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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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
The price is AED 496
AED 878 total
includes taxes & fees
4 Oct - 5 Oct
Historic Madison Eagle Inn
Coffee/tea maker, fridge, microwave, oven

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 AED 804
AED 1,521 total
includes taxes & fees
27 Sep - 28 Sep
Charming 4-bedroom house in Madison centrally located!
Terrace/patio

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 AED 579
AED 1,032 total
includes taxes & fees
28 Sep - 29 Sep
The Cabin at the Lake
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.
The price is AED 863
AED 1,590 total
includes taxes & fees
27 Sep - 28 Sep
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Exterior

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, (143 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 AED 465
AED 694 total
includes taxes & fees
30 Sep - 1 Oct
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Exterior

6. 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, (21 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 AED 298
AED 413 total
includes taxes & fees
27 Sep - 28 Sep
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Interior

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, (28 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is AED 431
AED 684 total
includes taxes & fees
28 Sep - 29 Sep
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Exterior

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, (30 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 AED 459
AED 812 total
includes taxes & fees
27 Sep - 28 Sep
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
Terrace/patio

9. 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, (58 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 AED 529
AED 682 total
includes taxes & fees
28 Sep - 29 Sep
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Property grounds

10. 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, (143 reviews)
"The cottage had everything you need."
United States
William J.
The price is AED 551
AED 729 total
includes taxes & fees
28 Sep - 29 Sep
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Property grounds

11. 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, (98 reviews)
"The house is very clean and supplied with everything you will need."
United States
Mike I.
The price is AED 430
AED 882 total
includes taxes & fees
27 Sep - 28 Sep
The House in the Holla at the foot of Shenandoah National Park
Terrace/patio

12. “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, (38 reviews)
"Tracy was very welcoming and friendly. The accommodation was great."
United States
Linda N.
The price is AED 823
AED 1,120 total
includes taxes & fees
27 Sep - 28 Sep
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Property grounds

13. 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 AED 808
AED 1,025 total
includes taxes & fees
29 Sep - 30 Sep
Elegant Cottage on 600 Acre Horse & Livestock Farm
Property grounds

14. 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 AED 496
AED 777 total
includes taxes & fees
5 Oct - 6 Oct
Moonfire Farm Shenandoah region cozy getaway
Smart TV, table tennis, books

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

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
The price is AED 944
AED 2,052 total
includes taxes & fees
27 Sep - 28 Sep
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Coffee/tea maker, fridge, microwave, oven

16. 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 AED 588
AED 709 total
includes taxes & fees
27 Sep - 28 Sep
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Exterior

17. '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 AED 863
AED 1,084 total
includes taxes & fees
29 Sep - 30 Sep
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
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 AED 477
AED 952 total
includes taxes & fees
27 Sep - 28 Sep
10 mins from Shenandoah National Park ~ Cozy Cabin
Property grounds

19. 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 AED 441
AED 650 total
includes taxes & fees
12 Oct - 13 Oct
Newly renovated entire guest suite in Orange County.
Exterior

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (60 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is AED 557
AED 1,204 total
includes taxes & fees
6 Oct - 7 Oct
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
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

Super 8 by Wyndham Charlottesville

Super 8 by Wyndham Charlottesville

10/10 Excellent
"Clean, Quiet and Comfortable bed. Just what we needed!"
Catherine 2-night trip
Posted 1 hour ago
Super 8 by Wyndham Charlottesville

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: You might want to consider this vacation home rental near Madison, which 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. Another good choice for your trip to Madison is Old Rag View Horse Farm with Log Lodge and Treehouse.

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.