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

Madison Holiday Rentals

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Our top choices for Madison holiday 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 NZ$386
includes taxes & fees
25 Aug - 26 Aug
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 NZ$707
includes taxes & fees
14 Sept - 15 Sept
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 NZ$499
includes taxes & fees
24 Aug - 25 Aug
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 NZ$773
includes taxes & fees
30 Aug - 31 Aug
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

5. 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 NZ$206
includes taxes & fees
13 Sept - 14 Sept
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

6. 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, (127 reviews)
"Love This place wish I could I stay longer"
United States
Troy
The price is NZ$323
includes taxes & fees
23 Aug - 24 Aug
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

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, (23 reviews)
"Fantastic place, so relaxing and beautiful. Host was responsive and extremely helpful. "
United States
Mack
The price is NZ$306
includes taxes & fees
23 Aug - 24 Aug
Barn Apartment on Farm Near Old Rag and 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 NZ$376
includes taxes & fees
27 Aug - 28 Aug
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+

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, (96 reviews)
"Great location and cute house! Loved the stream along the property."
United States
McGowan B.
The price is NZ$412
includes taxes & fees
27 Aug - 28 Aug
The House in the Holla at the foot of Shenandoah National Park

10. 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.
The price is NZ$378
includes taxes & fees
21 Aug - 22 Aug
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

11. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"This was a perfect little place for an over night stop for me and my Newfie."
United States
Ingrid K.
The price is NZ$233
includes taxes & fees
23 Aug - 24 Aug
Creekside Villa 1 bedroom

12. 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 NZ$334
includes taxes & fees
8 Sept - 9 Sept
Servants' Cottage on 600 Acre Working Horse/Cattle Estate

13. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (23 reviews)
"Beautiful"
United States
Jennifer
The price is NZ$384
includes taxes & fees
1 Sept - 2 Sept
Shenandoah Valley Yurt

14. 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 NZ$316
includes taxes & fees
28 Aug - 29 Aug
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (57 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is NZ$589
includes taxes & fees
13 Sept - 14 Sept
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit

16. Wood Haven Lodge 2 bedroom

Wood Haven Lodge 2 bedroom
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Had a great stay. Property was clean and cozy. Beautiful views. Loved the farm setting! "
United States
Timea Z.
The price is NZ$346
includes taxes & fees
1 Sept - 2 Sept
Wood Haven Lodge 2 bedroom

17. 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 NZ$325
includes taxes & fees
27 Aug - 28 Aug
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.

18. RiverFront Country Home with Blue Mountain Views

RiverFront Country Home with Blue Mountain Views
Free Union
9.8 out of 10, Exceptional, (38 reviews)
"Enjoyed our stay."
United States
Katrecia B.
The price is NZ$254
includes taxes & fees
31 Aug - 1 Sept
RiverFront Country Home with Blue Mountain Views

19. 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 NZ$360
includes taxes & fees
25 Aug - 26 Aug
Moonfire Farm Shenandoah region cozy getaway

20. Daniels Mountain Lodge, large cabin by Shenandoah

Daniels Mountain Lodge, large cabin by Shenandoah
Stanardsville
9.8 out of 10, Exceptional, (12 reviews)
"The cabin was spacious and we enjoyed the large porch. "
United States
Patrick G.
The price is NZ$1,063
includes taxes & fees
1 Sept - 2 Sept
Daniels Mountain Lodge, large cabin by Shenandoah
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madison holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madison. 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 Madison. 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 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 holiday 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 Madison short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay. Madison is known for its mountain views.

What are some of the best holiday rentals that Madison has to offer?

Massanutten Resort by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, an arcade/games room and free WiFi to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Madison?

With 24 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.