Discover Your Perfect Longwood Vacation Homes

Best Vacation Homes in Longwood

Why Choose Rent By Owner for your Longwood 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 Longwood

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination can greatly enhance your experience, as seasonal weather patterns and local events in the region may influence your stay in Longwood, St. Helena.

Peak Season Highlights

spring
April to June

This period marks the warmest months in the area, making it ideal for exploring the natural beauty and enjoying outdoor activities.

Average Temperature Daytime: around 78ยฐF to 85ยฐF - Nighttime: about 65ยฐF to 70ยฐF
spring
November to February

The cooler months bring pleasant weather, perfect for experiencing local culture and scenic views without the heavy tourist crowds.

Average Temperature Daytime: approximately 70ยฐF to 75ยฐF - Nighttime: around 55ยฐF to 60ยฐF

Off-Season Highlights

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July to October

During these months, the region experiences a slight decrease in visitors, offering a quieter stay with mild weather and fewer crowds.

Average Temperature Daytime: roughly 75ยฐF to 80ยฐF - Nighttime: about 60ยฐF to 65ยฐF
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March

Early spring sees less tourist activity, providing a more relaxed atmosphere while still enjoying comfortable temperatures and tranquil surroundings.

Average Temperature Daytime: around 72ยฐF to 78ยฐF - Nighttime: approximately 58ยฐF to 62ยฐF

Weekly Weather Forecast for Longwood

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 partnerโ€™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 relaxing evenings around a private outdoor fireplace or fire pit, perfect for unwinding after exploring the region.
  • Take advantage of a spacious patio or deck area ideal for alfresco dining and entertaining with scenic views of the surrounding landscape.
  • Make the most of a well-maintained swimming pool to refresh yourself during warm days in this inviting destination.
  • Spend time in your own garden or landscaped yard, providing a peaceful outdoor setting for reading or casual gatherings.
  • Utilize outdoor grilling facilities to prepare delicious meals while enjoying the fresh air and natural surroundings.
  • Benefit from secure and dedicated parking areas that make it convenient to explore nearby attractions with ease.
  • Explore nearby walking trails or outdoor recreational areas accessible directly from your rental for an active experience in the region.
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Family Activities

  • Longwood Gardens: Explore the stunning horticultural displays and expansive outdoor gardens that provide a perfect day of family-friendly adventure and education.
  • St. Helena History Museum: Delve into the rich local history with interactive exhibits and engaging storytelling, offering insights into the area's past for visitors of all ages.
  • Visit Local Wineries: Enjoy scenic tours and kid-friendly activities at nearby wineries, where families can experience the region's renowned viticulture in a relaxed atmosphere.
  • Nature Trails and Parks: Discover the network of peaceful trails and parks around here, ideal for nature walks, picnics, and outdoor playtime with your loved ones.
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Adult Activities

  • Wine Tasting at Local Vineyards: Experience the region's renowned wine scene by visiting nearby vineyards for tastings and tours that showcase the area's rich viticultural heritage.
  • St. Helena Art Galleries: Explore the local art scene through visiting various galleries, where you can appreciate works from regional artists and find unique pieces to take home.
  • Gourmet Dining Experiences: Indulge in exceptional cuisine at fine dining establishments known for utilizing fresh, locally-sourced ingredients native to the area.
  • Historic Downtown St. Helena: Wander through charming streets lined with boutique shops, historic landmarks, and cozy cafes that reflect the area's cultural charm and history.

Longwood Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead and Localize: Research local events and seasonal activities to tailor your stay and discover unique experiences in this charming destination.
  • Explore the Region's Hidden Gems: Venture beyond typical attractions to uncover lesser-known spots that showcase the area's authentic character and beauty.
  • Choose a Prime Location: Select a vacation rental situated near key amenities or scenic areas to maximize convenience and enjoyment during your visit.
  • Engage with Local Culture: Immerse yourself in the local customs and traditions by visiting community centers or participating in regional festivals, enriching your stay here.

Transportation Options

  • St. Helena Airport: This regional airport offers convenient flights connecting you to larger hubs, making your arrival and departure straightforward when staying in the area.
  • Taxis and Ride-Sharing Services: Reliable taxi services and ride-sharing options provide flexible transportation around here, ensuring easy access to local attractions and amenities.
  • Car Rentals: Several car rental agencies are available nearby, allowing you to explore the town and its scenic surroundings at your own pace.
  • Public Transportation: Local buses operate within the region, offering an affordable way to navigate between key destinations without the need for a personal vehicle.

Local Customs Options

  • Respect for Local Heritage: Youโ€™ll find that honoring the cultural heritage is a key aspect of daily life here, with community events and traditions celebrating the area's history.
  • Traditional Crafts and Markets: Engaging with local artisans and visiting markets allows you to appreciate the regionโ€™s craftsmanship and support small-scale producers.
  • Community Hospitality: Expect warm welcomes and friendly interactions, reflecting the area's strong sense of community and openness to visitors.
  • Environmental Conservation Practices: Participating in or respecting local conservation efforts shows your appreciation for preserving the regionโ€™s natural beauty during your stay.

Frequently Asked Questions About Longwood?

What are the top vacation rentals in Longwood?

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

How many Rentbyowner vacation rentals are available in Longwood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 6 in the Longwood 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 Longwood.โ€ฏ