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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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 ￥21,095
￥38,391 total
includes taxes & fees
Oct 4 - Oct 5
Historic Madison Eagle Inn
Terrace/patio

2. 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 ￥24,611
￥45,655 total
includes taxes & fees
Sep 7 - Sep 8
The Cabin at the Lake
Private kitchen

3. 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 ￥32,033
￥65,568 total
includes taxes & fees
Sep 13 - Sep 14
Charming 4-bedroom house in Madison centrally located!
Exterior

4. Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A

Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
Madison
9.8 out of 10, Exceptional, (10 reviews)
"This house was perfect for our weekend stay. It was very clean and had a well stocked kitchen and bathrooms. There was plenty of space for our family of 5 to spread out and relax. The beds were all comfortable to sleep in too."
United States
Megan F.
The price is ￥26,408
￥50,436 total
includes taxes & fees
Oct 2 - Oct 3
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
Interior

5. 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 ￥36,721
￥71,654 total
includes taxes & fees
Sep 8 - Sep 9
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
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
9.6 out of 10, Exceptional, (20 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 ￥12,657
￥17,565 total
includes taxes & fees
Sep 13 - Sep 14
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
View from property

7. 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, (135 reviews)
"Fantastic stay!! Everything was perfect."
United States
Humberto
The price is ￥20,158
￥29,921 total
includes taxes & fees
Sep 7 - Sep 8
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Interior

8. 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, (25 reviews)
"Beautiful and unique property. The place was shiny clean and Jen was very communicative and helpful!"
United States
Dan S.
The price is ￥20,314
￥31,654 total
includes taxes & fees
Sep 14 - Sep 15
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Exterior

9. 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, (28 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 ￥19,533
￥35,056 total
includes taxes & fees
Sep 8 - Sep 9
Family Getaway; Skiing, Wineries; Skyline Dr; Sleeps 4; Short Stays; EV+
Property grounds

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, (96 reviews)
"Great location and cute house! Loved the stream along the property."
United States
McGowan B.
The price is ￥18,282
￥38,596 total
includes taxes & fees
Sep 8 - Sep 9
The House in the Holla at the foot of Shenandoah National Park
Property grounds

11. 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 ￥23,439
￥31,186 total
includes taxes & fees
Sep 7 - Sep 8
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
Terrace/patio

12. 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, (57 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 ￥22,501
￥29,211 total
includes taxes & fees
Sep 8 - Sep 9
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Exterior detail

13. Creekside Villa 1 bedroom

Creekside Villa 1 bedroom
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Clean room and great space."
United States
Makenzi
The price is ￥6,875
￥21,371 total
includes taxes & fees
Sep 7 - Sep 8
Creekside Villa 1 bedroom
Exterior

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (59 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
The price is ￥23,675
￥55,021 total
includes taxes & fees
Sep 7 - Sep 8
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Property grounds

15. Moonfire Farm Shenandoah region cozy getaway

Moonfire Farm Shenandoah region cozy getaway
Barboursville
9.8 out of 10, Exceptional, (41 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 ￥21,095
￥33,400 total
includes taxes & fees
Sep 7 - Sep 8
Moonfire Farm Shenandoah region cozy getaway
Exterior

16. Wood Haven Lodge 2 bedroom

Wood Haven Lodge 2 bedroom
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Had a great stay. Property was clean and cozy. Beautiful views. Loved the farm setting! "
United States
Timea Z.
The price is ￥13,063
￥30,955 total
includes taxes & fees
Sep 15 - Sep 16
Wood Haven Lodge 2 bedroom
Exterior detail

17. 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)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is ￥13,923
￥35,557 total
includes taxes & fees
Sep 10 - Sep 11
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Living area

18. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay with a very responsive and flexible host! Check in and check out was very easy"
United States
Ron G.
The price is ￥17,720
￥40,375 total
includes taxes & fees
Sep 8 - Sep 9
Shenandoah Valley Yurt
Private kitchen

19. 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 ￥12,516
￥25,512 total
includes taxes & fees
Sep 8 - Sep 9
RiverFront Country Home with Blue Mountain Views
Private kitchen

20. 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 ￥25,002
￥30,180 total
includes taxes & fees
Sep 7 - Sep 8
Enjoy Horses as your neighbors on 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

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"Ok"
Ricardo 1-night trip
Posted 1 hour 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:

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

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.