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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Madison vacation rentals

Dining

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 AED 474
AED 892 total
includes taxes & fees
12 Aug - 13 Aug
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 680
AED 1,472 total
includes taxes & fees
12 Aug - 13 Aug
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, (61 reviews)
"Great view and access to the lake!"
United States
Leti H.
The price is AED 643
AED 1,169 total
includes taxes & fees
20 Aug - 21 Aug
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 804
AED 1,631 total
includes taxes & fees
16 Aug - 17 Aug
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Exterior detail

5. 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 AED 327
AED 836 total
includes taxes & fees
15 Aug - 16 Aug
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Property grounds

6. Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
9.8 out of 10, Exceptional, (90 reviews)
"The absolute nicest, cleanest Vrbo I have ever stayed at! Great communication from the host, the property did not disappoint. It was well stocked with everything needed. And very clear directions for using the property and a terrific folder with area information. Will return."
United States
Janet G.
The price is AED 871
AED 1,798 total
includes taxes & fees
12 Aug - 13 Aug
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Exterior

7. '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 1,151 total
includes taxes & fees
12 Aug - 13 Aug
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Smart TV, fireplace, foosball, table tennis

8. 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 AED 808
AED 993 total
includes taxes & fees
12 Aug - 13 Aug
Escape the City; Country Living at its Best at our 600 acre horse/cattle farm.
Property grounds

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 AED 808
AED 1,084 total
includes taxes & fees
12 Aug - 13 Aug
Elegant Cottage on 600 Acre Horse & Livestock Farm
Coffee/tea maker, fridge, microwave, oven

10. 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 717 total
includes taxes & fees
12 Aug - 13 Aug
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Smart TV, fireplace, DVD player, foosball

11. 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 AED 1,469
AED 1,801 total
includes taxes & fees
12 Aug - 13 Aug
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Property grounds

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)
"This was a beautiful property. The horse pastures were right outside the cottage. There is a hiking trail on the property that was a nice surprise. Highly recommend this cottage and would stay again. "
United States
Rosemary C.
The price is AED 551
AED 737 total
includes taxes & fees
12 Aug - 13 Aug
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Smart TV, fireplace, books

13. The Ranch at Wine Country - Complimentary Bottle!

The Ranch at Wine Country - Complimentary Bottle!
Gordonsville
10.0 out of 10, Exceptional, (48 reviews)
"Had a great stay! In a perfect location close to all the wineries and downtown of Gordonsville. House was very clean and had everything we needed. "
United States
Marisa G.
The price is AED 973
AED 1,667 total
includes taxes & fees
12 Aug - 13 Aug
The Ranch at Wine Country - Complimentary Bottle!
Terrace/patio

14. “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 AED 823
AED 1,191 total
includes taxes & fees
12 Aug - 13 Aug
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Dining

15. 1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.

1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
Washington
10.0 out of 10, Exceptional, (20 reviews)
"Perfect location in town"
United States
Mona T.
The price is AED 457
AED 853 total
includes taxes & fees
18 Aug - 19 Aug
1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
Dining

16. 1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .

1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
Washington
10.0 out of 10, Exceptional, (128 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is AED 586
AED 1,036 total
includes taxes & fees
18 Aug - 19 Aug
1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
Interior

17. Mint Cottage at Little Washington - a modern, spacious retreat with a view

Mint Cottage at Little Washington - a modern, spacious retreat with a view
Washington
10.0 out of 10, Exceptional, (13 reviews)
"Perfect spot for a couple visiting the area or dining at the Inn. "
United States
Greg S.
The price is AED 1,320
AED 1,729 total
includes taxes & fees
17 Aug - 18 Aug
Mint Cottage at Little Washington - a modern, spacious retreat with a view
Interior

18. 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 AED 474
AED 740 total
includes taxes & fees
23 Aug - 24 Aug
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Exterior

19. 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, (17 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 367
AED 491 total
includes taxes & fees
10 Sep - 11 Sep
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
TV, fireplace, video games, DVD player

20. 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 AED 1,636
AED 2,688 total
includes taxes & fees
12 Aug - 13 Aug
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
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

Skyland

Skyland

10/10 Excellent
"Loved the location! Amazing views had we not stayed in a storm."
Michael 1-night trip
Posted 3 hours ago
Skyland

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.