Jamestown Settlement Rentals by Owner

8.8 (591 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Why Choose Rent By Owner for your Jamestown Settlement vacation rental?

What makes our Rentals by Owner 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 Settlement

When should you plan your Rentals by Owner stay?

To make the most of your visit, consider planning your vacation during the optimal times when the region experiences pleasant weather and fewer crowds, ensuring a relaxing and enjoyable stay in this historic destination.

Peak Season Highlights

spring
Spring (March to May)

During the springtime, the area experiences pleasant weather, making it ideal for exploring this historic destination with comfortable daytime temperatures. Visitors often enjoy fewer crowds compared to summer, providing a more relaxed experience.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
summer
Summer (June to August)

Summertime is the peak season when you can fully enjoy the region's outdoor activities and events. The warm weather attracts many travelers seeking the lively atmosphere and extended daylight hours to explore thoroughly.

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

Off-Season Highlights

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Fall (September to November)

In autumn, the area's scenic landscapes attract visitors looking for a quieter, more peaceful visit. The cooler temperatures and colorful foliage provide a perfect setting for leisurely sightseeing without the summer crowds.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
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Winter (December to February)

During the winter months, fewer tourists visit, offering a calm and intimate experience of this historic site. Despite the chill, the region's cozy ambiance and seasonal events make it a charming time for exploration.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F

Weekly Weather Forecast for Jamestown Settlement

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 a private outdoor patio or deck perfect for relaxing and dining outdoors.
  • Take advantage of shared or private swimming pools to cool off during warm days.
  • Discover beautifully maintained gardens or landscaped yards that enhance your outdoor experience.
  • Utilize dedicated grilling areas or BBQ stations for memorable cookouts in the region’s pleasant weather.
  • Make use of outdoor fire pits or fireplaces ideal for gathering with family and friends in the evenings.
  • Benefit from access to nearby walking trails or nature paths that showcase the area's scenic beauty.
  • Relish private or communal sports courts, such as tennis or basketball, available at many rentals here.
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Family Activities

  • Historical Reenactments: Witness engaging live reenactments that bring the early history of this area to life for the whole family, offering an immersive experience in colonial America.
  • Museum Tours and Exhibits: Explore interactive exhibits at the settlement, where children and adults alike can discover the stories behind this region’s rich history through hands-on activities.
  • Educational Workshops: Participate in family-friendly workshops that teach traditional skills and crafts, providing a fun learning opportunity during your visit here.
  • Scenic Outdoor Spaces: Enjoy relaxing strolls or picnics in the designated outdoor areas, perfect for unwinding after exploring the historic sites of this destination.
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Adult Activities

  • Historical Exploration Tours: Engage in guided or self-guided tours that delve into the area's rich colonial history, offering a meaningful experience for history enthusiasts.
  • Interactive Living History Exhibits: Participate in immersive exhibits that bring early American life to life, providing an authentic connection to the region’s past for adult visitors.
  • Cultural and Educational Programs: Attend special lectures, workshops, and events designed to deepen your understanding of the area's heritage and its significance in American history.
  • Shopping and Dining Experiences: Explore unique shops and dine at local eateries that showcase regional specialties, perfect for relaxing after a day of exploration in this historic destination.

Jamestown Settlement Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Hours: Arriving early or late can help you enjoy a more relaxed experience and avoid the crowds at this popular regional attraction.
  • Book Your Accommodation in Advance: Securing a rental by owner through Rent By Owner ensures you have a comfortable base close to the area's historic sites and amenities.
  • Explore Nearby Historic Sites: Take advantage of the region’s rich history by scheduling visits to other nearby landmarks and museums within the area.
  • Take Guided Tours or Educational Programs: Participating in guided experiences can enrich your understanding of this destination's cultural and historical significance.

Transportation Options

  • Car Rental Services: Renting a vehicle gives you the flexibility to explore Williamsburg and its surrounding attractions at your own pace, making it an ideal transportation choice for visitors staying near Jamestown Settlement.
  • Public Transportation: The regional bus services offer economical and convenient options for getting around the area without the need for personal vehicles, perfect for budget-conscious travelers.
  • Taxis and Ride-Sharing: Modern ride-sharing apps and taxi services provide quick and reliable transportation within Williamsburg, ensuring easy access to historic sites and local amenities.
  • Bike Rentals: For those seeking an active way to enjoy the scenery, bike rentals are available and offer an eco-friendly method to navigate this historically rich destination.

Local Customs Options

  • Respect for Colonial Traditions: You’ll find that embracing colonial customs, such as traditional dress and local historical reenactments, enriches your experience here in the region.
  • Greetings and Courtesies: Polite exchanges and courteous behavior are valued, reflecting the area's historical emphasis on community and respectful interaction.
  • Preservation of Historical Sites: Visitors are encouraged to maintain the integrity of the local sites by following guidelines and refraining from disruptive activities.
  • Participation in Local Festivals: Engaging in annual events and festivities offers a meaningful way to connect with the area's rich cultural heritage and customs.

Frequently Asked Questions About Jamestown Settlement Rentals by Owner

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 209 in the Jamestown Settlement 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 Settlement. 

3. What is the cancellation policy for a rental by owner in this area?

The cancellation policy varies depending on the individual listing. You should review the specific terms outlined in the property listing or contact the owner directly to understand the refund options and deadlines.

4. How do I ensure my booking with a private owner is secure and trustworthy?

Rent By Owner offers secure messaging and payment systems that help protect your booking. Always read reviews and confirm details directly with the owner through the platform to ensure a reliable reservation process.

5. Are there any additional fees I should be aware of when booking a rental by owner?

Additional fees such as cleaning, service charges, or taxes may apply and will be detailed in the listing. It’s best to review the full fee breakdown before confirming your reservation to avoid surprises.

6. What amenities are typically included in rentals booked directly from owners in this region?

Amenities vary by property, but many rentals include essentials like Wi-Fi, parking, and kitchen facilities. Check the specific listing for a comprehensive list of what’s included during your stay.

7. How can I contact the owner if I have questions about the rental in this destination?

You can message the owner directly through the Rent By Owner platform. This allows you to clarify details, ask questions, and receive personalized responses before booking.

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