Discover Your Perfect Kingston Vacation Homes

Best Vacation Homes in Kingston

See More Kingston Vacation Rentals

Why Choose Rent By Owner for your Kingston 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 Kingston

When should you plan your Vacation Rentals stay?

Timing your trip to this destination can greatly enhance your experience, as the region offers different attractions and weather patterns throughout the year, so consider visiting during peak seasons or quieter off-peak times to make the most of your stay.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you can enjoy the region's warm weather and longer daylight hours, ideal for exploring outdoor activities and local events.

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

This season offers pleasant temperatures and fewer crowds, making it a great time to experience the area's natural beauty and local culture.

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

Off-Season Highlights

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Mid Winter (January to February)

Visiting during the colder months allows for more peaceful getaways with less competition for accommodations, though some outdoor activities might be limited.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Late Fall (November to December)

The quiet charm of this time of year provides a cozy atmosphere perfect for relaxing in your vacation rental after the holiday season begins.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Kingston

How to Book Your Kingston 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 Kingston

More Top-Rated Vacation Rentals in Kingston 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 outdoor seating areas such as patios or decks to relax and take in the scenic surroundings.
  • Take advantage of private or community pools available at many properties in the area for a refreshing swim.
  • Make use of spacious yards or gardens ideal for outdoor dining, picnics, or family activities.
  • Explore nearby fishing spots or access to waterfronts for leisure activities along the region’s natural waterways.
  • Utilize outdoor grilling facilities to prepare meals while enjoying the pleasant weather and views.
  • Benefit from outdoor recreational amenities like basketball courts, tennis courts, or volleyball areas when available.
  • Experience the region’s natural beauty through easy access to walking trails, biking paths, or nature preserves nearby.

Top Attractions Around Kingston

What attractions are nearby?

While staying here, you can explore nearby boating, fishing, and outdoor recreation opportunities that highlight the natural beauty of the region.

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Family Activities

  • Marion Station Community Park: Enjoy a relaxing day outdoors with family picnics and playground fun at this scenic park nearby.
  • Smith Island Cultural Center: Discover the rich local history and traditional crafts that highlight the area’s unique heritage, engaging for all ages.
  • Fishing on the Chesapeake Bay: Experience memorable fishing adventures in the bay, perfect for families seeking outdoor recreation close to their rental accommodations.
  • Wildlife Watching at Deal Island Wildlife Management Area: Observe native birds and other wildlife in their natural habitat, offering educational opportunities right here in the region.
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Adult Activities

  • Fishing and Boating on the Pocomoke River: You can enjoy peaceful days of fishing or rent a boat to explore the scenic waters that surround this part of Maryland.
  • Bird Watching at Assateague State Park: The area is renowned for its diverse bird species, making it an ideal spot for nature enthusiasts seeking a tranquil escape.
  • Golfing at local courses: Tee off at nearby golf courses that offer challenging holes and beautiful views, perfect for a relaxing day on the greens.
  • Visiting Chesapeake Bay Maritime Museum: Discover the region’s rich maritime history through interactive exhibits and historic ships, providing an engaging experience here in Maryland.

Kingston Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Shops: Take time to discover the area's charming eateries and boutiques, which can enhance your stay by offering authentic regional experiences.
  • Plan Outdoor Activities: Make the most of the surrounding natural beauty by engaging in outdoor pursuits such as fishing, boating, or nature walks available nearby.
  • Visit Nearby Attractions: Research and visit popular attractions in the region to deepen your understanding and appreciation of this destination's unique culture and history.
  • Communicate with Your Host: Connect with your vacation rental host beforehand for tailored recommendations and tips that will help you navigate and enjoy your time here fully.

Transportation Options

  • Kingston Transportation Services: You can easily access reliable local transportation options within the area to explore the region comfortably.
  • Public Transit Systems: The regional bus services provide convenient and economical travel throughout this destination and nearby locations.
  • Rental Car Agencies: Renting a car here offers flexibility, allowing you to visit attractions at your own pace in the surrounding region.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options are readily available for quick and hassle-free transportation around Kingston and its neighboring communities.

Local Customs Options

  • Local Seafood Cuisine: In this area, enjoying fresh Maryland seafood is a cherished tradition that reflects the region's rich maritime heritage.
  • Community Events and Festivals: Participating in seasonal festivals offers insight into local customs and brings you closer to the friendly community here.
  • Historical Respect: Visitors often observe a deep respect for the area's history, which is celebrated through preservation efforts and local storytelling.
  • Casual and Friendly Hospitality: The region is known for its welcoming atmosphere where residents pride themselves on providing warm, relaxed interactions for guests.

Frequently Asked Questions About Kingston?

1. What are the top vacation rentals in Kingston?

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

2. How many vacation rentals have private pools in Kingston?

There are 2 vacation rentals with private pools near Kingston. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Kingston are best for families?

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

4. How many Rentbyowner vacation rentals are available in Kingston?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 93 in the Kingston 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 Kingston. 

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

Cancellation policies vary by property, so it’s important to review the specific terms listed on each rental page or contact the owner directly for detailed information.

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

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. Be sure to read the full description or reach out to the property owner for clarity before booking.

7. How do I verify the safety and cleanliness standards of the vacation rentals in this region?

Properties often include information about their cleanliness protocols and safety features in their listing descriptions. You can also contact the owner directly to inquire about specific health and safety measures implemented.

8. What amenities are generally available in vacation rentals around here?

Most listings provide a comprehensive list of amenities offered, which may include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Checking each listing will give you a clear understanding of what is included during your stay.

9. How do I ensure my booking is secure and protected when reserving a vacation rental in this destination?

Reservations made through a reputable platform are protected by secure payment systems. It’s recommended to communicate through the official booking channels and review the platform’s policies to ensure your transaction is safe.