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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Madison vacation rentals

Dining

1. 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
$242 nightly
The price is $252
Aug 5 - Aug 6
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.
$355 nightly
The price is $395
Aug 11 - Aug 12
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, (61 reviews)
"I was a great stay. Serene and secluded."
United States
Eugene L.
$263 nightly
The price is $292
Aug 5 - Aug 6
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
Aug 6 - Aug 7
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Suite, 1 Queen Bed | 1 bedroom, desk, laptop workspace, bed sheets

5. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.6 out of 10, Exceptional, (121 reviews)
"Love This place wish I could I stay longer"
United States
Troy
$199 nightly
The price is $225
Aug 10 - Aug 11
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Interior

6. 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
$165 nightly
The price is $184
Aug 10 - Aug 11
Total with taxes and fees
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Exterior

7. 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
Aug 9 - Aug 10
Total with taxes and fees
Moonshine Glamping Cabin near Old Rag Mountain in 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
Aug 5 - Aug 6
Total with taxes and fees
Elegant Cottage on 600 Acre Horse & Livestock Farm
Exterior

9. 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
$196 nightly
The price is $222
Aug 5 - Aug 6
Total with taxes and fees
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
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.
$288 nightly
The price is $309
Aug 5 - Aug 6
Total with taxes and fees
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Property grounds

11. 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.
$185 nightly
The price is $199
Aug 5 - Aug 6
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
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
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
$164 nightly
The price is $186
Aug 9 - Aug 10
Total with taxes and fees
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
TV, fireplace, video games, DVD player

13. 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.
$658 nightly
The price is $732
Aug 9 - Aug 10
Total with taxes and fees
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Property grounds

14. Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
10.0 out of 10, Exceptional, (38 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
$193 nightly
The price is $220
Aug 18 - Aug 19
Total with taxes and fees
Moonfire Farm Shenandoah region cozy getaway
Terrace/patio

15. “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.
$298 nightly
The price is $320
Aug 10 - Aug 11
Total with taxes and fees
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Smart TV, fireplace, books

16. The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (48 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
Aug 5 - Aug 6
Total with taxes and fees
The Ranch at Wine Country - Complimentary Bottle!
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, (95 reviews)
"Great location and cute house! Loved the stream along the property."
United States
McGowan B.
$216 nightly
The price is $245
Aug 9 - Aug 10
Total with taxes and fees
The House in the Holla at the foot of Shenandoah National Park
Coffee/tea maker, fridge, microwave, oven

18. 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, (45 reviews)
"Beautiful property and family friendly."
United States
Tracy
$180 nightly
The price is $193
Aug 5 - Aug 6
Total with taxes and fees
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Smart TV, table tennis, books

19. 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.
$513 nightly
The price is $567
Aug 5 - Aug 6
Total with taxes and fees
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Smart TV, fireplace, DVD player, foosball

20. 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, (35 reviews)
"Had a wonderful time and highly recommend staying. "
United States
Kathy M.
$451 nightly
The price is $484
Aug 5 - Aug 6
Total with taxes and fees
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
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

Comfort Inn & Suites Charlottesville Hollymead Town Center

Comfort Inn & Suites Charlottesville Hollymead Town Center

8/10 Good
"clean room"
John 2-night trip
Posted less than an hour 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 $225 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 25 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.