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

Madison Vacation Rentals

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Our top choices for Madison vacation rentals

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
The price is CA $165
CA $316 total
includes taxes & fees
Aug 25 - Aug 26
Historic Madison Eagle Inn

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.
The price is CA $282
CA $584 total
includes taxes & fees
Sep 13 - Sep 14
Charming 4-bedroom house in Madison centrally located!

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.
The price is CA $217
CA $404 total
includes taxes & fees
Aug 25 - Aug 26
The Cabin at the Lake

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.
The price is CA $323
CA $637 total
includes taxes & fees
Aug 30 - Aug 31
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

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, (129 reviews)
"Love This place wish I could I stay longer"
United States
Troy
The price is CA $178
CA $263 total
includes taxes & fees
Aug 25 - Aug 26
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

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
The price is CA $146
CA $239 total
includes taxes & fees
Aug 28 - Aug 29
Barn Apartment on Farm Near Old Rag and Shenandoah National Park

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, (18 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
The price is CA $111
CA $155 total
includes taxes & fees
Aug 31 - Sep 1
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

8. 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
The price is CA $172
CA $309 total
includes taxes & fees
Aug 25 - Aug 26
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

9. 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.
The price is CA $303
CA $402 total
includes taxes & fees
Aug 26 - Aug 27
Elegant Cottage on 600 Acre Horse & Livestock Farm

10. 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.
The price is CA $613
CA $1,007 total
includes taxes & fees
Aug 25 - Aug 26
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

11. “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, (35 reviews)
"Tracy was very welcoming and friendly. The accommodation was great."
United States
Linda N.
The price is CA $308
CA $445 total
includes taxes & fees
Aug 25 - Aug 26
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.

12. '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.
The price is CA $323
CA $428 total
includes taxes & fees
Aug 25 - Aug 26
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

13. 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, (56 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
The price is CA $198
CA $256 total
includes taxes & fees
Aug 29 - Aug 30
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

14. 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.
The price is CA $161
CA $337 total
includes taxes & fees
Aug 25 - Aug 26
The House in the Holla at the foot of Shenandoah National Park

15. 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)
"Peace setting surrounded by horse pastures."
United States
Stephen R.
The price is CA $206
CA $275 total
includes taxes & fees
Aug 25 - Aug 26
Servants' Cottage on 600 Acre Working Horse/Cattle Estate

16. 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.
The price is CA $353
CA $822 total
includes taxes & fees
Aug 25 - Aug 26
Walk to Old Rag | Hot Tub | Mountain Farmhouse

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
The price is CA $186
CA $294 total
includes taxes & fees
Aug 25 - Aug 26
Moonfire Farm Shenandoah region cozy getaway

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
The price is CA $220
CA $266 total
includes taxes & fees
Aug 25 - Aug 26
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

19. Mountains & Privacy: Perfect for Couples/Sm Groups

Mountains & Privacy: Perfect for Couples/Sm Groups
Stanley
10.0 out of 10, Exceptional, (72 reviews)
"Perfect cabin for our fall getaway for 2! Hot tub was the perfect place to relax after exploring the beautiful scenery near by! "
United States
Crystal S.
The price is CA $325
CA $423 total
includes taxes & fees
Aug 25 - Aug 26
Mountains & Privacy: Perfect for Couples/Sm Groups

20. Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.

Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Gordonsville
9.4 out of 10, Exceptional, (39 reviews)
"Very easy Checkin and lots of outdoor space"
United States
Bryan T.
The price is CA $303
CA $369 total
includes taxes & fees
Aug 25 - Aug 26
Escape the City; Country Living at its Best at our 600 acre 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

Find out more about Madison

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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.