Discover Your Perfect Highland Vacation Homes

Best Vacation Homes in Highland

Highland Luxury Rentals

Why Choose Rent By Owner for your Highland 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 Highland

When should you plan your Vacation Rentals stay?

Timing your trip to this charming destination can greatly enhance your experience, as the best seasons for visiting often align with pleasant weather and local events that showcase the area's unique appeal.

Peak Season Highlights

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Spring (March to May)

During the spring months, the area experiences mild temperatures and blooming landscapes, making it an ideal time to explore local surroundings and enjoy outdoor activities.

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

Autumn brings colorful foliage and comfortable weather, providing a picturesque setting for your stay in this destination.

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

Off-Season Highlights

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Summer (June to August)

Summer can be hot and humid, but it also offers longer days for sightseeing and outdoor excursions at this region’s most vibrant time of year.

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

While winter is quieter, the cooler temperatures create a cozy atmosphere, perfect for relaxing indoors or enjoying off-season discounts on vacation rentals.

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

Weekly Weather Forecast for Highland

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.

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 outdoor dining with a well-equipped patio or picnic area to relax and unwind during your stay.
  • Take advantage of private gardens or landscaped yards that provide a peaceful retreat in the countryside.
  • Make the most of spacious decks or balconies offering scenic views of the surrounding region.
  • Stay active with access to walking trails, perfect for exploring the natural beauty of this destination.
  • Benefit from outdoor fire pits or fireplaces ideal for cozy evenings under the stars.
  • Utilize outdoor recreational facilities such as basketball courts or volleyball areas, great for group fun.
  • Relax by the outdoor swimming pool, which is a popular feature for enjoying warm days here.
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Family Activities

  • Highland Nature Trail: Explore scenic walking paths through lush landscapes, offering an engaging outdoor experience for the whole family in this charming part of Dublin.
  • Virginia Children's Museum: Discover interactive exhibits and hands-on activities designed to inspire creativity and learning for young visitors in the region.
  • Local Farmers Market: Visit the area's vibrant market to enjoy fresh produce, local crafts, and family-friendly outings that support community artisans.
  • Community Park & Playground: Spend quality time at a local park featuring spacious play areas, perfect for picnics and outdoor fun during your stay here.
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Adult Activities

  • Wine Tasting Tours: Experience the region's renowned wineries and savor local wines in guided tastings that highlight the area's rich viticulture.
  • Historical Site Visits: Discover the area's history by exploring notable landmarks and museums that offer insight into its cultural heritage.
  • Outdoor Recreation: Enjoy outdoor activities such as hiking, biking, or picnicking amidst scenic landscapes that define the region's natural beauty.
  • Local Dining Experiences: Indulge in diverse culinary offerings at nearby restaurants that showcase regional flavors and farm-to-table freshness.

Highland Travel Tips

How Can You Make the Most of Your Stay?

  • Research Local Attractions: Discover nearby outdoor activities and cultural sites to enrich your stay in this charming destination.
  • Choose the Right Accommodation: Opt for vacation rentals that offer convenient amenities to enhance comfort during your visit here.
  • Plan Your Transportation: Familiarize yourself with local transit options or consider renting a vehicle to explore the region at your own pace.
  • Engage with the Community: Take time to connect with local businesses and residents, making your experience more authentic and memorable in this part of Virginia.

Transportation Options

  • Personal Vehicles: Renting a car offers the flexibility to explore the scenic region surrounding Highland, Dublin, Virginia, at your own pace, making it ideal for reaching outdoor attractions and local dining spots.
  • Airport Shuttles and Taxis: Convenient airport transfer services are available for easy arrivals and departures from nearby airports, ensuring a smooth start and end to your stay in the area.
  • Public Transit: Local bus services provide an affordable and eco-friendly way to navigate the region, connecting you to key points of interest without the hassle of parking.
  • Bike Rentals: For a leisurely exploration of the area's charming neighborhoods and natural surroundings, bike rentals are an excellent transportation choice, offering both convenience and exercise.

Local Customs Options

  • Southern Hospitality: You will notice a welcoming atmosphere and friendly interactions that reflect the region's warm and courteous spirit.
  • Participating in local celebrations often involves enjoying traditional music and community gatherings that highlight Highland’s cultural heritage.
  • Cuisine Etiquette: Dining customs typically emphasize hospitality, with shared meals and an appreciation for locally sourced ingredients prominent here.
  • Respect for Nature: The area values outdoor traditions, encouraging visitors to engage respectfully with its scenic landscapes and natural resources.

Frequently Asked Questions About Highland?

2. Which vacation homes in Highland are best for families?

If you are looking for a family-friendly vacation home in Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland:

3. How many Rentbyowner vacation rentals are available in Highland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 34 in the Highland 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 Highland. 

4. What is the cancellation policy for vacation rentals in Highland, Dublin, Virginia?

Cancellation policies vary depending on the specific property. You should review the cancellation terms listed on each property’s page or contact the owner directly to understand the details and any potential fees.

5. Are there any restrictions on booking dates for Highland vacation rentals during peak seasons?

Availability during peak seasons may be limited. It’s recommended to check the calendar on the listing and communicate with the property owner to confirm your desired dates.

6. How do I ensure the vacation rental I book in this area meets my amenities and comfort needs?

Property descriptions include detailed amenities and features. Reading the listing carefully and reaching out to the host can help you verify that the vacation rental meets your preferences.

7. What security deposit or additional fees should I expect when booking here?

Additional fees such as security deposits, cleaning fees, or service charges are outlined in the listing details. Confirm these with the property owner before finalizing your reservation.

8. How do I contact the property owner if I have questions before booking a vacation rental in this region?

You can contact the owner directly through the messaging system on the listing platform. Reviewing the owner’s contact information and message history can facilitate clear communication prior to booking.