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

Madison Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Madison holiday 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 HK$1,091
HK$1,979 total
includes taxes & fees
2 Nov - 3 Nov
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.
The price is HK$1,236
HK$2,293 total
includes taxes & fees
25 Oct - 26 Oct
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)
"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 HK$1,887
HK$3,681 total
includes taxes & fees
1 Nov - 2 Nov
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.
The price is HK$1,936
HK$3,710 total
includes taxes & fees
25 Oct - 26 Oct
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A cabin with a wooden deck, two chairs, a red door, and a window.

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

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (23 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.
The price is HK$636
HK$882 total
includes taxes & fees
26 Oct - 27 Oct
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A cabin with a dining table set for a meal, a bicycle, and a sign indicating the name 'Vangelis'.

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, (147 reviews)
"Loved everything about my stay, customer service was amazing and I’m definitely making this an animal visit!"
United States
Promise
The price is HK$1,130
HK$1,636 total
includes taxes & fees
19 Nov - 20 Nov
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, (34 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is HK$974
HK$1,538 total
includes taxes & fees
25 Oct - 26 Oct
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, (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
The price is HK$981
HK$1,769 total
includes taxes & fees
22 Oct - 23 Oct
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A house with a brick chimney, a small window, and a wooden deck.

9. 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.
The price is HK$848
HK$1,288 total
includes taxes & fees
27 Oct - 28 Oct
Newly renovated entire guest suite in Orange County.
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

10. 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.
The price is HK$918
HK$1,938 total
includes taxes & fees
27 Oct - 28 Oct
The House in the Holla at the foot of Shenandoah National Park
A round table with a grill in the center, surrounded by white Adirondack chairs, set on a wooden deck with a forest background.

11. 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.
The price is HK$731
HK$3,015 total
includes taxes & fees
26 Oct - 27 Oct
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
A forested area with a fire pit and Adirondack chairs.

12. 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 HK$1,059
HK$1,686 total
includes taxes & fees
27 Oct - 28 Oct
Moonfire Farm Shenandoah region cozy getaway
A wooden staircase leading to a deck with a railing, a potted plant, and a metal chair.

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, (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
The price is HK$1,130
HK$1,467 total
includes taxes & fees
2 Nov - 3 Nov
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
A kitchen with white cabinets, a granite countertop, and a tiled floor.

14. 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
The price is HK$647
HK$1,640 total
includes taxes & fees
9 Nov - 10 Nov
Red Brush Cottage Property
A modern house with a deck, surrounded by a well-maintained lawn and trees.

15. 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.
The price is HK$1,233
HK$2,810 total
includes taxes & fees
9 Nov - 10 Nov
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
A small, single-story wooden cabin with a white-framed door and a small porch.

16. 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, (15 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is HK$699
HK$1,769 total
includes taxes & fees
27 Oct - 28 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A wooden deck with two sliding glass doors leading to a covered patio area.

17. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"Clean room and great space."
United States
Makenzi
The price is HK$345
HK$1,073 total
includes taxes & fees
26 Oct - 27 Oct
Creekside Villa 1 bedroom
Outdoor dining

18. 10 mins from Shenandoah National Park ~ Cozy Cabin

10 mins from Shenandoah National Park ~ Cozy Cabin
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay there, it was only a night but the cottage has everything you need for a relaxing trip. The hot tub was super easy to use and the view of the woods was beautiful."
United States
Tamsin D.
The price is HK$1,107
HK$2,207 total
includes taxes & fees
26 Oct - 27 Oct
10 mins from Shenandoah National Park ~ Cozy Cabin
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

19. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (31 reviews)
"Wonderful, communicative host in a beautiful, quiet area. Would definitely come back again!"
United States
MiaMaria C.
The price is HK$1,028
HK$2,204 total
includes taxes & fees
4 Nov - 5 Nov
Shenandoah Valley Yurt
A room with a wooden bench, a rug, and two windows with a welcome sign.

20. Charming Cottage w/ Incredible Views & Firepit

Charming Cottage w/ Incredible Views & Firepit
Stanley
10.0 out of 10, Exceptional, (25 reviews)
"Pet friendly. Great scenery. Hot tub. Fire pit. Very relaxing and comfortable."
United States
Laura M.
The price is HK$1,104
HK$2,901 total
includes taxes & fees
27 Oct - 28 Oct
Charming Cottage w/ Incredible Views & Firepit
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

English Inn of Charlottesville

English Inn of Charlottesville

8/10 Good
"Great place to stay. The gym was the only problem. Way too small and too few pieces of equipment (one of which was broken). Need to fix that and then great."
JAMES 2-night trip
Posted 8 hours ago
English Inn of Charlottesville

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

  • View our selection of featured holiday rentals in Madison
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  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

Look no further and take a look at our great range of rental properties in Madison!

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?

Mountainside Villas at Massanutten by Tripforth: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as kitchenware and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court.

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.