Discover Your Ideal vacation rentals in Philomont, Virginia for a memorable getaway tailored to your preferences
Discover Your Perfect Philomont Vacation Homes
Best Vacation Homes in Philomont
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Philomont Luxury Rentals
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Philomont Pet Friendly Vacation Rentals
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Philomont Large Vacation Homes
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Why Choose Rent By Owner for your Philomont Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Philomont
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, allowing you to enjoy the area's natural beauty and peaceful ambiance at its best.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences mild temperatures and blooming landscapes, making it an ideal time for outdoor activities and exploring local scenery.
Fall (September to November)
Autumn brings vibrant foliage and comfortable weather, perfect for enjoying the scenic beauty and peaceful atmosphere of this destination.
Off-Season Highlights
Winter (December to February)
In winter, cooler temperatures create a quiet getaway, appealing if you prefer a tranquil retreat away from crowds.
Summer (June to August)
Summers can be warm, but this is a less busy period when you might enjoy more flexibility in booking your vacation rentals and experiencing the region's serene environment.
Weekly Weather Forecast for Philomont
How to Book Your Philomont Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Philomont
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a fully equipped patio or barbecue area, perfect for meals under the stars.
- Relax in a private hot tub or soak in an open-air soaking tub to unwind after exploring the region.
- Take advantage of expansive gardens or landscaped yards ideal for morning yoga or leisurely strolls.
- Make use of a spacious deck or balcony offering scenic views of the surrounding countryside.
- Spend time around a cozy fire pit, perfect for gathering with family or friends during cooler evenings.
- Explore nearby walking or hiking trails that showcase the natural beauty of this destination’s outdoor landscape.
- Use outdoor sports equipment such as bikes, kayaks, or paddleboards available in some properties for active adventures in the region.
Top Attractions Around Philomont
What attractions are nearby?
Explore a variety of outdoor activities, scenic trails, and charming local attractions just minutes from your vacation rental in this peaceful region, offering the perfect setting to enjoy the natural beauty and relaxed pace of the area.

Family Activities
- Hiking at the Appalachian Trail: Explore scenic trails along the Appalachian Trail, offering a family-friendly adventure through the natural beauty of the region.
- Visiting local farms and orchards: Enjoy a day of picking fresh produce or learning about rural life at nearby farms and orchards suitable for all ages.
- Exploring community parks and outdoor spaces: Spend quality time in parks that feature playgrounds, picnic areas, and open fields perfect for family gatherings.
- Discovering historic sites and landmarks: Engage with the area's rich history by touring local landmarks that provide educational insights and fun experiences for children and adults alike.
Adult Activities
- Wine Tasting Tours: Experience the local wine scene by visiting nearby vineyards and tasting rooms that highlight the region's renowned viticulture.
- Historical Site Visits: Explore the area's rich history through guided tours or self-guided visits to notable landmarks and preserved sites.
- Nature Hiking Trails: Discover scenic hiking paths that wind through the countryside, offering stunning views and opportunities for wildlife observation.
- Farmers Markets and Artisans: Browse local farmers markets and artisan shops to enjoy fresh produce, handmade crafts, and authentic regional flavors.
Philomont Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Outdoor Adventures: Take advantage of the region’s scenic landscapes by exploring local trails and parks, ensuring you experience the natural beauty that makes this destination unique.
- Choose Your Stay Wisely: Opt for a well-reviewed vacation rental that offers privacy and comfort, making your visit here both relaxing and convenient.
- Engage with the Local Community: Connect with locals or visit nearby farmers’ markets to gain authentic insights and enrich your stay in this charming area.
- Visit During Off-Peak Seasons: Traveling during less busy times can provide a more peaceful experience and better access to all the region has to offer without the crowds.
Transportation Options
- Driving Your Car: You can conveniently navigate the region by car, with access to scenic routes and local roads leading directly to your vacation rental here.
- Public Transit: The area is connected through regional bus services, offering an affordable and eco-friendly way to explore nearby attractions and amenities.
- Airport Access: Washington Dulles International Airport is within a reasonable distance, providing international and domestic flights for your arrival and departure needs.
- Taxi and Rideshare Services: Reliable taxi, Uber, and Lyft services are available locally, ensuring easy transportation around this peaceful destination.
Local Customs Options
- Local Harvest Festivals: Embrace the region’s rich agricultural heritage by participating in seasonal harvest festivals celebrated here, which highlight the area’s farming traditions and community spirit.
- Historic Preservation Practices: Respect the local customs of preserving historic structures and landmarks that reflect the area's deep-rooted history and contribute to its charming character.
- Southern Hospitality: Experience the warm welcomes and courteous manners that are a hallmark of this destination, fostering a friendly environment for visitors exploring the area.
- Community Gardening: Engage with community-led gardening initiatives that showcase a commitment to sustainability and local food sharing within the region.
Frequently Asked Questions About Philomont?
1. What are the top vacation rentals in Philomont?
There are a lot of options in Philomont. If you plan on staying in the Philomont area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Philomont:
- Hunt Box-Antique Filled Cottage on Lowelands Farm-MiddleburgnZONR-2024-012704
- A unique mountaintop getaway overlooking Willow Croft Winery.
- Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues
- 'Anny's Farm House' in Round Hill Wine Country!
- Country Cottage on 1700’s Horse Farm/Wedding Venue
- Cozy and Beautiful Wine Country Cottage! w/Fireplace, Pond, treehouse and more!
- Historic Tip of the Hill, ca 1762, just outside of Purcellville
- Elegant Middleburg Manor with 3 Bedrooms 2 Baths
- Lovely Guest House 2.5 miles from downtown Middleburg
- Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
2. How many vacation rentals have private pools in Philomont?
There are 7 vacation rentals with private pools near Philomont. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Philomont are best for families?
If you are looking for a family-friendly vacation home in Philomont, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Philomont:
4. How many Rentbyowner vacation rentals are available in Philomont?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 96 in the Philomont area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Philomont.
5. What is the cancellation policy for vacation rentals in this region?
6. Are there any additional fees I should be aware of when booking a rental here?
7. What amenities are typically included in stays within this area?
8. How do I ensure my reservation is secure when booking a vacation home here?
9. Can I get early check-in or late check-out options for my stay?
Philomont Top Rated Vacation Rentals
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