Discover Your Perfect Chrysalis Vineyards Vacation Homes

Best Vacation Homes in Chrysalis Vineyards

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9.8 (40 Reviews)
Resort
Salamander Resort and Spa
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.4 (127 Reviews)
Bed & Breakfast
Inn at Evergreen
  • Air Conditioner
  • Parking
  • Pool
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9.6 (389 Reviews)
Hotel
The Red Fox Inn & Tavern
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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9.4 (28 Reviews)
House
Bull Run Mountain Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Chrysalis Vineyards Vacation Rental Homes?

What makes our Vacation Rentals 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 Chrysalis Vineyards

When should you plan your Vacation Rentals stay?

Finding the ideal time to visit here ensures you experience the region’s beauty and tranquility at its best, making your stay in Chrysalis Vineyards even more memorable.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, this destination awakens with vibrant blooms and mild temperatures, making it an ideal time to explore local vineyards and scenic countryside.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

Autumn offers stunning foliage and harvest festivities, attracting visitors who wish to experience the region’s rich viticulture and charming ambiance.

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

Off-Season Highlights

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Winter (December to February)

The quieter winter period allows for peaceful retreats and cozy accommodations, perfect for those looking to enjoy the area without the crowds.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Summer (June to August)

While summer can bring warmer weather suitable for outdoor activities, it is also the least busy season, providing you with more privacy during your stay.

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

Weekly Weather Forecast for Chrysalis Vineyards

How to Book Your Chrysalis Vineyards Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Chrysalis Vineyards

More Top-Rated Vacation Rentals in Chrysalis Vineyards Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 seating area perfect for relaxing amidst scenic views of the surrounding vineyards.
  • Take advantage of a spacious yard ideal for outdoor dining, picnics, or gatherings with friends and family.
  • Access a well-maintained garden where you can stroll and appreciate the region’s lush landscape.
  • Utilize outdoor grilling facilities to prepare delicious meals while enjoying the fresh air.
  • Make use of designated parking areas that provide easy access to your rental home and outdoor amenities.
  • Benefit from scenic walking trails nearby, offering opportunities for outdoor exploration in the area.
  • Relax in the outdoor lounge chairs or hammocks set up for unwinding after a day of exploring this destination.

Top Attractions Around Chrysalis Vineyards

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities, historic sites, and local wineries, all perfect for enhancing your stay at nearby vacation rentals in Middleburg, Virginia.

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Family Activities

  • Family Winery Tours: Experience engaging wine tastings and guided tours designed to introduce children and adults to the region’s renowned vineyards in a family-friendly setting.
  • Pony Rides and Farm Activities: Enjoy outdoor adventures like pony rides and other farm-focused activities that are perfect for young explorers staying nearby.
  • Scenic Nature Walks: Discover picturesque walking trails through the countryside, offering a peaceful way for families to connect with nature and take in the area's natural beauty.
  • Picnic Opportunities: Pack a leisurely picnic to enjoy in designated areas around the region, making the most of your stay here with loved ones.
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Adult Activities

  • Wine Tasting Tours: Experience guided tastings at the vineyard, where you can sample some of the region's finest wines crafted from local grapes.
  • Vineyard Walks and Tours: Explore the scenic grounds on a leisurely walk, taking in the rolling vineyards and learning about the winemaking process directly from the experts.
  • Private Events and Tastings: Attend exclusive wine tastings or private events hosted amidst the picturesque setting, perfect for adults seeking a refined experience.
  • Wine and Food Pairing Experiences: Enhance your visit with culinary pairings that beautifully complement the region's signature wines, providing a delightful gastronomic adventure.

Chrysalis Vineyards Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during quieter times allows you to enjoy the tranquility of this destination and experience the region's charm without crowds.
  • Explore Local Wineries and Tastings: Take advantage of nearby vineyards to immerse yourself in the area's renowned wine culture and enhance your stay here.
  • Discover Scenic Drives and Nature Trails: Use the region’s picturesque landscapes for memorable drives or hikes, enriching your vacation with natural beauty.
  • Book Your Accommodation Early: Secure your preferred vacation rentals well in advance to ensure availability and better rates during peak seasons here.

Transportation Options

  • Private Car Services: You can hire a private car or chauffeur service to conveniently explore the region surrounding Chrysalis Vineyards, ensuring a comfortable and personalized journey.
  • Rental Cars: Renting a car locally provides flexibility to visit nearby attractions in Middleburg and beyond at your own pace, making it an ideal option for this scenic area.
  • Public Transportation: Although limited, regional bus services offer an affordable way to travel between key destinations in the area without the hassle of parking.
  • Bicycle Rentals: For a more leisurely experience, consider renting bicycles to enjoy the picturesque landscapes and vineyard views here at your own pace.

Local Customs Options

  • Wine Tasting Etiquette: Locals here often observe a respectful and leisurely approach to wine tasting, emphasizing appreciation over haste at many of the region’s renowned vineyards.
  • Horse Country Traditions: The area has a deep equestrian heritage, where visitors typically participate in or observe traditional horse shows and understand the importance of riding customs.
  • Historical Preservation: Respect for the region's historic sites is common, with residents valuing preservation efforts and visitors encouraged to honor these traditions when exploring local landmarks.
  • Farmers’ Market Practices: Supporting local agriculture is a cherished custom, often involving engaging directly with vendors and appreciating farm-fresh produce during visits to nearby markets.

Frequently Asked Questions About Chrysalis Vineyards?

1. What are the top vacation rentals in Chrysalis Vineyards?

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

2. How many Rentbyowner vacation rentals are available in Chrysalis Vineyards?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 75 in the Chrysalis Vineyards 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 Chrysalis Vineyards. 

3. What is the cancellation policy for booking a vacation rental in this destination?

Cancellation policies vary by listing, so it’s important to review the specific terms on the property page or contact the owner directly. This ensures you understand any fees or restrictions associated with changes or cancellations.

4. How do I inquire about availability and book my stay in the region?

Availability can be checked directly on the listing, and you can proceed with booking by following the prompts. For additional questions or special requests, reaching out to the property owner helps ensure your plans are confirmed seamlessly.

5. Are there any house rules I should be aware of before booking?

Each property may have its own set of house rules specified in the listing. Be sure to read these carefully to ensure your stay complies with the owner's expectations and any local regulations.

6. Is there a minimum stay requirement when reserving here?

Minimum stay requirements vary per property, and details are listed on each vacation rental page. If you have specific dates in mind, contacting the owner can also provide clarification.

7. What amenities are typically included in vacation rentals in this area?

Most vacation rentals offer amenities such as Wi-Fi, kitchen facilities, and parking. For a detailed list of what's included, review the property description or reach out to the owner to confirm that it meets your needs.

Best Vacation Homes in Chrysalis Vineyards