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

Holiday Homes in Madison

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Madison holiday homes

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 €216
includes taxes & fees
4 Oct - 5 Oct
Historic Madison Eagle Inn
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

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 €348
includes taxes & fees
13 Sept - 14 Sept
Charming 4-bedroom house in Madison centrally located!
A wooden cabin with a porch, stone pathway, and outdoor seating.

3. 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.
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
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 €406
includes taxes & fees
17 Sept - 18 Sept
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
A rustic outdoor seating area with a table and chairs surrounded by a forest.

5. Butterfly Camp near Old Rag Mountain and Shenandoah National Park

Butterfly Camp near Old Rag Mountain and Shenandoah National Park
Etlan
The price is €155
includes taxes & fees
17 Sept - 18 Sept
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A modern kitchen with a central island, bar stools, and pendant lighting.

6. 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, (26 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is €157
includes taxes & fees
16 Sept - 17 Sept
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.

7. 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, (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 €198
includes taxes & fees
17 Sept - 18 Sept
Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+
A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

8. 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, (97 reviews)
"The house is very clean and supplied with everything you will need."
United States
Mike I.
The price is €215
includes taxes & fees
17 Sept - 18 Sept
The House in the Holla at the foot of Shenandoah National Park
A small, single-story wooden cabin with a white-framed door and a small porch.

9. 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 €200
includes taxes & fees
12 Sept - 13 Sept
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a herringbone wood floor.

10. 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 €150
includes taxes & fees
15 Sept - 16 Sept
RiverFront Country Home with Blue Mountain Views
A cozy interior with a bed, a sofa, a wooden wall, and a small table.

11. Shenandoah Valley Yurt

Shenandoah Valley Yurt
Stanley
9.8 out of 10, Exceptional, (26 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 €226
includes taxes & fees
15 Sept - 16 Sept
Shenandoah Valley Yurt
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

12. 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 €173
includes taxes & fees
13 Sept - 14 Sept
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
A kitchen with white cabinets, a granite countertop, and a tiled floor.

13. Red Brush Cottage Property

Red Brush Cottage Property
Elkton
10.0 out of 10, Exceptional, (1 review)
"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 €182
includes taxes & fees
17 Sept - 18 Sept
Red Brush Cottage Property
A living room with a fireplace, a chandelier, and a sofa.

14. The Pembroke Room in the historic Holladay House

The Pembroke Room in the historic Holladay House
Orange
9.4 out of 10, Exceptional, (3 reviews)
"The property is in the perfect location for a visit to Montpelier! Great restaurants and events are nearby. Very cozy! Great host! Expect what you would expect from a historic home. We will return."
United States
Robert
The Pembroke Room in the historic Holladay House

15. Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Sperryville
10.0 out of 10, Exceptional, (28 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is €484
includes taxes & fees
16 Sept - 17 Sept
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

16. Yellow Shutter Farmhouse Oasis

Yellow Shutter Farmhouse Oasis
Shenandoah
9.6 out of 10, Exceptional, (16 reviews)
"Nice place and hot tub was great."
United States
Rajesh
The price is €262
includes taxes & fees
17 Sept - 18 Sept
Yellow Shutter Farmhouse Oasis
A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

17. Charming 3-bdrm house in Ruckersville offering great location for your vacation

Charming 3-bdrm house in Ruckersville offering great location for your vacation
Ruckersville
10.0 out of 10, Exceptional, (12 reviews)
"Nice home, we enjoyed our stay. "
United States
Carol T.
Charming 3-bdrm house in Ruckersville offering great location for your vacation
An outdoor patio area with two wicker chairs and a small table, surrounded by a stone wall and a white fence.

18. “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, (36 reviews)
"Tracy was very welcoming and friendly. The accommodation was great."
United States
Linda N.
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
A yellow door with a 'Welcome' sign, a kitchen area with a wooden countertop and stools, and a clock on the wall.

19. Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (107 reviews)
"Beautiful home with everything we needed for our stay!"
United States
Christina P.
The price is €238
includes taxes & fees
17 Sept - 18 Sept
Historical home, walkable to many restaurants and shops.
A woman standing in a well-manicured garden with hedges and flower beds.

20. 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 €197
includes taxes & fees
13 Sept - 14 Sept
1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
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

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Outstanding stay. The food and drink at the Speakeasy were absolutely phenomenal."
Howard 4-night trip
Posted 1 hour ago
Mimslyn Inn Historic Hotels Of America

Find out more about Madison

Madison Holiday Homes information

Number of reviews
473
Accommodation
703 Holiday Homes
Lowest Price
€150
Highest Price
€484