Madison Vacation Homes

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

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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

Madison

Tracy

HK$1,935 total

includes taxes & fees

11 Oct - 12 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

2. Charming 4-bedroom house in Madison centrally located!

Madison

Lori K.

HK$3,299 total

includes taxes & fees

13 Sept - 14 Sept

A wooden cabin with a porch, stone pathway, and outdoor seating.

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

Madison

Megan F.

HK$2,461 total

includes taxes & fees

2 Oct - 3 Oct

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

Madison

Birgit W.

HK$3,482 total

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with a central island, bar stools, and pendant lighting.

5. Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Etlan

Ikuo

HK$1,401 total

includes taxes & fees

14 Sept - 15 Sept

A two-story house with a stone facade, a front porch, and a well-maintained lawn.

6. Skyline Dr; Wineries; Small Family; Games; Skiing, Sleeps 4; Short Stays; EV+

Stanardsville

Ronald

HK$1,759 total

includes taxes & fees

13 Sept - 14 Sept

A rustic outdoor seating area with a table and chairs surrounded by a forest.

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

Etlan

HK$1,313 total

includes taxes & fees

15 Sept - 16 Sept

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

Stanardsville

Mike I.

HK$1,928 total

includes taxes & fees

13 Sept - 14 Sept

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Top Madison Hotel Reviews

English Inn of Charlottesville

10/10 Excellent

"We love this place. Clean comfortable quiet rooms, very helpful, friendly staff, and such a convenient location."

Super 8 by Wyndham Charlottesville

8/10 Good

"If you are looking for inexpensive place to put your head down for a couple of days, this motel is perfect. It is reasonably clean (no citrusy aromas but no bugs either). The TV channels are very limited, especially if you’re a sports fan. The refrigerator was broken when we arrived but after notifying front desk, we received a working one within minutes. The refrigerators are outdated big time, however clean and functional. The microwave was very clean and in working order. The bathroom was immaculate, with a working hair dryer and necessary toiletries. The desk chair was broken and almost caused an accident. The windows need a good scrub, or even replacement, but I can’t imagine that there is enough money coming in for such a project. Most importantly, since we were here in the middle of the blistering season, the air conditioning worked perfectly and made the room a great relief to come back to. I can’t say enough about the staff. They are a family working together and they make you feel like you came to visit them at their own house. Their warm and helpful attitude made any hiccup’s inconsequential."

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