1. USA
  2. Delaware
  3. Wilmington
  4. Bear
  5. Rentals by Owner

Discover Your Perfect Bear Rentals by Owner

Bear Rentals by Owner

9.1 (269 Reviews)
House
Whispering Oak Mansion
  • Air Conditioner
  • Parking
  • TV
View Availability
9.8 (7 Reviews)
Apartment
Cozy loft above ink shop
  • Air Conditioner
  • Parking
  • TV
View Availability
More Top-Rated Rentals by Owner in Bear Area

Why Choose Rent By Owner for your Bear 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 Bear

When should you plan your Rentals by Owner stay?

Understanding the ideal time to visit here can help you enjoy a more relaxing and memorable vacation experience, especially when booking your rental by owner through Rent By Owner in Bear, Delaware, USA.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy the warm weather and longer daylight hours in this area, making it an ideal time for outdoor activities and exploring local surroundings.

Average Temperature Daytime: 85°F - Nighttime: 65°F
autumn
Fall (September to November)

The fall season offers cooler temperatures and vibrant foliage, perfect for experiencing the natural beauty of this destination while avoiding peak tourist crowds.

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

Off-Season Highlights

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Winter (December to February)

In the winter, the region experiences cooler temperatures and quieter streets, providing a peaceful setting for those seeking a relaxed retreat away from the bustling crowds.

Average Temperature Daytime: 45°F - Nighttime: 30°F
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Spring (March to May)

Early spring features mild temperatures and fewer visitors, making it a great time to enjoy the area’s natural landscapes at a slower pace before the summer rush begins.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Bear

How to Book Your Bear 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 Bear

More Top-Rated Rentals by Owner in Bear 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

  • Enjoy outdoor dining with a private patio or balcony, perfect for relaxing after exploring the region.
  • Take advantage of a spacious backyard or garden area, ideal for outdoor activities and family gatherings.
  • Make use of a swimming pool to cool off during warm days in this destination’s climate.
  • Benefit from access to a fire pit or outdoor fireplace for cozy evenings under the stars.
  • Explore nearby walking or biking trails that allow you to experience the natural beauty of the area.
  • Utilize outdoor furniture such as loungers and tables for enjoying the scenic surroundings.
  • Inquire if there’s a grill available for barbecues, making your stay more enjoyable and convenient.

Top Attractions Around Bear

What attractions are nearby?

In this vibrant area, you can explore a variety of outdoor activities and local attractions that showcase the region’s natural beauty and cultural charm, making your stay in Bear a memorable experience.

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Family Activities

  • Brandywine Creek State Park: Experience outdoor family fun by exploring scenic trails, picnicking, and enjoying nature at this beloved regional park.
  • Apple Scrapple Festival: Celebrate local culture with engaging activities, live entertainment, and delicious regional treats at the annual festival nearby.
  • Delaware Children's Museum: Stimulate young minds with interactive exhibits and hands-on learning experiences designed to entertain and educate in a family-friendly setting.
  • Olive Orchard Winery & Vineyards: Discover a family-oriented vineyard tour offering scenic views, tastings, and a relaxed atmosphere perfect for all ages.
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Adult Activities

  • Bear Trap Dunes Golf Club: Test your skills on well-maintained fairways at this renowned golf course, perfect for a relaxing day on the greens in the area.
  • Iron Hill Brewery & Restaurant: Enjoy a locally brewed craft beer and flavorful cuisine at this popular dining spot, ideal for unwinding after exploring the region.
  • Modern Day Art Gallery: Explore contemporary art exhibits at this engaging gallery, offering a cultural experience that enriches your stay here.
  • DE Turf Sports Complex: Participate in or watch exciting sporting events and tournaments hosted at this state-of-the-art facility in the vicinity.

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Bear Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of nearby parks and trails to enjoy the natural beauty that makes this destination a perfect outdoor retreat.
  • Book your rental early: Secure your preferred vacation home by booking in advance, especially during peak travel seasons in this region.
  • Check for local amenities: Choose a rental property that offers convenient access to shopping, dining, and entertainment options within the area.
  • Plan your transportation: Consider proximity to major roads or public transit to make exploring here more seamless during your stay.

Transportation Options

  • Regional Airport: The nearby regional airport offers convenient flights for travelers arriving from across the country or internationally, making your journey to this part of Delaware seamless.
  • Public Transit Services: Local bus and shuttle services connect you to key areas within the region, providing an affordable and reliable way to explore without a car.
  • Rental Car Agencies: Numerous rental car companies operate in the vicinity, giving you flexibility and independence to visit nearby attractions or get around easily during your stay.
  • Taxi and Rideshare Options: Taxis and rideshare services such as Uber and Lyft are readily available here, offering quick transportation solutions tailored to your schedule.

Local Customs Options

  • Local Seafood Traditions: You can experience the region's rich maritime culture through local seafood festivals and gatherings, reflecting the area's deep connection to fresh catches from nearby waters.
  • Community Events and Parades: Participating in neighborhood parades and seasonal celebrations offers a glimpse into the area's friendly spirit and strong community bonds.
  • Historic Heritage Celebrations: The region takes pride in its history, with annual heritage events where you can learn about its past and enjoy traditional music and crafts.
  • Respect for Nature and Outdoor Customs: Here, outdoor activities like fishing and hiking are cherished, embodying the locals’ appreciation for preserving the natural beauty of the area.

Frequently Asked Questions About Bear Rentals by Owner

1. What are the top Vacation Rentals in Bear?

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

2. How many Vacation Rentals are available in Bear?

Currently, the total number of properties listed by RBO in 2026 is over 74 in the Bear area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Bear. 

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

The cancellation policy varies by listing, so you should review the specific rental details and contact the owner directly for clarity on refund eligibility and deadlines.

4. How do I contact the owner of a vacation rental in Bear, Delaware?

You can reach out to the property owner through the messaging feature on the booking platform or find their contact information listed on the rental's description page for personalized inquiries.

5. Are there any amenities or features I should confirm before booking a rental in this area?

It’s recommended to review the listing carefully for amenities such as Wi-Fi, kitchen facilities, parking, and other key features that meet your needs; contacting the owner for additional questions is also advised.

6. What should I know about the check-in and check-out procedures in a rental here?

Check-in and check-out times are specified in each listing, but it’s best to confirm these details with the owner to ensure a smooth arrival and departure experience.

7. Is it safe to book a rental directly from an owner in Delaware?

Yes, booking through trusted platforms like Rent By Owner provides security features and verified listings, but always read reviews and communicate directly with the owner for a transparent and reliable experience.

More Rentals You May Like Near Bear

More Top-Rated Rentals by Owner in Bear Area