1. USA
  2. Virginia
  3. Middleburg
  4. Rentals by Owner

Discover Your Perfect Middleburg Rentals by Owner

Middleburg Rentals by Owner

|
9.6 (42 Reviews)
Resort
Salamander Resort and Spa
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
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?

Determining the ideal time to vacation here can enhance your experience, as the best seasons often coincide with pleasant weather and seasonal events that highlight the region’s charm.

Peak Season Highlights

spring
Spring (March to May)

During spring, you can enjoy the vibrant atmosphere and lush landscapes in this region, making it an ideal time for outdoor activities and exploring local scenery.

Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
autumn
Fall (September to November)

Autumn offers colorful foliage and a charming ambiance, perfect for discovering the area's scenic beauty and participating in seasonal events.

Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F

Off-Season Highlights

image
Summer (June to August)

The summer months see fewer visitors, providing a quieter experience while enjoying warm weather and longer daylight hours for outdoor exploration.

Average Temperature Daytime: 80-85°F - Nighttime: 60-65°F
image
Winter (December to February)

In winter, the area tends to be less crowded, offering a peaceful retreat with potential for cozy indoor activities amidst the cooler temperatures.

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 terrace, perfect for relaxing and dining al fresco in the fresh air.
  • Take advantage of well-maintained gardens or landscaped yards that showcase the region’s natural beauty.
  • Make use of a private swimming pool or hot tub to unwind after exploring the area's scenic surroundings.
  • Benefit from outdoor grilling facilities to enjoy barbecues with friends or family in the open air.
  • Experience the convenience of on-site parking options tailored for easy access during your stay.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars in this charming destination.
  • Discover dedicated spaces for outdoor recreation, such as bocce courts or tennis courts, for active leisure amidst the region's picturesque setting.

Top Attractions Around Middleburg

What attractions are nearby?

In this charming region, you'll find a variety of outdoor activities and local attractions to enjoy, making your stay truly memorable.

image
image

Family Activities

  • Visit the Middleburg Museum of Historic Horses and Hounds: Engage your family with interactive exhibits that showcase the region's equestrian heritage, perfect for a fun day of learning and exploration.
  • Explore the nearby Oatlands Historic House and Gardens: Stroll through stunning gardens and tour historic mansion grounds to immerse yourselves in the area's rich history and natural beauty.
  • Enjoy outdoor adventures at local parks: Spend quality time together hiking, picnicking, or exploring scenic trails in the region’s family-friendly parks and outdoor recreation areas.
  • Discover Middleburg’s charming downtown shops and cafes: Wander through quaint streets filled with boutique stores and family-friendly eateries, making for a delightful and relaxed outing here.
image

Adult Activities

  • Wine Tasting Tours: Explore the region's renowned vineyards and enjoy guided tastings that highlight the area's rich winemaking heritage.
  • Horseback Riding Experiences: Discover scenic trails on horseback, immersing yourself in the countryside's natural beauty and equestrian traditions.
  • Gourmet Dining: Indulge in farm-to-table cuisine at local restaurants known for showcasing the area's fresh, regional ingredients.
  • Historic District Walks: Stroll through charming streets filled with preserved architecture and learn about the area's storied past from knowledgeable guides.

Other Places to Stay in Middleburg, VA

Chrysalis Vineyards
Explore 71 Properties
Dover
Explore 68 Properties
Cana Vineyards and Winery
Explore 68 Properties
Glenwood Park
Explore 33 Properties
Tudor Day Spa
Explore 31 Properties
Trowbridge-Lewis Galleries
Explore 30 Properties
Red Fox Fine Art
Explore 30 Properties
The Byrne Gallery
Explore 30 Properties
The Sporting Gallery
Explore 30 Properties
National Sporting Library & Museum
Explore 29 Properties
Piedmont Vineyards and Winery
Explore 28 Properties
Greenhill Winery & Vineyards
Explore 26 Properties
More Places to Stay Near Middleburg

Middleburg Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the regional calendar to align your visit with local festivals or markets, enhancing your experience here.
  • Explore Unique Rental Options: Opt for a rental by owner that offers a genuine home-away-from-home atmosphere in this charming area.
  • Discover Scenic Routes: Take advantage of the picturesque countryside by planning drives around the region's most scenic routes during your stay.
  • Support Local Businesses: Use your time here to visit boutique shops and eateries, contributing to the community’s vibrant local economy.

Transportation Options

  • Car Rentals: Renting a car gives you the flexibility to explore this scenic region at your own pace, especially when booking through trusted providers near Middleburg's charming surroundings.
  • Taxi Services: Reliable taxi services are available here for convenient door-to-door transportation, ideal for quick trips within the area or to nearby attractions.
  • Rideshare Options: Rideshare companies operate in the region, offering a seamless and cost-effective way to travel between your rental and local destinations.
  • Public Transportation: Local bus routes provide an economical option for getting around this part of Virginia, connecting major points of interest with ease and affordability.

Local Customs Options

  • Horse Country Hospitality: Embrace the region’s deep-rooted equestrian culture by observing local customs related to horse shows and riding traditions during your stay.
  • Farmers' Market Etiquette: Support local producers by engaging in friendly customs at farmers' markets, where fresh regional produce and handmade goods are celebrated.
  • Historic Dress and Events: Participate respectfully in the area’s historical reenactments and festivals that highlight the rich colonial and Civil War heritage.
  • Respect the quiet rural lifestyle by observing local manners, such as polite greetings and consideration for the countryside ambiance.

Middleburg Rentals by Owner Frequently Asked Questions

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 26 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 rental properties in Middleburg, Virginia?

Cancellation policies vary by listing, so it's important to review the specific terms outlined in the property description or contact the owner directly before booking.

4. How do I ensure the rental I book by owner in the area meets my needs?

You can verify amenities, check the detailed description, and communicate with the owner to confirm that the property aligns with your requirements before finalizing your reservation.

5. Are there any additional fees associated with booking a vacation rental here?

Additional fees such as cleaning charges or service fees are often listed during the booking process. It’s recommended to review all fee details on the listing page or ask the owner directly.

6. What is the best way to contact the owner of a rental in this region if I have questions?

You can typically reach out through the messaging platform provided on the booking site to ask questions or clarify details before confirming your reservation.

7. Is there a minimum stay requirement for rentals in this part of Virginia?

Minimum stay requirements vary depending on the property; please check the specific listing details or contact the owner to confirm the duration needed for your booking.

More Rentals You May Like Near Middleburg

More Top-Rated Rentals by Owner in Middleburg Area