Upperville Accommodations

Cabin

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

10.0

Exceptional

(21 Reviews)

4 Bedrooms 2 Baths 8 Guests

US $555/Night 7 Nights - US $3,888

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Historical Paris Cabin on Farm w/Fire Pit!

House

Historical Paris Cabin on Farm w/Fire Pit!

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 7 Guests 2497.23 ft²

US $401/Night 7 Nights - US $2,805

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House

Grand 9BR Provenance Manor Ideal for Gatherings

9 Bedrooms 6 Baths 16 Guests

US $1,693/Night 7 Nights - US $11,850

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Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Highly Rated

House

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

10.0

Exceptional

(76 Reviews)

3 Bedrooms 2 Baths 6 Guests

US $470/Night 7 Nights - US $3,290

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Villa

Elegant Paris Manor w/Private Pool!

6 Bedrooms 7 Baths 13 Guests 9999.67 ft²

US $1,910/Night 7 Nights - US $13,370

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House

Cozy Country Getaway in the Heart of Upperville

10.0

Exceptional

(21 Reviews)

2 Bedrooms 2 Baths 5 Guests

US $347/Night 7 Nights - US $2,432

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Nature Escape - Pond, Dock, Fire Pit, Trails

Price Dropped

House

Nature Escape - Pond, Dock, Fire Pit, Trails

5 Bedrooms 5 Baths 12 Guests 2777.09 ft²

US $635/Night 7 Nights - US $4,448

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House

5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.

10.0

Exceptional

(6 Reviews)

1 Bedroom 1 Bath 2 Guests

US $181/Night 7 Nights - US $1,267

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House

Nature Escape Pond Dock Fire Pit Trails

1 Bedroom 1 Bath 12 Guests 258.33 ft²

US $828/Night 7 Nights - US $5,796

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House

Guest House at Mt Independence

10.0

Exceptional

(4 Reviews)

2 Bedrooms 1 Bath 6 Guests 2002 ft²

US $364/Night 7 Nights - US $2,550

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New

House

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

1 Bedroom 2 Baths 8 Guests 204.51 ft²

US $436/Night 7 Nights - US $3,055

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Apartment

Farm Suite at Valley View Farm

9.4

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 2 Guests

US $224/Night 7 Nights - US $1,569

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More Top-Rated Accommodations in Upperville Area

Why Choose Rent By Owner for your Upperville Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Upperville

When should you plan your Accommodations stay?

Choosing the optimal time to visit here can greatly enhance your experience, as engaging with the local seasons and climate ensures you enjoy the region’s unique charm at its best when planning your stay through RentByOwner.com.

Peak Season Highlights

Spring (March to May)

During spring, the region experiences pleasant weather and blooming landscapes, making it an ideal time for exploring the area's natural beauty and outdoor activities.

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

Fall (September to November)

Autumn offers vibrant foliage and comfortable temperatures, perfect for enjoying outdoor pursuits and experiencing the region’s scenic charm.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

Winter (December to February)

Winter tends to be quieter with cooler weather, providing a peaceful atmosphere and potential savings on accommodations while enjoying this serene destination.

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

Summer (June to August)

While summer brings warm weather and lively outdoor events, it is also the busiest time, so early booking ensures you secure the best accommodations here.

Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F

Weekly Weather Forecast for Upperville

How to Book Your Upperville Accommodations

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

Book Online

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

Explore and book the perfect rental in Upperville

More Top-Rated Accommodations in Upperville Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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 private outdoor patio or deck perfect for relaxing and dining amidst the scenic surroundings.
Take advantage of spacious yards or gardens ideal for outdoor activities or leisurely strolls.
Make use of an outdoor swimming pool to cool off during warm summer days in the region.
Utilize well-maintained fire pits or outdoor fireplaces for cozy evenings under the stars.
Benefit from access to walking trails or nature paths surrounding the property, perfect for exploration.
Relax in a landscaped garden area designed to enhance your stay with natural beauty.
Take advantage of outdoor dining setups, such as picnic tables or BBQ grills, for memorable meals al fresco.

Top Attractions Around Upperville

What attractions are nearby?

In this charming part of Virginia, you can enjoy a variety of outdoor activities, explore scenic parks, and visit local historic sites that showcase the area's rich heritage, making your stay here both relaxing and culturally enriching.

