A forest path with a mulch-covered trail, surrounded by various flowering plants and trees.

Madison Vacation Rentals

Q: What's the top vacation rental in Madison?

Mountainside Villas at Massanutten by Tripforth : Visitors like this Madison vacation home rental. It 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.

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Dates

November 2026

December 2026

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Our top choices for Madison vacation rentals

A hallway with a wooden bench, a red door, and a framed picture on the wall.

1. Historic Madison Eagle Inn

Madison

Tracy

AED 881 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Madison

B D.

A spacious kitchen with modern appliances, a dining area with a large table, and a cozy living area with a sofa and coffee table.

3. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

Madison

Birgit W.

AED 1,730 total

includes taxes & fees

12 Nov - 13 Nov

A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

4. The Cabin at the Lake

Madison

Vernon M.

AED 1,024 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Madison

Megan F.

AED 993 total

includes taxes & fees

29 Nov - 30 Nov

A glass enclosure with a view of a forest interior, including a bed and various plants.

6. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

Rachel

AED 695 total

includes taxes & fees

10 Dec - 11 Dec

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

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

Etlan

Ikuo

AED 701 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Stanardsville

Jason

AED 674 total

includes taxes & fees

15 Nov - 16 Nov

A cabin with a wooden deck, two chairs, a red door, and a window.

9. Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Etlan

Maria N.

AED 380 total

includes taxes & fees

17 Nov - 18 Nov

A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a cat sitting by the counter.

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

Ruckersville

Carol T.

AED 1,649 total

includes taxes & fees

12 Nov - 13 Nov

A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

11. Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Etlan

Jay R.

AED 2,688 total

includes taxes & fees

12 Nov - 13 Nov

A wooden deck with Adirondack chairs and a table, surrounded by dense forest and a stream.

12. The House in the Holla at the foot of Shenandoah National Park

Stanardsville

Victor V.

AED 861 total

includes taxes & fees

15 Nov - 16 Nov

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

Sperryville

Everett R.

AED 2,207 total

includes taxes & fees

16 Nov - 17 Nov

A cabin with a large window overlooking a flowing river, a wooden interior, and a small table with a patterned tablecloth.

14. Log Cabin on the River

Stanardsville

Melanie B.

AED 973 total

includes taxes & fees

17 Nov - 18 Nov

A wooden staircase leading to a deck with a railing, a potted plant, and a metal chair.

15. Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

Stanardsville

samantha b.

AED 653 total

includes taxes & fees

16 Nov - 17 Nov

A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

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

Sperryville

Jeffrey C.

AED 2,355 total

includes taxes & fees

12 Nov - 13 Nov

A forested area with a fire pit and Adirondack chairs.

17. Moonfire Farm Shenandoah region cozy getaway

Barboursville

Matt

AED 705 total

includes taxes & fees

12 Nov - 13 Nov

A living room with a stone fireplace, black leather sofa, and a flat-screen TV mounted on the wall.

18. Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

Gordonsville

B S.

AED 1,541 total

includes taxes & fees

12 Nov - 13 Nov

A modern house with a deck, surrounded by a well-maintained lawn and trees.

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

Stanley

Kim W.

AED 1,208 total

includes taxes & fees

12 Nov - 13 Nov

A grassy field with four wooden Adirondack chairs arranged in a semi-circle.

20. Elegant Chalet on a 600-Acre Horse and Cattle Ranch

Gordonsville

Todd R.

AED 926 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Find vacation rentals that suit your style

Top Madison Hotel Reviews

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

10/10 Excellent

Kookju

A modern hotel lobby with a central bar area, seating arrangements, and a coffee station.

Hampton Inn & Suites Culpeper

Culpeper

10/10 Excellent

Nicholas

A swimming pool with multiple lanes, lounge chairs, and a table with chairs.

Holiday Inn Express Hotel & Suites Culpeper by IHG

Culpeper

10/10 Excellent

Erin

A Holiday Inn Express hotel with a brick facade, a covered entrance, and a well-lit exterior.

Holiday Inn Express & Suites Charlottesville - Ruckersville by IHG

Barboursville

10/10 Excellent

traveler

A multi-story hotel with a brick facade, large windows, and a central entrance with a glass door.

Microtel Inn & Suites by Wyndham Culpeper

Culpeper

10/10 Excellent

Alexandria

Baymont by Wyndham Culpeper

Culpeper

10/10 Excellent

My family was very pleasantly surprised with our stay. We arrived late Friday night to a very friendly desk clerk who took care of us quickly and professionally. Room was very nice and comfortable. We were staying here for its proximity to a swim meet in the area. The next morning we awoke and went down to Peppers for what we were expecting to be a no thrills breakfast but were we surprised; a very delicious plentiful buffet that was much more than we could have ever expected. Thank you for the...

donald

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance.

Inn at Willow Grove

Orange

10/10 Excellent

Anonymous traveler

A lodge with a large dining area and a fire pit in the foreground.

Graves Mountain Farm & Lodges

Syria

10/10 Excellent

Derek

A conference room with multiple tables and chairs, a projector screen, and a carpeted floor.

Days Inn By Wyndham Culpeper

Culpeper

10/10 Excellent

Tonna

A hotel room with two beds, a sofa, a coffee table, and framed pictures on the wall.

Comfort Inn & Suites Charlottesville Hollymead Town Center

Hollymead

10/10 Excellent

This is a brand new property and very clean. We had a larger suite with the small pull out sofa. Overall we are a family of five and I always notice the size of a room and this one was on the larger size. If you have younger children they would have room to play on the floor. The breakfast was typical but stocked, clean, and decent. My teens ate without complaints. The staff was friendly and accommodating. We left a piece of jewelry behind, realized it about an hour later and called and...

Billie

Mayhurst Inn

Orange

10/10 Excellent

Casey is a remarkable host, delivering with her family, a very high quality experience! No amenity was overlooked. The property is in excellent condition; the grounds and setting, interesting and historical; the breakfast scrumptious and memorable; and the nearby downtown city of Orange afforded very good restaurant access. Simply, the best B & B experience we have had the pleasure to enjoy, thanks to Casey's and fam's effort!

Edward

A hallway with a wooden floor, a potted plant, and a door on the right.

Culpeper Center Suites

Culpeper

10/10 Excellent

Dan

An outdoor patio area with a fire pit, seating, and a pergola structure.

Staybridge Suites Charlottesville Airport by IHG

Hollymead

10/10 Excellent

James

A building with a brick facade and white columns, a brick pathway, and a door with a wreath.

The Estate at Meander

Locust Dale

10/10 Excellent

Anonymous traveler

A courtyard with a brick pathway, surrounded by neatly trimmed hedges and trees, leading to a building with a tiled roof and brick walls.

English Inn of Charlottesville

The Meadows

10/10 Excellent

Tina

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: Visitors like this Madison vacation home rental. It 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.

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.

Madison Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Madison vacation rentals

1. Historic Madison Eagle Inn

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

3. Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues

4. The Cabin at the Lake

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

6. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

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

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

9. Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

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

11. Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

12. The House in the Holla at the foot of Shenandoah National Park

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

14. Log Cabin on the River

15. Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP

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

17. Moonfire Farm Shenandoah region cozy getaway

18. Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm

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

20. Elegant Chalet on a 600-Acre Horse and Cattle Ranch

Find vacation rentals that suit your style

Top Madison Hotel Reviews

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Madison?

What's the top vacation rental in Madison?

How many vacation rentals will I find in Madison?

What can I see and do in Madison?

What are vacation rentals like in Madison?