious and a good value. Everything was clean. The afternoon tea and cookies was nice. They have a large pool available; however, the advertising stated it was heated, but it felt pretty cold. Overall, good value and would stay again!"

Holiday Inn Charlottesville-Univ Area by IHG

10/10 Excellent

"Low drama, exactly what you'd expect from a Holiday Inn. Fanciest place in the world? Not at all. But it's spotlessly clean, the beds are big and comfy, the rooms are properly AC-equipped, and everyone is friendly. Even the coffee wasn't too bad."

Skyland

10/10 Excellent

"We stayed 2 nights in June 2026 and were given what was called a premium room. I don’t know what that meant. But the room was located on the back ridge behind the playground with a great sunset view! It was not rustic (no camper here!) and had all the amenities you need - fridge, Starbucks pods for Kuerig, back porch with 2 chairs and side table, kitchen table with 2 chairs. TV only had like 10 channels but given how little service and tech there is in the park, that seemed fine to me! The restaurant here is good too- but definitely sit in the dining room or outside patio for premium views (tap room is not as nice). I’ve never stayed inside a national park before so that was a great experience. Day 1 we traveled north and dined in Front Royal and day 2 we traveled south and ate in Waynesboro (definitely recommend the River burger bar there - awesome spot!). Since there’s no service in park I recommend getting the GuideAlong app so you can see the park map and know all the hotspots to check out- it works even in the sos cell service zone)."

Massanutten Resort

10/10 Excellent

"Where can I begin, first of all from tve moment I arrive EVERYONE had a smile on their faces. The energy was amazin! Then when we got inside of our room, I felt like I was at home. Very cozy and peaceful. I’ll be back sooner rather than later. This is my new peace! Thank you all for an awesome and amazing weekend!"

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, 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 €190 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?

Mountainside Villas at Massanutten by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court.

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.

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