Rent a Ski Chalet in Upperville:【 PREMIUM 】Rent By Owner

Upperville Ski Chalets

Ski Chalet

Mountain View + Hot tub + Sauna + Yoga + Trails + Wineries + Geodesic stargazing dome

10.0

Exceptional

(2 Reviews)

2 Bedrooms 1 Bath 6 Guests 912 ft²

US $654/Night 7 Nights - US $4,581

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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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18th Century Stone Cottage minutes from historic Middleburg

Highly Rated

Cottage

18th Century Stone Cottage minutes from historic Middleburg

10.0

Exceptional

(62 Reviews)

1 Bedroom 1 Bath 2 Guests

US $399/Night 7 Nights - US $2,794

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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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Cottage

Lovely Guest House 2.5 miles from downtown Middleburg

10.0

Exceptional

(49 Reviews)

1 Bedroom 1 Bath 2 Guests

US $425/Night 7 Nights - US $2,974

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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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Cottage

Hunt Country cottage in Upperville!

10.0

Exceptional

(36 Reviews)

2 Bedrooms 1 Bath 3 Guests

US $269/Night 7 Nights - US $1,885

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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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More Top-Rated Ski Chalets in Upperville Area

Why Choose Rent By Owner for your Upperville Ski Chalets?

What makes our Ski Chalets 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 Ski Chalets stay?

Choosing the right time to vacation here can enhance your experience, as the best season for booking cozy ski chalets in this region often coincides with winter months when the area transforms into a perfect winter escape.

Peak Season Highlights

Winter (December to February)

During the winter months, you can enjoy the full experience of this destination’s snowy landscape and scenic beauty, making it an ideal time to book your ski chalets for a winter getaway.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F

Spring (March to May)

Early spring marks the end of peak season, offering pleasant weather that appeals to those seeking outdoor activities alongside skiing excursions in this region.

Average Temperature Daytime: 50°F to 65°F - Nighttime: 30°F to 45°F

Off-Season Highlights

Summer (June to August)

In the summer months, the area experiences warmer temperatures, providing a quieter period for enjoying the scenic views and planning future ski trips with less crowding.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Fall (September to November)

As the leaves change color, this destination becomes a peaceful retreat with cooler weather and fewer visitors, perfect for planning your next winter escape.

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

Weekly Weather Forecast for Upperville

How to Book Your Upperville Ski Chalets

What's our booking process?

Our platform allows you to browse a curated selection of ski chalets. 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 Ski Chalets in Upperville Area

Common Ski Chalets Amenities

What amenities can you expect?

Our Ski Chalets 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 spacious outdoor seating areas perfect for relaxing after a day on the slopes.
Take advantage of private patios or decks with stunning views of the surrounding landscape.
Make use of outdoor fire pits to gather around and share stories during cool mountain evenings.
Benefit from well-maintained gardens or landscaped yards that enhance your outdoor experience.
Access outdoor dining spaces ideal for alfresco meals with mountain scenery as your backdrop.
Utilize dedicated barbecue grills for preparing delicious meals in the fresh air.
Explore nearby walking trails or outdoor recreational areas directly accessible from your rental.

Top Attractions Around Upperville

What attractions are nearby?

While staying in this destination, you'll find a variety of outdoor activities nearby, including scenic trails and local attractions perfect for exploring the region's natural beauty and cultural heritage in Upperville, Virginia.

Family Activities

Historical Sites Tour Explore the area's rich history by visiting local landmarks that offer engaging insights into its past, perfect for family outings.
Family-Friendly Parks Spend quality time outdoors at nearby parks, where children can enjoy open spaces and safe playgrounds amidst scenic surroundings.
Local Wineries and Farms Experience farm tours and tastings suitable for families interested in learning about regional agriculture and enjoying fresh produce.
Scenic Nature Trails Discover the region's natural beauty together on walking or biking trails designed for all ages and skill levels.

Adult Activities

Wine Tasting Tours Embark on guided tastings at local vineyards to experience the region’s renowned wine culture in a relaxed setting.
Historic Site Visits Explore the region’s rich history by visiting well-preserved historic sites that showcase the area's unique heritage.
Gourmet Dining Experiences Indulge in farm-to-table dining at some of the region’s acclaimed restaurants, highlighting local flavors and culinary craftsmanship.

Upperville Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead: Book your ski chalets early to secure the best accommodations and enjoy a smooth stay in this charming area.
Explore Local Cuisine: Take time to indulge in regional dining options to fully experience the authentic flavors of the region during your visit.
Weather Awareness: Keep an eye on weather forecasts to optimize your outdoor activities and ensure your safety while exploring here.
Navigate Easily: Use local maps or GPS services to find the most convenient routes between your ski chalets and nearby attractions in this destination.

Transportation Options

Driving Renting a car provides the flexibility to explore this destination at your own pace, especially when traveling to nearby outdoor attractions or scenic spots in the area.
Public Transportation Local bus services connect key points within the region, offering an economical way to get around without the hassle of parking.
Taxi and Rideshare Services Taxis and rideshare options such as Uber or Lyft are readily available for convenient transportation especially when heading to popular dining or entertainment venues in the vicinity.
Private Shuttles Some accommodations and tour providers offer private shuttle services, ensuring a comfortable and direct route to outdoor activities or nearby cities.

Local Customs Options

Southern Hospitality Tradition: Visitors will notice the warm and welcoming demeanor that locals extend, reflecting the area's long-standing tradition of Southern hospitality.
Farmers Markets and Local Produce: Engaging in local farmers markets offers a glimpse into regional customs centered around fresh, seasonal produce and handcrafted goods.
Historic Preservation Practices: Appreciating the area's dedication to preserving its history, you'll observe respectful restoration efforts that maintain the region's authentic character.
Equestrian Culture: The local community has a rich equestrian heritage, often showcased through horseback riding traditions and related events in the area.

Frequently Asked Questions About Upperville Rental Ski Chalets

1. What are the top Ski Chalets 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 Ski Chalets in Upperville:

2. How many Ski Chalets are available in Upperville?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Upperville area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Upperville. 

3. What is the cancellation policy for booking a ski chalet in this area?

The cancellation policy varies depending on the specific listing. You should review the cancellation terms directly on the property’s page or contact the owner for detailed information before completing your reservation.

4. Are there any specific amenities included with the ski chalets here?

Amenities can differ between properties, so it’s best to check the individual listing for details on features like Wi-Fi, hot tubs, fire pits, or other conveniences to ensure they meet your needs.

5. How do I secure my booking at a ski chalet in this destination?

Booking is typically confirmed through the online platform after selecting your dates and submitting the required details. For questions about the process or special requests, reaching out directly to the property owner is recommended.

6. What should I know about the location and accessibility of ski chalets in this region?

Each property’s location provides different access options. You should review the map and description on the listing to understand proximity to ski slopes, main roads, and local attractions to plan your trip accordingly.

7. Is there a minimum stay requirement when booking a ski chalet here?

Minimum stay requirements vary by property. Be sure to check the specific listing details or contact the owner directly to confirm the length of stay needed for your preferred dates.