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

Madison Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Madison vacation rentals

Dining

1. Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
United States
Tracy
$228 nightly
The price is $237
Oct 4 - Oct 5
Total with taxes and fees
Historic Madison Eagle Inn
Coffee/tea maker, fridge, microwave, oven

2. 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.
$394 nightly
The price is $439
Sep 20 - Sep 21
Total with taxes and fees
Charming 4-bedroom house in Madison centrally located!
Terrace/patio

3. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (62 reviews)
"Great view and access to the lake!"
United States
Leti H.
$263 nightly
The price is $292
Sep 21 - Sep 22
Total with taxes and fees
The Cabin at the Lake
Interior

4. 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.
$412 nightly
The price is $459
Sep 20 - Sep 21
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Exterior

5. 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, (20 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
Sep 20 - Sep 21
Total with taxes and fees
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
View from property

6. 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, (138 reviews)
"Fantastic stay!! Everything was perfect."
United States
Humberto
$169 nightly
The price is $191
Sep 21 - Sep 22
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Interior

7. 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, (28 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
$153 nightly
The price is $171
Sep 22 - Sep 23
Total with taxes and fees
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Property grounds

8. 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)
"Great secluded property on a beautiful setting. "
United States
Todd R.
$271 nightly
The price is $291
Sep 21 - Sep 22
Total with taxes and fees
Elegant Cottage on 600 Acre Horse & Livestock Farm
Property grounds

9. 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, (143 reviews)
"The cottage had everything you need."
United States
William J.
$186 nightly
The price is $200
Sep 21 - Sep 22
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Exterior

10. '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.
$290 nightly
The price is $311
Sep 24 - Sep 25
Total with taxes and fees
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Exterior

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

Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (29 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
$199 nightly
The price is $225
Sep 20 - Sep 21
Total with taxes and fees
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Terrace/patio

12. 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
9.8 out of 10, Exceptional, (58 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
$165 nightly
The price is $187
Sep 21 - Sep 22
Total with taxes and fees
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Property grounds

13. Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
9.8 out of 10, Exceptional, (42 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
$203 nightly
The price is $232
Oct 5 - Oct 6
Total with taxes and fees
Moonfire Farm Shenandoah region cozy getaway
Smart TV, table tennis, books

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

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (26 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
$495 nightly
The price is $546
Sep 20 - Sep 21
Total with taxes and fees
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Smart TV, fireplace, books

15. The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (50 reviews)
"The absolute cleanest place I've ever stayed. Just a clean smell when arriving. My whole family there for skydiving for only one night Very pet friendly and close attention to every detail. Bad storm resulting in losing power but host was very responsive and problem resolved. Great parking and decor. 10 out of 10"
United States
Irma S.
$423 nightly
The price is $454
Sep 22 - Sep 23
Total with taxes and fees
The Ranch at Wine Country - Complimentary Bottle!
Smart TV, fireplace, video games, DVD player

16. Skyline View: New build! A+ views! Spacious!

Skyline View: New build! A+ views! Spacious!
Stanley
10.0 out of 10, Exceptional, (85 reviews)
"Great stay"
United States
Danny K.
$394 nightly
The price is $442
Sep 20 - Sep 21
Total with taxes and fees
Skyline View: New build! A+ views! Spacious!
Property grounds

17. 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, (97 reviews)
"The house is very clean and supplied with everything you will need."
United States
Mike I.
$217 nightly
The price is $246
Sep 20 - Sep 21
Total with taxes and fees
The House in the Holla at the foot of Shenandoah National Park
Property grounds

18. 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)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
United States
vishal k.
$165 nightly
The price is $177
Oct 12 - Oct 13
Total with taxes and fees
Newly renovated entire guest suite in Orange County.
Outdoor spa tub

19. The Black Bear Lodge: Amazing Mountain Views!

The Black Bear Lodge: Amazing Mountain Views!
Stanley
9.8 out of 10, Exceptional, (85 reviews)
"Great views. Cabin is well organized and clean. Owners/Managers are quick to respond and easy to work with. Our third stay at this cabin."
United States
Wayne S.
$292 nightly
The price is $335
Sep 27 - Sep 28
Total with taxes and fees
The Black Bear Lodge: Amazing Mountain Views!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Comfort Inn & Suites Charlottesville Hollymead Town Center

Comfort Inn & Suites Charlottesville Hollymead Town Center

10/10 Excellent
"Clean & well maintained"
Chaitanya 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Charlottesville Hollymead Town Center

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 $165 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?

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 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 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.