Family Activities

Morven Park Explore expansive gardens, enjoy family-friendly walking trails, and visit the historic mansion for a full day of outdoor activities suitable for all ages.
Blue Ridge Center for Environmental Stewardship Engage in educational nature programs, trail walks, and wildlife observation to foster an appreciation for local ecosystems.
Hunt Country Stable Tours Experience scenic horseback riding adventures that provide a fun and memorable way for families to connect with the region’s equestrian heritage.
Catoctin Creek Distillery's Family Events Participate in family-oriented tours and tasting sessions designed to introduce younger visitors to local craft traditions in a welcoming environment.

Adult Activities

Wine Tasting Tours Explore the renowned vineyards and enjoy guided wine tastings that showcase the region’s celebrated viticulture.
Historic Horse Country Discover the area's rich equestrian heritage with visits to equestrian farms and participating in horseback riding experiences.
Gourmet Dining Experiences Indulge in local culinary delights at fine dining establishments that highlight regional flavors and farm-to-table ingredients.
Scenic Nature Trails Take advantage of the picturesque landscapes by hiking or walking along trails that reveal the natural beauty of this destination.

Upperville Travel Tips

How Can You Make the Most of Your Stay?

Explore local dining and wineries: Take advantage of the area's renowned culinary scene and wine tasting opportunities to immerse yourself in the regional flavors during your stay.
Plan outdoor activities: Make the most of the scenic countryside by engaging in outdoor pursuits such as horseback riding, hiking, or leisurely strolls through picturesque landscapes.
Visit nearby historic sites: Discover the rich history of the region by exploring nearby heritage sites that offer insight into its cultural significance.
Choose central accommodations: Book properties that are conveniently located to key attractions and amenities to maximize your comfort and exploration time here.

Transportation Options

Driving You can easily explore the area by car, with several major highways connecting here to surrounding regions, making it a convenient transportation option for your trip.
Public Transit Regional bus services offer reliable transportation within this destination and neighboring towns, providing an affordable way to get around without a car.
Taxis and Rideshare Services Taxis and popular rideshare options are readily available, offering flexible and direct transportation throughout the region.
Rental Cars Numerous rental car agencies operate in nearby cities, allowing you to rent a vehicle and enjoy the freedom to explore at your own pace.

Local Customs Options

Southern Hospitality: Visitors often notice the warm and welcoming attitude that embodies the local customs, making your stay here more inviting and comfortable.
Horse-Centered Traditions: Equine culture is deeply rooted in the region, influencing local events and community gatherings centered around horseback riding and breeding.
Traditional music and seasonal festivals play a key role in celebrating the area's rich heritage and fostering community spirit.
Historic Preservation: Respect for history is evident through the careful maintenance of historic sites and architecture that reflect the area's timeless charm.

Frequently Asked Questions about Upperville Accommodations

1. What are the top Accommodations in Upperville?

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

2. How many Accommodations are available in Upperville?

Currently, the total number of properties listed by RBO in 2026 is over 42 in the Upperville area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Upperville. 

3. What is the cancellation policy for bookings in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details before booking. Many accommodations offer flexible options, but some may have stricter terms. For precise information, please consult the listing or contact the host directly.

4. Are there any hidden fees or additional costs when booking here?

Additional fees such as cleaning charges, service fees, or taxes may apply depending on the property. All costs should be clearly outlined during the booking process, but reviewing the full fee breakdown on each listing helps ensure transparency before finalizing your reservation.

5. How do I know if the accommodations are available for my travel dates?

Availability depends on current bookings and the specific property’s schedule. You can easily check real-time availability by entering your travel dates on the listing page. If your preferred dates are unavailable, consider reaching out to the host for possible alternatives.

6. Can I get assistance if I encounter issues during my stay?

Yes, most hosts offer support for guests during their stay. Details about how to contact the host or support services are typically provided in the listing. For urgent concerns, contacting the host directly through the platform ensures a prompt response.

7. What amenities are included with the accommodations in this destination?

Amenities vary by property but often include essentials like Wi-Fi, parking, heating or air conditioning, and kitchen facilities. To verify specific amenities, review the property listing thoroughly or contact the owner for additional details before booking.