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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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

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
$242 nightly
The price is $252
Nov 2 - Nov 3
Total with taxes and fees
Historic Madison Eagle Inn
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

2. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (66 reviews)
"Perfect little getaway."
United States
Vernon M.
$282 nightly
The price is $314
Oct 25 - Oct 26
Total with taxes and fees
The Cabin at the Lake
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

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

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (4 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.
$418 nightly
The price is $466
Oct 18 - Oct 19
Total with taxes and fees
Charming 4-bedroom house in Madison centrally located!
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

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.
$425 nightly
The price is $473
Oct 19 - Oct 20
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
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

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.4 out of 10, Exceptional, (147 reviews)
"Loved everything about my stay, customer service was amazing and I’m definitely making this an animal visit!"
United States
Promise
$184 nightly
The price is $208
Nov 15 - Nov 16
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, bar stools, and pendant lighting.

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, (32 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
$172 nightly
The price is $191
Oct 20 - Oct 21
Total with taxes and fees
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A cabin with a wooden deck, two chairs, a red door, and a window.

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

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (22 reviews)
"Hose was excellent, great communication, helpful, answered questions, even returned items inadvertently left behind. Location was great for activities around the national park and caverns."
United States
Tracy P.
$101 nightly
The price is $112
Oct 18 - Oct 19
Total with taxes and fees
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
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+

Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Stanardsville
10.0 out of 10, Exceptional, (33 reviews)
"Stayed here for a weekend while hiking Old Rag in Shenandoah. Cozy little place that was well equipped with all the amenities we needed! It's conveniently located close to Shenandoah as well as plenty of vineyards. Would not hesitate to stay here again the next time we're in the area!"
United States
Jason
$199 nightly
The price is $225
Oct 19 - Oct 20
Total with taxes and fees
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

9. 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, (99 reviews)
"Clean, sweet, and quiet. Perfect for a weekend away from everything "
United States
Piper G.
$217 nightly
The price is $246
Oct 18 - Oct 19
Total with taxes and fees
The House in the Holla at the foot of Shenandoah National Park
A house with a brick chimney, a small window, and a wooden deck.

10. 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.
$153 nightly
The price is $164
Oct 19 - Oct 20
Total with taxes and fees
Newly renovated entire guest suite in Orange County.
A forested area with a fire pit and Adirondack chairs.

11. 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
$189 nightly
The price is $216
Oct 27 - Oct 28
Total with taxes and fees
Moonfire Farm Shenandoah region cozy getaway
A wooden staircase leading to a deck with a railing, a potted plant, and a metal chair.

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, (60 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
Oct 19 - Oct 20
Total with taxes and fees
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
A modern house with a deck, surrounded by a well-maintained lawn and trees.

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (62 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
$343 nightly
The price is $358
Nov 9 - Nov 10
Total with taxes and fees
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
A round table with a grill in the center, surrounded by white Adirondack chairs, set on a wooden deck with a forest background.

14. NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE

NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
Stanley
9.8 out of 10, Exceptional, (26 reviews)
"Very beautifully decorated, clean and well maintained cottage. We appreciate all detail info provided about the house and surroundings and especially the warm welcome with lights and hot tub ready to use. It's located in more secluded location but not too far from local attractions, so we enjoyed hiking in Shanendoah NP. Wisteria Winery 5 min from cottage is awesome too."
United States
Marta D.
$333 nightly
The price is $384
Oct 26 - Oct 27
Total with taxes and fees
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

15. Charming 3-bdrm house in Ruckersville offering great location for your vacation

Charming 3-bdrm house in Ruckersville offering great location for your vacation
Ruckersville
9.8 out of 10, Exceptional, (17 reviews)
"Nice home, we enjoyed our stay. "
United States
Carol T.
$416 nightly
The price is $472
Oct 18 - Oct 19
Total with taxes and fees
Charming 3-bdrm house in Ruckersville offering great location for your vacation
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

16. 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, (46 reviews)
"Beautiful property and family friendly."
United States
Tracy
$181 nightly
The price is $194
Oct 18 - Oct 19
Total with taxes and fees
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A grassy field with a wooden fence, trees, and a distant building.

17. 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
Oct 19 - Oct 20
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
A wooden deck with a railing, a bench, and a table, overlooking a forested area.

18. Daniels Mountain Lodge, large cabin by Shenandoah

Daniels Mountain Lodge, large cabin by Shenandoah
Stanardsville
9.8 out of 10, Exceptional, (13 reviews)
"The cabin was spacious and we enjoyed the large porch. "
United States
Patrick G.
$530 nightly
The price is $631
Oct 18 - Oct 19
Total with taxes and fees
Daniels Mountain Lodge, large cabin by Shenandoah
A kitchen with white cabinets, a granite countertop, and a tiled floor.

19. Red Brush Cottage Property

Red Brush Cottage Property
Elkton
9.0 out of 10, Wonderful, (2 reviews)
"Basic, updated cottage that met our needs for an overnight with family. Sparsely furnished but worked for us. Thanks."
United States
Margaret
$211 nightly
The price is $213
Nov 9 - Nov 10
Total with taxes and fees
Red Brush Cottage Property
A log cabin with a large window and a wooden door.

20. Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy

Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy
Stanley
8.4 out of 10, Very good, (86 reviews)
"It was a beautiful cabin, exactly what we needed to get away from the city and just disconnect. If you’re not comfortable driving on mountain roads, just something to think about. Overall an amazing little getaway. "
United States
Mike B.
$367 nightly
The price is $423
Oct 30 - Oct 31
Total with taxes and fees
Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy
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

Big Meadows Lodge

Big Meadows Lodge

10/10 Excellent
"It was big. Lots of meadows. Like a big meadow. With places to sleep. A veritable big meadows lodge."
Andrew 4-night trip
Posted less than an hour ago
Big Meadows Lodge

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 $112 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: Visitors like this Madison vacation home rental. It 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.

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.