Madison Holiday Rentals from €167: 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. Another good choice for your trip to Madison is Old Rag View Horse Farm with Log Lodge and Treehouse .

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Our top choices for Madison holiday rentals

A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

1. Historic Madison Eagle Inn

Madison

Tracy

includes taxes & fees

4 Oct - 5 Oct

A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

2. The Cabin at the Lake

Madison

Leti H.

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

3. Charming 4-bedroom house in Madison centrally located!

Madison

Lori K.

includes taxes & fees

23 Sept - 24 Sept

A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

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

Madison

Birgit W.

includes taxes & fees

23 Sept - 24 Sept

A cabin with a wooden deck, two chairs, a red door, and a window.

5. Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Etlan

Patrick

includes taxes & fees

23 Sept - 24 Sept

A black RV with a wooden deck and steps leading to a covered area.

6. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

Humberto

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with a central island, bar stools, and pendant lighting.

7. Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Etlan

Ikuo

includes taxes & fees

23 Sept - 24 Sept

A two-story house with a stone facade, a front porch, and a well-maintained lawn.

8. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Stanardsville

Ronald

includes taxes & fees

24 Sept - 25 Sept

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Top Madison Hotel Reviews

Mimslyn Inn Historic Hotels Of America

10/10 Excellent

"We enjoyed the stay at Mimslyn very much! It is walking distance to town if you don’t mind walking up the hill which we did not. The rooms were a bit small and I would recommend removing a piece of furniture or two to give guests a bit more space but the rooms seemed clean. We traveled with an infant and didn’t realize how much we would need a fridge and microwave so that was a bit of a challenge, but the staff was incredibly accommodating with allowing us to store our baby medical items with them. I cannot express enough how wonderful the staff is here. The only thing that would give me pause about staying here again is the lack of a mini fridge, but all in all the staff truly made the experience wonderful."

DoubleTree by Hilton Hotel Charlottesville

8/10 Good

"The lobby and a few other areas had been updated and were very nice. The late night guest services gentleman who checked us in was super friendly and made us feel welcome. And, of course, there were the warm cookies! The room was also very nice and had all the amenities needed for comfort--plenty of options for recharging devices, refrigerator, microwave, and coffee pot. Unfortunately, the bathroom was out of date and needed some maintenance. The bathtub had a few black marks that, at first, looked like dirt, but were actually wear marks or stains. The bottom of the door was ragged and beyond repair. In addition to that, the bath gel was nearly empty--better attention about replenishing is needed. The best part of the room, however, was the bed. Incredibly comfortable mattress and crisp, fresh sheets. Best sleep in a long time!"

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 €167 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. 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 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 Madison Plaza.

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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