A large pink building with a blue roof, surrounded by a well-maintained lawn and dense trees.

Madison Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Madison holiday rentals

Dining

Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (18 reviews)
"Host was communicative with easy check in instructions. Loved the location in relation to a local brewery and winery. The bakery and breakfast restaurant on the Main Street were fantastic as easy to walk to. "
United States
Sophie
The price is AU$361
includes taxes & fees
29 July - 30 July
Historic Madison Eagle Inn
Coffee/tea maker, fridge, microwave, oven

Charming 4-bedroom house in Madison centrally located!

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (3 reviews)
"Our stay was excellent. The host was responsive to every need. The house was beautiful. The view from the front window is beautiful!! The bathtub and shower in the main bathroom is luxurious!! We would be willing to stay there again."
United States
Lori K.
The price is AU$530
includes taxes & fees
29 July - 30 July
Charming 4-bedroom house in Madison centrally located!
Terrace/patio

The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (61 reviews)
"I was a great stay. Serene and secluded."
United States
Eugene L.
The price is AU$419
includes taxes & fees
29 July - 30 July
The Cabin at the Lake
Interior

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

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
8.0 out of 10, Very good, (1 review)
"Positive Highlights: quiet location still close to Skyline Drive, amenities, fresh interior recently modernized, love for details (charging cables, coffee bar, etc)"
United States
Birgit W.
The price is AU$646
includes taxes & fees
30 July - 31 July
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Suite, 1 Queen Bed

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.4 out of 10, Exceptional, (117 reviews)
"Loved this place and can’t wait to go back there."
United States
Susannah
The price is AU$298
includes taxes & fees
27 Aug - 28 Aug
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Interior

Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Etlan
10.0 out of 10, Exceptional, (23 reviews)
"Fantastic place, so relaxing and beautiful. Host was responsive and extremely helpful. "
United States
Mack
The price is AU$317
includes taxes & fees
9 Aug - 10 Aug
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Exterior

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.6 out of 10, Exceptional, (17 reviews)
"Great host. Super clean. Excellent driving directions and walking info to get to the cabin. Awesome solution for people who love camping"
United States
Patrick
The price is AU$164
includes taxes & fees
3 Aug - 4 Aug
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Exterior

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (27 reviews)
"The property is perfect for a weekend getaway for a couple of a small family with kids. I really enjoyed my stay and would recommend it."
United States
Ronald
The price is AU$324
includes taxes & fees
10 Aug - 11 Aug
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
TV, fireplace, video games, DVD player

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Etlan
9.4 out of 10, Exceptional, (72 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is AU$1,047
includes taxes & fees
30 July - 31 July
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Property grounds

Elegant Cottage on 600 Acre Horse & Livestock Farm

Elegant Cottage on 600 Acre Horse & Livestock Farm
Gordonsville
9.8 out of 10, Exceptional, (158 reviews)
"So beautiful very relaxing highly recommend "
United States
John Wright S.
The price is AU$416
includes taxes & fees
10 Aug - 11 Aug
Elegant Cottage on 600 Acre Horse & Livestock Farm
Exterior

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

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Gordonsville
9.8 out of 10, Exceptional, (88 reviews)
"Location stood out.4th time at the Pond House."
United States
Jeff C.
The price is AU$434
includes taxes & fees
10 Aug - 11 Aug
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Property grounds

Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Gordonsville
9.8 out of 10, Exceptional, (142 reviews)
"This was a beautiful property. The horse pastures were right outside the cottage. There is a hiking trail on the property that was a nice surprise. Highly recommend this cottage and would stay again. "
United States
Rosemary C.
The price is AU$287
includes taxes & fees
10 Aug - 11 Aug
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Property grounds

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

The House in the Holla at the foot of Shenandoah National Park
Stanardsville
9.8 out of 10, Exceptional, (93 reviews)
"Great location and cute house! Loved the stream along the property."
United States
McGowan B.
The price is AU$375
includes taxes & fees
10 Aug - 11 Aug
The House in the Holla at the foot of Shenandoah National Park
Smart TV, ping pong, books

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (24 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is AU$851
includes taxes & fees
29 July - 30 July
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Terrace/patio

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

Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Stanardsville
10.0 out of 10, Exceptional, (55 reviews)
"This was a beautiful and quiet place to spend your nights between hiking and exploring Shenandoah national park! Highly recommend and would come back!"
United States
Anna
The price is AU$269
includes taxes & fees
3 Aug - 4 Aug
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Property grounds

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Sperryville
10.0 out of 10, Exceptional, (26 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is AU$822
includes taxes & fees
29 July - 30 July
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Smart TV, fireplace, books

The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (47 reviews)
"Had a great stay! In a perfect location close to all the wineries and downtown of Gordonsville. House was very clean and had everything we needed. "
United States
Marisa G.
The price is AU$627
includes taxes & fees
10 Aug - 11 Aug
The Ranch at Wine Country - Complimentary Bottle!
Smart TV, fireplace, DVD player, table football

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville
9.6 out of 10, Exceptional, (34 reviews)
"Had a wonderful time and highly recommend staying. "
United States
Kathy M.
The price is AU$688
includes taxes & fees
10 Aug - 11 Aug
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Property grounds

Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
10.0 out of 10, Exceptional, (37 reviews)
"It was a very pleasant stay. We chatted it up with Stuart the owner he was very nice. The place was super clean and we had everything we needed. We would totally stay again. Great experience!"
United States
Matt
The price is AU$311
includes taxes & fees
11 Aug - 12 Aug
Moonfire Farm Shenandoah region cozy getaway
Exterior

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (56 reviews)
"Great get away for the family. Quiet and relaxing. "
United States
Darla
The price is AU$492
includes taxes & fees
26 Aug - 27 Aug
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
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.
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Top Madison Hotel Reviews

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"As always, our one day stay was certainly enjoyable!"
Donald 1-night trip
Posted 5 hours ago
English Inn of Charlottesville

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, 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 AU$298 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 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 Resort by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, an arcade/games room and free WiFi to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

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.