1. USA
  2. Maryland
  3. Frederick
  4. Middleburg
  5. Rentals by Owner

Discover Your Perfect Middleburg Rentals by Owner

Middleburg Rentals by Owner

More Top-Rated Rentals by Owner in Middleburg Area

Why Choose Rent By Owner for your Middleburg vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Middleburg

When should you plan your Rentals by Owner stay?

Choosing the optimal time to visit here allows you to enjoy the region's serene beauty and make the most of your rental by owner experience in Middleburg, Keymar, Maryland, USA.

Peak Season Highlights

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Spring (March to May)

During spring, the area experiences mild temperatures and lush scenery, making it an ideal time for outdoor activities and exploring local attractions.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
autumn
Fall (September to November)

Autumn offers vibrant foliage and cooler weather, perfect for scenic drives and enjoying the region’s natural beauty while avoiding peak crowds.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Summer (June to August)

Summertime brings warmer weather, but it can also be busier due to holiday travelers; early mornings and late evenings are ideal for visiting here comfortably.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
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Winter (December to February)

Winter is quieter with cooler temperatures, providing a peaceful retreat and a chance to enjoy the area's serene atmosphere without the summer crowds.

Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F

Weekly Weather Forecast for Middleburg

How to Book Your Middleburg vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Middleburg

More Top-Rated Rentals by Owner in Middleburg Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 a spacious outdoor patio or deck perfect for relaxing or entertaining amidst the scenic surroundings.
  • Take advantage of well-maintained gardens or landscaped yards that add to the outdoor charm of your stay.
  • Make the most of an outdoor dining area, ideal for enjoying meals while soaking up the natural beauty of the region.
  • Experience the convenience of outdoor grilling facilities to prepare delicious meals during your visit.
  • Utilize a private swimming pool or hot tub for added relaxation in the fresh air.
  • Benefit from ample parking spaces with outdoor parking options suited for multiple vehicles.
  • Explore nearby walking trails or nature paths directly accessible from the rental property, allowing you to connect with this area's natural landscape.

Top Attractions Around Middleburg

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities, explore scenic nature trails, and experience local events that highlight the area's rich cultural heritage, making your stay truly memorable.

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Family Activities

  • Black Walnut Winery Tasting Room: You can enjoy family-friendly wine tastings and scenic views at this charming winery in the area, perfect for a relaxing day together.
  • Virginia Gold Cup Races: Experience thrilling horse racing events that offer entertainment for the whole family during the region’s annual celebrations.
  • Middleburg Community Center: Engage in community events, classes, or recreational activities suitable for children and adults alike within this welcoming local hub.
  • Country Trails Riding Center: Discover horseback riding lessons and trail rides that provide an enjoyable outdoor experience for your family in this scenic destination.
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Adult Activities

  • Wine Tasting Tours: Explore the nearby vineyards and indulge in wine tasting experiences that showcase the region’s renowned local wineries.
  • Historic Estate Visits: Discover the area’s rich history by touring historic estates and learning about the region’s cultural heritage.
  • Equestrian Activities: Enjoy horseback riding through scenic trails, offering a peaceful way to experience the countryside here.
  • Golfing Adventures: Play a round of golf at championship courses set amidst picturesque landscapes, perfect for a relaxing day on the links.

Middleburg Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and wine experiences: Take time to indulge in the region's renowned culinary scene, savoring fresh regional produce and local wines to enhance your stay.
  • Plan outdoor activities wisely: Make the most of the area's scenic landscapes by scheduling outdoor adventures such as hiking or horseback riding during optimal weather conditions.
  • Connect with community events: Check out local gatherings or festivals happening nearby to immerse yourself in the area's culture and meet fellow travelers.
  • Utilize your rental’s amenities: Maximize comfort and convenience by taking full advantage of the unique features and facilities offered by your Rent By Owner rental here.

Transportation Options

  • Personal Vehicle: Renting or using your own car offers the most flexibility for exploring the scenic surrounds of Middleburg and the nearby region.
  • Local Taxi Services: Reliable taxi options are available in the area, providing convenient transportation to local attractions and amenities.
  • Car Rentals: Several rental agencies operate nearby, giving you access to a vehicle suited for navigating the picturesque countryside and rural roads.
  • Public Transit: Limited but available bus services connect key points in the region, ideal for budget-conscious travelers looking to move around here economically.

Local Customs Options

  • Southern Hospitality: The locals here take pride in their welcoming attitude, often greeting visitors with warmth and friendliness when exploring the area.
  • Local Agriculture Traditions: Celebrating agricultural roots, you might notice regional farmers participating in seasonal fairs and markets that showcase local produce.
  • Historic Preservation: Respect for history is evident through well-maintained landmarks and preservation efforts that highlight the region's rich past.
  • Community Festivals: Throughout the year, community-oriented festivals reflect the area's cultural heritage and provide authentic local experiences for visitors.

Frequently Asked Questions About Middleburg Rentals by Owner

1. What are the top vacation rentals in Middleburg?

There are a lot of options in Middleburg. If you plan on staying in the Middleburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middleburg:

2. How many Rentbyowner vacation rentals are available in Middleburg?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 55 in the Middleburg 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 Middleburg. 

3. What is the cancellation policy for rentals by owner in this area?

Cancellation policies vary depending on the individual listing. You should review the specific rental's policy on the listing page or contact the owner directly to understand the terms and any applicable fees.

4. How do I confirm the availability of a vacation rental by owner in this destination?

Availability can be confirmed by checking the calendar on the rental listing or by reaching out directly to the owner for real-time updates and to ensure your desired dates are open.

5. Are there any additional fees I should expect when booking a rental in this region?

Additional fees such as cleaning, service charges, or security deposits are specified in the listing details. It's recommended to review these before completing your reservation or contact the owner for clarification.

6. What amenities are typically included in rentals by owner here?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. For specific features, refer to the detailed listing description or ask the owner directly.

7. How do I contact the property owner if I have questions during my stay?

You can communicate with the owner through the messaging platform provided on the booking site. For urgent concerns, look for contact details listed in the rental information or message the owner directly.

More Rentals You May Like Near Middleburg

More Top-Rated Rentals by Owner in Middleburg Area