Discover Your Perfect Jamestown Vacation Homes

Why Choose Rent By Owner for your Jamestown 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 Jamestown

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can greatly enhance your experience, so consider the local climate and seasonal trends when planning your stay here in Jamestown, St. Helena, to ensure your vacation rental offers the perfect escape during your preferred period.

Peak Season Highlights

spring
April to June

During the spring months, you will experience warm weather ideal for exploring the region's natural beauty and historic sites. This is the most popular time to visit, so booking your vacation rentals early is recommended.

Average Temperature Daytime: 22°C to 26°C - Nighttime: 16°C to 19°C
spring
September to November

Autumn offers comfortable temperatures and a quieter atmosphere, making it an excellent period to enjoy the area's outdoor activities and scenic views. Vacation rentals tend to fill up quickly during this peak season.

Average Temperature Daytime: 20°C to 24°C - Nighttime: 14°C to 17°C

Off-Season Highlights

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December to February

The winter months bring cooler temperatures to the region, providing a peaceful escape for those seeking solitude and reduced crowds. It's a good time to find more affordable vacation rental options here.

Average Temperature Daytime: 17°C to 20°C - Nighttime: 12°C to 14°C
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July to August

Mid-summer typically sees fewer visitors, offering a laid-back experience with pleasant weather for exploring at your own pace. Booking early ensures access to the best vacation rentals here during this quieter season.

Average Temperature Daytime: 21°C to 25°C - Nighttime: 15°C to 18°C

Weekly Weather Forecast for Jamestown

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 spaces to savor meals while taking in the scenic surroundings of this destination.
  • Relax on spacious decks or patios that provide perfect settings for unwinding after a day of exploring.
  • Make use of private gardens or landscaped yards ideal for outdoor activities or simply enjoying the fresh air.
  • Take advantage of outdoor grills for barbecues, adding a delicious touch to your stay here.
  • Utilize dedicated outdoor seating areas designed for gatherings and relaxing with family or friends.
  • Benefit from access to well-maintained lawns or open spaces suitable for recreational games or picnics.
  • Experience the charm of outdoor fire pits or fireplaces, perfect for cozy evenings under the stars.
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Family Activities

  • Jamestown Museum: Explore the local history and culture through interactive exhibits that provide insight into the area's rich heritage.
  • Longwood House and Gardens: Discover the beauty of meticulously maintained gardens and learn about the historical significance of this former plantation estate.
  • James Bay Nature Reserve: Enjoy family-friendly walks and observe diverse wildlife within this scenic reserve, perfect for outdoor adventures in the region.
  • The St. Helena Distillery Tour: Experience a guided tour of the distillery to learn about the island's famous rum production process, ideal for a family interested in local craftsmanship.
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Adult Activities

  • Historical Walking Tours: Discover the rich history of this destination through guided tours that take you through its iconic landmarks and stories.
  • Hiking along the Coastal Trails: Explore scenic routes offering breathtaking ocean views, perfect for outdoor enthusiasts seeking adventure in the region.
  • Local Art Galleries and Studios: Immerse yourself in the area's vibrant art scene by visiting galleries showcasing local talent and craftsmanship.
  • Sea Angling Excursions: Experience the thrill of deep-sea fishing off here’s coast, a popular activity for those looking to enjoy the region's maritime environment.

Jamestown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Make the most of your stay by trying out the region’s authentic cuisine at local eateries to truly experience the area’s unique flavor.
  • Plan Nature Activities: Take advantage of the natural beauty surrounding here with outdoor activities that showcase the scenic landscapes and tranquil environment.
  • Visit Historic Sites: Dive into the area's rich history by scheduling visits to notable historic locations, enriching your understanding of the destination.
  • Choose a Prime Location for Your Accommodation: Select your vacation rental in a central area to maximize convenience and access to the region’s key attractions and amenities.

Transportation Options

  • Local Bus Service: You can utilize the regional bus service to conveniently explore Jamestown and the surrounding areas within St. Helena.
  • Private Taxis and Ride-Sharing: Reliable taxi and ride-sharing services are available for personalized transportation throughout this destination.
  • Chartered Boat Tours: For scenic views and unique access, consider booking a chartered boat tour around the area’s coastline.
  • Rental Cars: Renting a vehicle provides you with flexible travel options to discover all corners of this region at your own pace.

Local Customs Options

  • Respect for the Local Customs: When visiting here, you'll notice a strong emphasis on respecting traditional practices and community values that are deeply rooted in this destination's history.
  • Greeting Etiquette: It is customary to greet locals with a warm smile and polite gestures, reflecting the friendly and welcoming nature of the region.
  • Dress Codes for Religious Sites: Modest attire is preferred when visiting religious or cultural sites within the area, so be sure to dress appropriately to show respect to local traditions.
  • Celebration of Local Festivals: Participating in or observing local festivals provides a meaningful way to engage with the area's heritage and meet residents embracing their customs.

Jamestown Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Jamestown?

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

2. How many Rentbyowner vacation rentals are available in Jamestown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 9 in the Jamestown 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 Jamestown. 

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

Cancellation policies can vary depending on the individual listing. You should review the specific property's cancellation terms carefully before booking or contact the owner directly for clarification.

4. Are there any additional fees I should be aware of when booking in this destination?

Additional fees such as cleaning charges, service fees, or security deposits may apply. Details are provided in each listing, so it's best to read the description thoroughly or reach out to the host for exact information.

5. How can I ensure my reservation is secure and reliable?

Reservations made through trusted platforms include secure payment options and verified listings. Always confirm the host’s reviews and ratings to ensure a trustworthy stay here.

6. What amenities are typically included with holiday rentals in this region?

Amenities can differ between properties, but many offer essential features like Wi-Fi, kitchens, and outdoor spaces. For a complete list, review the property details or ask the owner directly.

7. What is the check-in and check-out process for stays in this location?

Check-in and check-out procedures vary by property. Specific instructions are provided in the listing, and you can contact the owner if you need further assistance or special arrangements.