Madison Vacation Rentals from CA $281: Short-Term Rentals for 2026

Q: What's the top vacation rental in Madison?

Mountainside Villas at Massanutten by Tripforth : You might want to consider this vacation home rental near Madison, which is located near skiing and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Amenities like kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your vacation with amenities like 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 vacation 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

CA $351 total

includes taxes & fees

Oct 4 - Oct 5

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

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

Madison

Lori K.

CA $625 total

includes taxes & fees

Sep 28 - Sep 29

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

3. The Cabin at the Lake

Madison

Leti H.

CA $415 total

includes taxes & fees

Sep 28 - Sep 29

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.

CA $655 total

includes taxes & fees

Sep 28 - Sep 29

A cabin with a dining table set for a meal, a bicycle, and a sign indicating the name 'Vangelis'.

5. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

Promise

CA $281 total

includes taxes & fees

Oct 1 - Oct 2

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

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

Etlan

Patrick

CA $159 total

includes taxes & fees

Sep 29 - Sep 30

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

CA $263 total

includes taxes & fees

Sep 28 - Sep 29

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

CA $317 total

includes taxes & fees

Sep 28 - Sep 29

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Top Madison Hotel Reviews

Comfort Inn & Suites Charlottesville Hollymead Town Center

10/10 Excellent

"Clean room, helpful staff, good continental breakfast with stir-fried veggies eggs, fruits, bagels and pastri3s"

Kimpton The Forum Hotel by IHG

10/10 Excellent

"This was my first time staying at a Kimpton property and I was really impressed! We loved everything about it. The bath products you provided were amazing, the robes were super comfortable, the pillows and the bed were extremely comfortable. The breakfast at the restaurant was delicious! And, the grounds and arboretum were gorgeous! Thank you for a wonderful experience!"

Sonesta ES Suites Charlottesville University

10/10 Excellent

"Was pleasantly surprised by this hotel. Very comfortable room, kitchenette and full sized fridge was welcome, super clean. Breakfast was typical but good (even the coffee!). Only hitch was a slightly abrupt front desk clerk (the other couple I dealt with were lovely). Parking was tight tho I did get a spot. Didn’t have my dog with me but looked like a great place for pets, big grassy area with benches and bins for waste bags."

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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison vacation rentals we have selected for you start as low as CA $281 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 vacation 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 vacation.

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 vacation rentals in Madison?

Yes, we offer vacation rentals near popular points of interest in Madison, or you can select a more secluded option if you're looking for relaxation. Madison is known for its mountain views.

What's the top vacation rental in Madison?

Mountainside Villas at Massanutten by Tripforth: You might want to consider this vacation home rental near Madison, which is located near skiing and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Amenities like kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your vacation with amenities like 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 vacation rentals will I find in Madison?

With 24 Expedia vacation rentals, you're sure 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 vacation rentals like in Madison?

Vacation rentals are private accommodations you can book for a short or long stay in Madison. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

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Our top choices for Madison vacation rentals

1. Historic Madison Eagle Inn

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

3. The Cabin at the Lake

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

5. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

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

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

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

9. Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

10. Servants' Cottage on 600 Acre Working Horse/Cattle Estate

11. The House in the Holla at the foot of Shenandoah National Park

12. “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

13. Elegant Cottage on 600 Acre Horse & Livestock Farm

14. Moonfire Farm Shenandoah region cozy getaway

15. Walk to Old Rag | Hot Tub | Mountain Farmhouse

16. Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

17. 'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

18. 10 mins from Shenandoah National Park ~ Cozy Cabin

19. Newly renovated entire guest suite in Orange County.

20. Whispering Hillside -Coffee Bar, Hot Tub Fire Pit

Find vacation rentals that suit your style

Top Madison Hotel Reviews

Comfort Inn & Suites Charlottesville Hollymead Town Center

Skyland

Kimpton The Forum Hotel by IHG

Red Roof Inn Charlottesville

Mimslyn Inn Historic Hotels Of America

Quality Inn Luray

Big Meadows Lodge

Sonesta ES Suites Charlottesville University

DoubleTree by Hilton Hotel Charlottesville

Find out more about Madison

Frequently asked questions

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