Leon Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Leon vacation rentals

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

1. 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, bar stools, and pendant lighting.

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

Etlan

Ikuo

AED 662 total

includes taxes & fees

15 Nov - 16 Nov

A room with a crib, a dining table with chairs, and a kitchen area in the background.

3. Well-appointed basement in downtown Culpeper.

West Fairfax

Shelly M.

AED 912 total

includes taxes & fees

11 Nov - 12 Nov

A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

4. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

Rachel

AED 695 total

includes taxes & fees

9 Dec - 10 Dec

A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

5. 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.

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

Madison

B D.

AED 1,703 total

includes taxes & fees

11 Nov - 12 Nov

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

7. The Cabin at the Lake

Madison

Vernon M.

AED 1,024 total

includes taxes & fees

12 Nov - 13 Nov

A small, single-story wooden cabin with a white-framed door and a small porch.

8. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Rixeyville

emily

AED 789 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Madison

Birgit W.

AED 1,730 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Etlan

Jay R.

AED 2,549 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Madison

Megan F.

AED 993 total

includes taxes & fees

29 Nov - 30 Nov

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

Sperryville

Everett R.

AED 2,207 total

includes taxes & fees

3 Dec - 4 Dec

A house with a brick chimney, a small window, and a wooden deck.

13. Newly renovated entire guest suite in Orange County.

Orange

vishal k.

AED 571 total

includes taxes & fees

16 Nov - 17 Nov

A cabin with a wooden deck, a staircase leading to a door, and a forested background.

14. Romantic A-Frame for 2 w/ Hot Tub + Fire Pit

Unionville

AED 1,135 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Sperryville

Jeffrey C.

AED 2,355 total

includes taxes & fees

12 Nov - 13 Nov

A garden pathway with various plants and a statue.

16. The Blenheim Suite in historic Holladay House

Orange

Merrie Mac S.

AED 1,224 total

includes taxes & fees

11 Nov - 12 Nov

A living room with a fireplace, a chandelier, and a sofa.

17. The Pembroke Room in the historic Holladay House

Orange

Robert

AED 1,005 total

includes taxes & fees

11 Nov - 12 Nov

A log cabin with a large window and a wooden door.

18. Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy

Stanley

Mike B.

AED 1,400 total

includes taxes & fees

17 Nov - 18 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

11 Nov - 12 Nov

A grassy field with a wooden fence, trees, and a distant building.

20. Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Gordonsville

William J.

AED 638 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Find vacation rentals that suit your style

Top Leon Hotel Reviews

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 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

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 bar area with a granite countertop, bar stools, and shelves stocked with bottles and glasses.

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 corner of a room with a checkered floor, a metal railing, and a wall with a textured pattern.

Culpeper Center Suites

Culpeper

10/10 Excellent

Dan

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

Graves Mountain Farm & Lodges

Syria

10/10 Excellent

Derek

A buffet area with multiple food stations, a door, and a microwave in the background.

Days Inn By Wyndham Culpeper

Culpeper

10/10 Excellent

Tonna

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

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Stanardsville

10/10 Excellent

Kookju

A two-story house with a porch and a small garden area.

Hopkins Ordinary Bed Breakfast and Ale Works

Sperryville

10/10 Excellent

Anonymous traveler

An open doorway leading to a room with a dining table and chairs, a sofa, and a window.

White Moose Inn

Washington

10/10 Excellent

Jennifer

A cozy seating area with two rocking chairs and a small table, overlooking a lush garden through a large arched window.

Gay Street Inn

Washington

10/10 Excellent

Kathryn

Frequently Asked Questions

Are there vacation rentals in Leon?

Yes, you can find vacation rentals near popular points of interest in Leon, or you can go with a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Leon?

Barn Apartment on Farm Near Old Rag and Shenandoah National Park: This vacation home rental outside of Leon offers a balcony, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Leon?

While you're exploring the area, Shenandoah National Park and The Loft are a couple of picturesque spots to get outside and enjoy nature. Culpeper National Cemetery and Madison Plaza are a couple of places you'll find in the larger area.

What are vacation rentals like in Leon?

Vacation rentals are privately owned properties you can reserve for several days or more in Leon. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.

Leon Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Leon vacation rentals

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

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

3. Well-appointed basement in downtown Culpeper.

4. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

5. Historic Madison Eagle Inn

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

7. The Cabin at the Lake

8. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

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

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

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

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

13. Newly renovated entire guest suite in Orange County.

14. Romantic A-Frame for 2 w/ Hot Tub + Fire Pit

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

16. The Blenheim Suite in historic Holladay House

17. The Pembroke Room in the historic Holladay House

18. Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy

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

20. Servants' Cottage on 600 Acre Working Horse/Cattle Estate

Find vacation rentals that suit your style

Top Leon Hotel Reviews

Hampton Inn & Suites Culpeper

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Leon?

What's the top vacation rental in Leon?

What can I see and do in Leon?

What are vacation rentals like in Leon?