Discover Your Perfect Kent County Vacation Homes

Best Vacation Homes in Kent County

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10.0 (56 Reviews)
Bed & Breakfast
Inn at Huntingfield Creek
  • Air Conditioner
  • Parking
  • Pool
View Availability
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Kent County Luxury Rentals

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Find More Kent County Villas, Resorts, & Rentals on BedroomVillas

Why Choose Rent By Owner for your Kent County 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 Kent County

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, allowing you to enjoy the region's unique charm and outdoor activities at their best.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the region experiences warm weather and blooming scenery, making it ideal for outdoor activities and exploring local attractions.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
summer
Mid to Late Summer (July to August)

The peak summer months bring lively local events and longer daylight hours, perfect for enjoying coastal activities and scenic views.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F

Off-Season Highlights

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Fall (September to October)

As the area transitions into autumn, you’ll find cooler temperatures and fewer crowds, offering a more tranquil experience while still enjoying pleasant weather.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
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Winter (December to February)

During winter, the region offers a quiet and cozy atmosphere with mild to chilly temperatures, ideal for those seeking a peaceful retreat away from the busy season.

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

Weekly Weather Forecast for Kent County

How to Book Your Kent County 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 Kent County

More Top-Rated Vacation Rentals in Kent County 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 dining spaces perfect for alfresco meals amidst scenic views of the region.
  • Relax in private or shared gardens that showcase the natural beauty of the area.
  • Take advantage of spacious decks or patios ideal for unwinding after a day exploring the destination.
  • Make use of outdoor grilling facilities to prepare delicious meals with local ingredients.
  • Benefit from access to waterfront amenities, including private docks or beaches, if available in the area.
  • Utilize outdoor fire pits or fireplaces for cozy gatherings under the stars.
  • Explore well-maintained yards or grounds suitable for outdoor activities and relaxation.

Top Attractions Around Kent County

What attractions are nearby?

In this charming region, you can explore scenic outdoor activities, visit local historic sites, or enjoy waterfront dining just a short drive from your vacation rental.

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Family Activities

  • Kent County Nature Trails: Explore scenic trails suited for family hikes and outdoor adventures, offering a chance to enjoy the region’s natural beauty.
  • Chesapeake Bay Maritime Museum: Discover maritime history through engaging exhibits and hands-on activities that captivate children and adults alike in this coastal area.
  • Eastern Neck National Wildlife Refuge: Experience wildlife viewing and birdwatching opportunities within this protected sanctuary, ideal for family educational outings.
  • Knox Point Park: Relax with your loved ones at this waterfront park, perfect for picnics, fishing, and soaking in stunning views of the bay while enjoying family fun activities.
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Adult Activities

  • Explore the Chesapeake Bay Maritime Museum: Dive into this area's rich maritime history and enjoy interactive exhibits that bring the region’s seafaring traditions to life.
  • Enjoy kayaking and paddleboarding on the Chesapeake Bay: Embark on a water adventure along the scenic waterways, ideal for experiencing the natural beauty of the region firsthand.
  • Visit local wineries and tasting rooms: Discover the area's vibrant wine scene with tastings that highlight the unique flavors produced here in Maryland’s countryside.
  • Participate in birdwatching and nature walks at conservation areas: Experience the region's diverse wildlife and tranquil landscapes as you explore its protected natural habitats.

Other Places to Stay in Kent County, MD

Great Oak Landing
Great Oak Landing Vacation Rentals
Georgetown
Georgetown Vacation Rentals
Betterton Beach
Betterton Beach Vacation Rentals
Betterton
Betterton Vacation Rentals
Still Pond
Still Pond Vacation Rentals
Crow Farm and Vineyard
Crow Farm and Vineyard Vacation Rentals
Kennedyville
Kennedyville Vacation Rentals
Rock Hall
Rock Hall Vacation Rentals
Galena
Galena Vacation Rentals
Tolchester Beach
Tolchester Beach Vacation Rentals
Chestertown
Chestertown Vacation Rentals
Millington
Millington Vacation Rentals
More Places to Stay Near Kent County

Kent County Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Local Waterfronts: Take advantage of the area's picturesque waterways to enjoy boating, fishing, or simply relaxing by the river, making your stay more memorable.
  • Visit the Historic Downtown: Spend time exploring charming shops and eateries in the heart of this destination, immersing yourself in its rich local culture.
  • Plan Outdoor Adventures: Utilize nearby parks and nature reserves for hiking, birdwatching, or picnicking, enhancing your outdoor experience here.
  • Discover Seasonal Events: Check the local calendar for festivals and events that showcase the region's unique traditions and community spirit during your visit.

Transportation Options

  • Kent County Transit System: This regional bus service offers convenient transportation options within the area, making it easy to explore local attractions and amenities.
  • Amtrak Train Service: The nearby Amtrak stations provide reliable rail connections for travel to and from other major cities along the East Coast.
  • Local Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available here, offering flexible transportation directly from your vacation rental.
  • Private Car Rentals: Several car rental agencies operate in the vicinity, giving you the freedom to explore the region at your own pace during your stay.

Local Customs Options

  • Crab Feasting Traditions: You’ll find that enjoying Chesapeake Bay blue crabs is a cherished custom here, often shared during gatherings to celebrate local culinary heritage.
  • Maritime Greeting Etiquette: When visiting the area’s waterfront communities, expect friendly waves and nods as part of the coastal hospitality that welcomes all visitors.
  • Historic Preservation Practices: Respect for the region’s rich history means observing local customs of maintaining and honoring historic sites and buildings.
  • Seasonal Festivals: Participating in seasonal events such as summer boat parades and harvest celebrations allows you to experience authentic local traditions firsthand.

Frequently Asked Questions About Kent County?

1. What are the top vacation rentals in Kent County?

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

2. How many vacation rentals have private pools in Kent County?

There are 3 vacation rentals with private pools near Kent County. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Kent County are best for families?

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

4. How many Rentbyowner vacation rentals are available in Kent County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 171 in the Kent County 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 Kent County. 

5. What is the cancellation policy for vacation rentals in Kent County, Maryland?

Cancellation policies vary by listing, so you should review the specific property's terms before booking. Details are available on each listing page or can be clarified by contacting the property owner directly.

6. How do I find a vacation rental that allows pets in this area?

Many properties in Kent County, Maryland, specify pet allowances in their listings. You can filter your search to include pet-friendly options and reach out to hosts for confirmation or additional questions.

7. Are there any minimum stay requirements for booking here?

Minimum stay requirements depend on the individual property and the time of year. Details are listed on each vacation rental’s page, or you may inquire directly with the host for extended stays or special arrangements.

8. What amenities are typically included in vacation rentals in this region?

Most properties offer essential amenities such as Wi-Fi, full kitchens, and outdoor spaces. However, specific features like pools or boat docks may vary; always check the listing details or contact the owner for clarity.

9. How can I ensure my booking in the area is secure and trustworthy?

Choose listings with verified profiles and positive reviews. Communicate through the platform’s messaging system and review the host’s profile and ratings to ensure a reliable and seamless booking experience.