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

Madison Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Madison vacation rentals

Terrace/patio

The Cabin at the Lake

The Cabin at the Lake
Madison
9.8 out of 10, Exceptional, (60 reviews)
"I was a great stay. Serene and secluded."
United States
Eugene L.
$263 nightly
The price is $292
Jul 16 - Jul 17
Total with taxes and fees
The Cabin at the Lake
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.
$339 nightly
The price is $377
Jul 16 - Jul 17
Total with taxes and fees
Charming 4-bedroom house in Madison centrally located!
Dining

Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (17 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
$242 nightly
The price is $252
Jul 27 - Jul 28
Total with taxes and fees
Historic Madison Eagle Inn
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.
$367 nightly
The price is $408
Jul 16 - Jul 17
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Property grounds

Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (45 reviews)
"Wonderful rental! Host very friendly! "
United States
Anonymous traveler
$153 nightly
The price is $164
Jul 16 - Jul 17
Total with taxes and fees
Newly renovated entire guest suite in Orange County.
Property grounds

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
9.8 out of 10, Exceptional, (90 reviews)
"Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is."
United States
Lisa S.
$443 nightly
The price is $466
Aug 2 - Aug 3
Total with taxes and fees
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
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.
$288 nightly
The price is $309
Jul 20 - Jul 21
Total with taxes and fees
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Smart TV, fireplace, foosball, table tennis

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (38 reviews)
"Very easy Checkin and lots of outdoor space"
United States
Bryan T.
$248 nightly
The price is $266
Jul 20 - Jul 21
Total with taxes and fees
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
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.
$273 nightly
The price is $293
Jul 16 - Jul 17
Total with taxes and fees
Elegant Cottage on 600 Acre Horse & Livestock Farm
Fridge, microwave, oven, stovetop

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

Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and family friendly."
United States
Tracy
$180 nightly
The price is $193
Jul 20 - Jul 21
Total with taxes and fees
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Smart TV, fireplace, DVD player, foosball

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.
$451 nightly
The price is $484
Jul 20 - Jul 21
Total with taxes and fees
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
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)
"Loved the privacy we felt the whole time we were there"
United States
Erica S.
$186 nightly
The price is $200
Jul 20 - Jul 21
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
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.
$423 nightly
The price is $454
Jul 20 - Jul 21
Total with taxes and fees
The Ranch at Wine Country - Complimentary Bottle!
Terrace/patio

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

“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville
10.0 out of 10, Exceptional, (34 reviews)
"Tracy was very welcoming and friendly. The accommodation was great."
United States
Linda N.
$326 nightly
The price is $350
Jul 31 - Aug 1
Total with taxes and fees
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Dining

Completely private suite with tub,kitchen, living room, & private entrance

Completely private suite with tub,kitchen, living room, & private entrance
Washington
10.0 out of 10, Exceptional, (20 reviews)
"Perfect location in town"
United States
Mona T.
$208 nightly
The price is $224
Jul 20 - Jul 21
Total with taxes and fees
Completely private suite with tub,kitchen, living room, & private entrance
Dining

Entire Colonial Private 3BR House Beside The Inn.Fast WiFi,tub,queen size bed

Entire Colonial Private 3BR House Beside The Inn.Fast WiFi,tub,queen size bed
Washington
10.0 out of 10, Exceptional, (127 reviews)
"We loved this accomodation! In a great little town and near the skyline drive. It was so peaceful and comfortable - only wish we had stayed longer!"
United Kingdom
Lily P.
$260 nightly
The price is $280
Jul 30 - Jul 31
Total with taxes and fees
Entire Colonial Private 3BR House Beside The Inn.Fast WiFi,tub,queen size bed
Interior

Mint Cottage at Little Washington - a modern, spacious retreat with a view

Mint Cottage at Little Washington - a modern, spacious retreat with a view
Washington
10.0 out of 10, Exceptional, (13 reviews)
"Perfect spot for a couple visiting the area or dining at the Inn. "
United States
Greg S.
$405 nightly
The price is $467
Jul 16 - Jul 17
Total with taxes and fees
Mint Cottage at Little Washington - a modern, spacious retreat with a view
TV, fireplace

Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!

Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!
Keswick
10.0 out of 10, Exceptional, (45 reviews)
"Amazing property! Beautiful views from the front porch, very clean house that is nicely updated. We had all we needed for our spring break getaway."
United States
Jessica N.
$351 nightly
The price is $399
Jul 16 - Jul 17
Total with taxes and fees
Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!
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, (22 reviews)
"Fantastic place, so relaxing and beautiful. Host was responsive and extremely helpful. "
United States
Mack
$188 nightly
The price is $209
Jul 21 - Jul 22
Total with taxes and fees
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
$101 nightly
The price is $112
Jul 19 - Jul 20
Total with taxes and fees
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
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

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

10/10 Excellent
"Personal de primera , muy limpio piscina bien laundry bien este hotel vale la pena"
Carlos Jose Sanchez 2-night trip
Posted 7 hours ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Madison in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $198 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Massanutten Resort by Tripforth: Visitors like this Madison vacation home rental. It is located near skiing and has an outdoor pool, an arcade game room, and free WiFi to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Madison?

With 23 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 Lawrence Beasley Park.

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.