Madison Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 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
The price is CA $196
CA $342 total
includes taxes & fees
Dec 1 - Dec 2
Historic Madison Eagle Inn
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

2. 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)
"The home met all our family’s needs during a weekend stay for a party at nearby farm. The layout and outdoor spaces were a bonus. In fact, the view of Hawksbill Mountain from the porch while enjoying our morning coffee: priceless. And importantly easy access to Rt 29 and the town but yet secluded and bucolic."
United States
B D.
The price is CA $362
CA $659 total
includes taxes & fees
Dec 3 - Dec 4
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.

3. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
9.0 out of 10, Wonderful, (2 reviews)
"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.
The price is CA $372
CA $671 total
includes taxes & fees
Nov 12 - Nov 13
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

4. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (68 reviews)
"Perfect little getaway."
United States
Vernon M.
The price is CA $222
CA $397 total
includes taxes & fees
Nov 12 - Nov 13
The Cabin at the Lake
A wooden cabin with a porch, stone pathway, and outdoor seating.

5. Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A

Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
Madison
10.0 out of 10, Exceptional, (11 reviews)
"This house was perfect for our weekend stay. It was very clean and had a well stocked kitchen and bathrooms. There was plenty of space for our family of 5 to spread out and relax. The beds were all comfortable to sleep in too."
United States
Megan F.
The price is CA $199
CA $393 total
includes taxes & fees
Nov 29 - Nov 30
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

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, (156 reviews)
"Picture perfect, seemless check in and the coffee and maple oatmeal were my cherry on top!"
United States
Rachel
The price is CA $179
CA $267 total
includes taxes & fees
Dec 10 - Dec 11
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, bar stools, and pendant lighting.

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, (37 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is CA $180
CA $266 total
includes taxes & fees
Nov 12 - Nov 13
Barn Apartment on Farm Near Old Rag and 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, (35 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
The price is CA $176
CA $259 total
includes taxes & fees
Nov 15 - Nov 16
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A cabin with a wooden deck, two chairs, a red door, and a window.

9. 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, (25 reviews)
"We had a terrific, unplugged time visiting the farm and Shenandoah National Park. Thanks!"
United States
Maria N.
The price is CA $114
CA $146 total
includes taxes & fees
Nov 17 - Nov 18
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

10. 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, (19 reviews)
"Nice home, we enjoyed our stay. "
United States
Carol T.
The price is CA $302
CA $634 total
includes taxes & fees
Nov 12 - Nov 13
Charming 3-bdrm house in Ruckersville offering great location for your vacation
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

11. 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, (74 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is CA $629
CA $1,033 total
includes taxes & fees
Nov 12 - Nov 13
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

12. 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, (103 reviews)
"Very peaceful and quiet, but relatively close to Charlottesville."
United States
Victor V.
The price is CA $165
CA $318 total
includes taxes & fees
Nov 17 - Nov 18
The House in the Holla at the foot of Shenandoah National Park
S'mores anyone?

13. Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Sperryville
10.0 out of 10, Exceptional, (34 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is CA $360
CA $851 total
includes taxes & fees
Nov 17 - Nov 18
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A cabin with a large window overlooking a flowing river, a wooden interior, and a small table with a patterned tablecloth.

14. Log Cabin on the River

Log Cabin on the River
Stanardsville
9.8 out of 10, Exceptional, (47 reviews)
"The cabin exceeded expectations! Such a beautiful place to stay. "
United States
Melanie B.
The price is CA $289
CA $419 total
includes taxes & fees
Nov 14 - Nov 15
Log Cabin on the River
A wooden staircase leading to a deck with a railing, a potted plant, and a metal chair.

15. 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, (62 reviews)
"The apartment was clean and well maintained! The host was also supper communicative giving us plenty of ideas of where to go and what to do in the area."
United States
samantha b.
The price is CA $203
CA $240 total
includes taxes & fees
Nov 17 - Nov 18
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

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

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
The price is CA $405
CA $905 total
includes taxes & fees
Nov 12 - Nov 13
Walk to Old Rag | Hot Tub | Mountain Farmhouse
A forested area with a fire pit and Adirondack chairs.

17. 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
The price is CA $178
CA $271 total
includes taxes & fees
Nov 12 - Nov 13
Moonfire Farm Shenandoah region cozy getaway
A living room with a stone fireplace, black leather sofa, and a flat-screen TV mounted on the wall.

18. 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)
"The home was great, lots of space and sleeping areas. The farm itself was amazing. Would definitely stay again. Having a golf cart was a so fun."
United States
B S.
The price is CA $508
CA $592 total
includes taxes & fees
Nov 16 - Nov 17
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
A modern house with a deck, surrounded by a well-maintained lawn and trees.

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (64 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is CA $211
CA $469 total
includes taxes & fees
Nov 12 - Nov 13
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Two people sitting at a wooden table outdoors, holding glasses of a beverage.

20. Elegant Chalet on a 600-Acre Horse and Cattle Ranch

Elegant Chalet on a 600-Acre Horse and Cattle Ranch
Gordonsville
9.8 out of 10, Exceptional, (159 reviews)
"Great secluded property on a beautiful setting. "
United States
Todd R.
The price is CA $280
CA $359 total
includes taxes & fees
Nov 12 - Nov 13
Elegant Chalet on a 600-Acre Horse and Cattle Ranch
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

A large, multi-story hotel with a central courtyard, surrounded by lush green fields and trees.
Round Hill Inn

Round Hill Inn

Round Hill Inn
Orange

10/10 Excellent

Great location for what we needed. Clean and the staff were very friendly
Canada
Sarah
Reviewed September 17, 2025
Round Hill Inn

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard 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.

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.