Leon Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (25 reviews)
"Hose was excellent, great communication, helpful, answered questions, even returned items inadvertently left behind. Location was great for activities around the national park and caverns."
United States
Tracy P.
$93 nightly
The price is $104
Nov 17 - Nov 18
Total with taxes and fees
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A modern kitchen with a central island, bar stools, and pendant lighting.

2. 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, (37 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
$158 nightly
The price is $176
Nov 15 - Nov 16
Total with taxes and fees
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A room with a crib, a dining table with chairs, and a kitchen area in the background.

3. Well-appointed basement in downtown Culpeper.

Well-appointed basement in downtown Culpeper.
West Fairfax
6.6 out of 10, (4 reviews)
"There was a very strong odor. It met our needs for 1 night."
United States
Shelly M.
$223 nightly
The price is $248
Nov 11 - Nov 12
Total with taxes and fees
Well-appointed basement in downtown Culpeper.
A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

4. 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, (156 reviews)
"Picture perfect, seemless check in and the coffee and maple oatmeal were my cherry on top!"
United States
Rachel
$167 nightly
The price is $189
Dec 10 - Dec 11
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

5. 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
$231 nightly
The price is $240
Dec 1 - Dec 2
Total with taxes and fees
Historic Madison Eagle Inn
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

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

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (4 reviews)
"The home met all our family’s needs during a weekend stay for a party at nearby farm. The layout and outdoor spaces were a bonus. In fact, the view of Hawksbill Mountain from the porch while enjoying our morning coffee: priceless. And importantly easy access to Rt 29 and the town but yet secluded and bucolic."
United States
B D.
$404 nightly
The price is $450
Nov 11 - Nov 12
Total with taxes and fees
Charming 4-bedroom house in Madison centrally located!
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

7. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (68 reviews)
"Perfect little getaway."
United States
Vernon M.
$244 nightly
The price is $271
Nov 12 - Nov 13
Total with taxes and fees
The Cabin at the Lake
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

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.8 out of 10, Exceptional, (17 reviews)
"Very comfortable and clean space. Plenty of room for 1 or 2 people. Check in and out instructions were very detailed. Price was very affordable compared to the nicer hotels in town who were charging $200 to $300 a night. Kind of out in the country but its easy to get to and from town, pretty straight stretch. I was only there in the evenings and everything was very quiet and peaceful."
United States
emily
$204 nightly
The price is $215
Nov 18 - Nov 19
Total with taxes and fees
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
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

Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
Madison
9.0 out of 10, Wonderful, (2 reviews)
"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.
$412 nightly
The price is $459
Nov 11 - Nov 12
Total with taxes and fees
Lakefront Home in Madison near SNP, Wineries, Breweries, and Venues
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

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Etlan
9.4 out of 10, Exceptional, (74 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
$624 nightly
The price is $694
Nov 11 - Nov 12
Total with taxes and fees
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A wooden cabin with a porch, stone pathway, and outdoor seating.

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

Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
Madison
10.0 out of 10, Exceptional, (11 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.
$240 nightly
The price is $267
Nov 29 - Nov 30
Total with taxes and fees
Tatum's Mtn View Retreat- SAUNA-Hiking- Unit A
S'mores anyone?

12. 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, (34 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
$540 nightly
The price is $601
Nov 16 - Nov 17
Total with taxes and fees
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A house with a brick chimney, a small window, and a wooden deck.

13. Newly renovated entire guest suite in Orange County.

Newly renovated entire guest suite in Orange County.
Orange
9.8 out of 10, Exceptional, (45 reviews)
"The stay was great. Very close to all the nearby attractions and 30 minutes to skyline drive"
United States
vishal k.
$145 nightly
The price is $156
Nov 16 - Nov 17
Total with taxes and fees
Newly renovated entire guest suite in Orange County.
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

Romantic A-Frame for 2 w/ Hot Tub + Fire Pit
Unionville
10.0 out of 10, Exceptional, (1 review)
$281 nightly
The price is $300
Nov 12 - Nov 13
Total with taxes and fees
Romantic A-Frame for 2 w/ Hot Tub + Fire Pit
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

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
$560 nightly
The price is $623
Nov 12 - Nov 13
Total with taxes and fees
Walk to Old Rag | Hot Tub | Mountain Farmhouse
A garden pathway with various plants and a statue.

16. The Blenheim Suite in historic Holladay House

The Blenheim Suite in historic Holladay House
Orange
10.0 out of 10, Exceptional, (5 reviews)
"Had a weekend visit and location worked very well. Enjoyed my visit."
United States
Merrie Mac S.
$299 nightly
The price is $324
Nov 11 - Nov 12
Total with taxes and fees
The Blenheim Suite in historic Holladay House
A living room with a fireplace, a chandelier, and a sofa.

17. 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
$245 nightly
The price is $266
Nov 11 - Nov 12
Total with taxes and fees
The Pembroke Room in the historic Holladay House
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

Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy
Stanley
8.2 out of 10, Very good, (88 reviews)
"It was a beautiful cabin, exactly what we needed to get away from the city and just disconnect. If you’re not comfortable driving on mountain roads, just something to think about. Overall an amazing little getaway. "
United States
Mike B.
$331 nightly
The price is $381
Nov 17 - Nov 18
Total with taxes and fees
Beautiful Log Chalet, Hot Tub, Gas Grill, Secluded 6 wooded acres. Best privacy
A modern house with a deck, surrounded by a well-maintained lawn and trees.

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

Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
Stanley
9.2 out of 10, Wonderful, (64 reviews)
"Absolutely wonderful stay in every way!! Would definitely rent this house again!!! "
United States
Kim W.
$317 nightly
The price is $329
Nov 11 - Nov 12
Total with taxes and fees
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
A grassy field with a wooden fence, trees, and a distant building.

20. 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.
$158 nightly
The price is $170
Nov 12 - Nov 13
Total with taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
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 Leon Hotel Reviews

A modern hotel lobby with a central bar area, seating arrangements, and a coffee station.
Hampton Inn & Suites Culpeper

Hampton Inn & Suites Culpeper

Hampton Inn & Suites Culpeper
Culpeper

10/10 Excellent

Breakfast was very nice and the room was clean and comfortable.
United States
Nicholas
Reviewed October 29, 2026
Hampton Inn & Suites Culpeper

Find out more about Leon

Everything you need to know about Leon vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leon vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leon vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leon vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leon. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Leon in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Leon rentals

At Expedia, we put the best Leon vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Leon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leon vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.