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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$246 nightly
The price is $257
Sep 8 - Sep 9
Total with taxes and fees
Historic Madison Eagle Inn
Terrace/patio

2. 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.
$267 nightly
The price is $297
Sep 1 - Sep 2
Total with taxes and fees
The Cabin at the Lake
Coffee/tea maker, fridge, microwave, oven

3. 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.
$383 nightly
The price is $426
Sep 13 - Sep 14
Total with taxes and fees
Charming 4-bedroom house in Madison centrally located!
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.
$417 nightly
The price is $464
Sep 1 - Sep 2
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
View from property

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, (133 reviews)
"Love This place wish I could I stay longer"
United States
Troy
$167 nightly
The price is $189
Sep 7 - Sep 8
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, (24 reviews)
"Beautiful and unique property. The place was shiny clean and Jen was very communicative and helpful!"
United States
Dan S.
$156 nightly
The price is $174
Sep 1 - Sep 2
Total with taxes and fees
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Exterior

7. 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
$200 nightly
The price is $227
Sep 1 - Sep 2
Total with taxes and fees
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
Property grounds

8. 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, (96 reviews)
"Great location and cute house! Loved the stream along the property."
United States
McGowan B.
$220 nightly
The price is $249
Sep 1 - Sep 2
Total with taxes and fees
The House in the Holla at the foot of Shenandoah National Park
Exterior detail

9. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.8 out of 10, Exceptional, (11 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
$215 nightly
The price is $227
Sep 1 - Sep 2
Total with taxes and fees
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Terrace/patio

10. 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, (57 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 2 - Sep 3
Total with taxes and fees
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Exterior detail

11. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Clean room and great space."
United States
Makenzi
$124 nightly
The price is $137
Sep 1 - Sep 2
Total with taxes and fees
Creekside Villa 1 bedroom
Exterior

12. Wood Haven Lodge 2 bedroom

Wood Haven Lodge 2 bedroom
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Had a great stay. Property was clean and cozy. Beautiful views. Loved the farm setting! "
United States
Timea Z.
$181 nightly
The price is $199
Sep 1 - Sep 2
Total with taxes and fees
Wood Haven Lodge 2 bedroom
Property grounds

13. 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)
"The cottage had everything you need."
United States
William J.
$189 nightly
The price is $203
Sep 1 - Sep 2
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Exterior

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (58 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
$340 nightly
The price is $354
Sep 1 - Sep 2
Total with taxes and fees
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Living area

15. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay with a very responsive and flexible host! Check in and check out was very easy"
United States
Ron G.
$220 nightly
The price is $240
Sep 2 - Sep 3
Total with taxes and fees
Shenandoah Valley Yurt
Coffee/tea maker, fridge, microwave, oven

16. RiverFront Country Home with Blue Mountain Views

RiverFront Country Home with Blue Mountain Views
Free Union
9.6 out of 10, Exceptional, (39 reviews)
"Enjoyed our stay."
United States
Katrecia B.
$142 nightly
The price is $161
Sep 3 - Sep 4
Total with taxes and fees
RiverFront Country Home with Blue Mountain Views
Property grounds

17. Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
9.8 out of 10, Exceptional, (40 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
Sep 1 - Sep 2
Total with taxes and fees
Moonfire Farm Shenandoah region cozy getaway
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
$183 nightly
The price is $196
Sep 1 - Sep 2
Total with taxes and fees
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Outdoor dining

19. Secluded log cabin, fireplace, wi-fi, hot tub on deck!! Secluded on 6 acres

Secluded log cabin, fireplace, wi-fi, hot tub on deck!! Secluded on 6 acres
Stanley
8.0 out of 10, Very Good, (89 reviews)
"We enjoyed the quiet and relaxing stay at the cabin . The hot tub was what we needed after a day of hiking nearby waterfalls."
United States
Shannon M.
$289 nightly
The price is $333
Sep 3 - Sep 4
Total with taxes and fees
Secluded log cabin, fireplace, wi-fi, hot tub on deck!! Secluded on 6 acres
Property grounds

20. 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.
$275 nightly
The price is $295
Sep 1 - Sep 2
Total with taxes and fees
Elegant Cottage on 600 Acre Horse & Livestock 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

Big Meadows Lodge

Big Meadows Lodge

10/10 Excellent
"Excelente lugar para relajarse y olvidarse de la rutina"
Yngrid 1-night trip
Posted 12 hours 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 $161 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.