Discover Your Perfect Jamestown Island Vacation Homes

Jamestown Island Luxury Rentals

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9.2 (257 Reviews)
Bed & Breakfast
Williamsburg Manor B&B
  • Air Conditioner
  • Parking
  • TV
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Jamestown Island Pet Friendly Vacation Rentals

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7.8 (480 Reviews)
Resort
Kingsmill Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
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Jamestown Island Large Vacation Homes

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Why Choose Rent By Owner for your Jamestown Island 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 Island

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this destination ensures you enjoy favorable weather and fewer crowds, making your stay in vacation rentals here truly memorable.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This is the most popular time to visit, as the area's weather is warm and inviting for outdoor activities and exploring historical sites.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
autumn
Early Fall (September to October)

During this period, the region offers mild temperatures and vibrant fall foliage, making it ideal for sightseeing and enjoying the natural beauty here.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F

Off-Season Highlights

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Mid Winter (January to February)

Travelers often find fewer crowds during these months, providing a more peaceful experience while exploring the historic landscape.

Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
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Late Fall (November to December)

As the region transitions into winter, you can enjoy quieter surroundings and cooler weather, perfect for discovering the area's rich history at a relaxed pace.

Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F

Weekly Weather Forecast for Jamestown Island

How to Book Your Jamestown Island 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 Jamestown Island

More Top-Rated Vacation Rentals in Jamestown Island 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 patio or deck to relax and take in the scenic surroundings of this historic region.
  • Stay active with access to a well-maintained outdoor swimming pool, perfect for unwinding after exploring nearby attractions.
  • Benefit from spacious yards or gardens, ideal for outdoor gatherings or family playtime in the fresh air.
  • Make use of on-site barbecue grills to host outdoor cookouts amid the charming scenery of the area.
  • Take advantage of convenient parking spaces in landscaped outdoor settings, ensuring easy access to your rental.
  • Utilize outdoor seating areas designed for enjoying the tranquil views and peaceful atmosphere here.
  • Explore nearby walking trails or nature paths that provide opportunities for outdoor adventures throughout the region.

Top Attractions Around Jamestown Island

What attractions are nearby?

During your stay here, you can explore a variety of engaging activities nearby, including historical sites, scenic outdoor adventures, and cultural experiences that showcase the rich heritage of this destination.

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Family Activities

  • Historic Jamestown Settlement Tour: Discover the area's rich history with interactive exhibits and living history experiences that engage the whole family.
  • Wildlife Viewing Excursions: Enjoy spotting native birds and other wildlife in their natural habitat, offering an educational adventure for children and adults alike.
  • Storytelling and Cultural Programs: Participate in engaging storytelling sessions that bring the region's history and culture to life for visitors of all ages.
  • Parks and Nature Trails: Explore scenic walking trails and outdoor spaces perfect for family picnics and leisurely afternoons here in this historic area.
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Adult Activities

  • Historical Tours: Explore the rich history of this destination by visiting historically significant sites and learning about its colonial past.
  • Wildlife Watching: Observe native birds and other wildlife in their natural habitat along the waterfront, offering a peaceful retreat for nature enthusiasts.
  • Kayaking and Canoeing: Enjoy paddling through calm waters, providing a unique perspective of the area's scenic beauty and tranquil environment.
  • Fishing Excursions: Cast your line in designated fishing areas where you can relax and try your luck at catching local fish species.

Other Places to Stay in Jamestown Island, VA

Historic Jamestowne
Historic Jamestowne Vacation Rentals
Jamestown Settlement
Jamestown Settlement Vacation Rentals
More Places to Stay Near Jamestown Island

Jamestown Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area's rich history and natural beauty with fewer crowds, enhancing your overall experience.
  • Explore Local Historical Sites: Take advantage of the region’s historical significance by scheduling guided tours or self-guided walks that deepen your understanding of this destination's past.
  • Choose a Convenient Vacation Rental Location: Select accommodations close to key attractions and scenic spots to maximize your time exploring and minimize travel hassles here.
  • Engage in Outdoor Activities: Make the most of the area's natural environment by participating in outdoor pursuits such as walking, biking, or enjoying peaceful waterfront views near your rental.

Transportation Options

  • Car rentals: Renting a vehicle gives you the flexibility to explore this historic region at your own pace, making it an ideal transportation option for visitors staying in Jamestown Island vacation rentals.
  • Shuttle services: Local shuttle services provide convenient transportation between key sites and accommodations, ensuring a comfortable visit within the area renowned for its historic significance.
  • Public transportation: Buses and local transit options connect you to nearby attractions and amenities, offering an affordable way to navigate here without the need for private vehicles.
  • Taxis and ride-sharing: Taxis and ride-sharing apps offer quick and reliable transportation around the region, perfect for spontaneous trips or when arriving at or departing from your vacation rental.

Local Customs Options

  • Welcoming Hospitality: Guests often notice the warm and friendly demeanor of locals, reflecting the region’s rich history of community and openness.
  • Respect for Historical Sites: It’s customary to honor and preserve the area's significant historic landmarks, a practice deeply rooted in the community’s identity here in Virginia.
  • Traditional Celebrations: Participating in local festivals and events showcases the region’s appreciation for its colonial heritage and vibrant cultural traditions.
  • Environmental Conservation: The area encourages eco-friendly practices, aligning with the community’s dedication to protecting the natural beauty surrounding historic Jamestown Island.

Frequently Asked Questions About Jamestown Island?

1. What are the top vacation rentals in Jamestown Island?

There are a lot of options in Jamestown Island. If you plan on staying in the Jamestown Island 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 Island:

2. How many vacation rentals have private pools in Jamestown Island?

There are 23 vacation rentals with private pools near Jamestown Island. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Jamestown Island are best for families?

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

4. How many Rentbyowner vacation rentals are available in Jamestown Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 500 in the Jamestown Island 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 Island. 

5. What is the cancellation policy for vacation rentals in Jamestown Island?

Cancellation policies vary depending on the property owner. You should review the specific listing details or contact the host directly to understand the terms related to cancellations and refunds.

6. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning, service charges, or taxes are often included in the listing details. It’s recommended to check the complete breakdown on the property page or inquire with the host for clarity.

7. How do I find the best vacation rental that suits my needs in this destination?

You can filter options based on your preferences like amenities, price range, and guest capacity. Reading guest reviews and contacting hosts directly can also help ensure the property meets your expectations.

8. Is it possible to modify or extend my stay at a rental in the region?

Modifications or extensions depend on the property owner's policies. You should contact the host through the listing to discuss availability and request changes before finalizing your reservation.

9. What amenities are typically available at vacation rentals near the area’s attractions?

Most rentals offer essential amenities such as Wi-Fi, kitchen facilities, and parking. For specific features like pools or pet-friendly options, consult individual listings or communicate directly with the property owner.