1. USA
  2. Maryland
  3. Kennedyville
  4. Rentals by Owner

Discover Your Perfect Kennedyville Rentals by Owner

Kennedyville Rentals by Owner

10.0 (89 Reviews)
Apartment
Eastern Shore Get Away
  • Air Conditioner
  • Parking
  • TV
View Availability
More Top-Rated Rentals by Owner in Kennedyville Area

Why Choose Rent By Owner for your Kennedyville vacation rental?

What makes our Rentals by Owner special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Kennedyville

When should you plan your Rentals by Owner stay?

Choosing the ideal time to visit the area ensures you experience the region's unique charm at its best, making your stay through Rent By Owner in Kennedyville, Maryland, truly memorable and tailored to your preferences.

Peak Season Highlights

spring
Spring (March to May)

During this time, you can enjoy the region’s mild weather and blooming landscapes, making it ideal for outdoor activities.

Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F
summer
Summer (June to August)

Summer offers warm temperatures perfect for relaxing in your rental by owner property and enjoying longer daylight hours.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F

Off-Season Highlights

image
Fall (September to November)

Visit in the fall to experience the area’s vibrant foliage and cooler temperatures, providing a peaceful retreat.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
image
Winter (December to February)

Winter months are quieter, offering a cozy atmosphere with less crowds, ideal for those seeking tranquility and off-season rates.

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

Weekly Weather Forecast for Kennedyville

How to Book Your Kennedyville vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Kennedyville

More Top-Rated Rentals by Owner in Kennedyville Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

  • You can enjoy a private outdoor space with a patio or deck to relax and unwind amidst the scenic surroundings.
  • Many rentals feature a spacious yard, perfect for outdoor games or a peaceful walk in the fresh air.
  • Look for properties with barbecue grills, making it easy to host outdoor meals during your stay.
  • Expect to find outdoor dining areas that allow you to savor meals while taking in the region's natural beauty.
  • Some accommodations include access to a swimming pool, offering a refreshing way to cool off on warm days.
  • Outdoor fire pits are available at select rentals, providing cozy evenings under the stars.
  • Enjoy well-maintained gardens or landscaped grounds that enhance your overall outdoor experience here.

Top Attractions Around Kennedyville

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities and scenic experiences that highlight the natural beauty nearby, making your stay both relaxing and memorable.

image
image

Family Activities

  • Kent County Recreation Park: Enjoy a family picnic and outdoor games at this scenic park, perfect for exploring the natural beauty of the area.
  • The Chesapeake Bay Maritime Museum: Discover local maritime history through engaging exhibits and boat tours that captivate visitors of all ages here in the region.
  • Peaceful Green Space & Nature Trails: Take leisurely strolls or bike rides along well-maintained trails that offer a peaceful retreat suitable for family adventures in the area.
  • Local Farmers Markets: Sample fresh, regional produce and handmade goods at nearby markets, providing a fun cultural experience for the whole family.
image

Adult Activities

  • Fishing at the Chesapeake Bay: Experience tranquil fishing opportunities along the bay, offering a relaxing day immersed in nature's beauty.
  • Bird Watching in the Local Wetlands: Discover diverse bird species in the area’s wetlands, perfect for nature enthusiasts seeking peaceful observer moments.
  • Exploring Local Farms and Markets: Visit nearby farms and markets to enjoy fresh produce and learn about regional agricultural traditions.
  • Hiking and Nature Walks: Take advantage of scenic trails that wind through the region, ideal for outdoor lovers wanting to embrace the area's natural landscape.

Kennedyville Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region's scenic parks and waterways to enjoy kayaking, fishing, or nature walks right from your rental.
  • Connect with hosts for insider tips: Reach out to your rental owner to get personalized recommendations on hidden gems and the best local spots to visit.
  • Plan your visit during peak seasons: Booking ahead for popular times ensures you experience the area’s vibrant atmosphere and avoid last-minute availability issues.
  • Utilize nearby transportation options: Familiarize yourself with local transit or car rental services to conveniently explore the surrounding region from your accommodation.

Transportation Options

  • Car Rentals: Opt for nearby car rental services to easily explore the region and access your rental property with convenience.
  • Taxi Services: Reliable taxi companies operate in the area, providing a quick and hassle-free transportation option for your stay here.
  • Public Transit: Local bus services connect key points in the region, offering an affordable way to travel without the need for personal transportation.
  • Ride-Sharing: Popular ride-sharing apps provide convenient transportation options tailored to your schedule while enjoying the comfort of local rides here.

Local Customs Options

  • Crab Feast Traditions: Participating in local crab feasts is a cherished custom here, offering a taste of the area's rich maritime heritage.
  • Old-fashioned Seafood Festivals: Attending seasonal seafood festivals allows you to experience the region's deep-rooted connection to fresh, local catches.
  • Waterfront Celebrations: Engaging in events along the coast reflects the community’s appreciation for its scenic waterways and maritime culture.
  • Historic Preservation Events: Visiting special gatherings dedicated to preserving the area's history provides insight into this destination’s unique past.

Frequently Asked Questions About Kennedyville Rentals by Owner

1. What are the top vacation rentals in Kennedyville?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 88 in the Kennedyville 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 Kennedyville. 

3. How do I find the cancellation policy for a rental by owner in the area?

You can review the cancellation policy directly on the listing page before booking. If you have specific questions, contacting the property owner through the platform ensures clarity.

4. What amenities are typically available in rentals by owner in this destination?

Most rentals by owner in the region offer essential amenities such as Wi-Fi, parking, and fully equipped kitchens. Detailed information about amenities is listed on each property’s page.

5. Is there a secure way to communicate with the property owner during my stay?

Yes, the platform provides a secure messaging system to contact owners directly. It’s recommended to use this feature for all communication related to your booking.

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

Additional fees such as cleaning or service charges may apply and are detailed in the listing. Reading the full fee breakdown helps you understand the total cost upfront.

7. What is the process for confirming my reservation in this area?

Reservations are confirmed once you complete the booking and payment process outlined on the listing page. Confirmations are sent via email, and you can contact the owner for any special arrangements.

More Rentals You May Like Near Kennedyville

10.0 (2 Reviews)
House
Anchors Away!
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Kennedyville Area