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  2. Delaware
  3. Wilmington
  4. Bear
  5. Vacation Rentals with Pools

Bear Vacation Rentals with Pools

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7.2 (456 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
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7.0 (285 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Bear Vacation Rentals with Pools?

What makes our Vacation Rentals with Pools 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 Vacation Rentals with Pools stay?

Choosing the optimal time to vacation here ensures you can enjoy the region’s pleasant climate and make the most of your stay in properties offering relaxing pools, providing a seamless experience tailored to your preferred season for visiting this destination.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences warm weather ideal for enjoying your rentals with pools and outdoor activities.

Average Temperature Daytime: 85°F - 90°F - Nighttime: 65°F - 70°F
autumn
Fall (September to November)

Early fall offers pleasant temperatures and vibrant scenery, making it an excellent time for relaxing stays with pools before the winter season begins.

Average Temperature Daytime: 75°F - 80°F - Nighttime: 55°F - 60°F

Off-Season Highlights

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Winter (December to February)

The cooler winter months bring lower temperatures, so you might prefer indoor amenities; however, some rentals offer cozy pools for year-round enjoyment.

Average Temperature Daytime: 40°F - 50°F - Nighttime: 25°F - 35°F
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Spring (March to May)

As the region transitions into warmer weather, spring can be quieter, offering a peaceful retreat with opportunities to enjoy your rentals with pools in a tranquil setting.

Average Temperature Daytime: 60°F - 70°F - Nighttime: 40°F - 50°F

Weekly Weather Forecast for Bear

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.

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 swimming pool to relax and unwind during your stay.
  • Take advantage of spacious patios or decks ideal for outdoor dining and entertaining.
  • Benefit from lush, landscaped gardens that create a peaceful outdoor environment.
  • Make the most of outdoor grilling areas perfect for family barbecues.
  • Relax in cozy outdoor seating areas designed for enjoying the fresh air.
  • Access nearby walking trails and outdoor recreation spots within the region.
  • Experience tranquil outdoor spaces that enhance your overall vacation experience in this area.
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Family Activities

  • Carousel County Park Enjoy a family picnic and outdoor activities at this scenic park, perfect for relaxing after a day of exploring the region.
  • Bear Library Foster a love for reading and participate in engaging children’s programs at this community library located nearby.
  • Trail Walking and Biking Paths Discover the numerous trails suitable for walking and biking that wind through the area's natural landscape, ideal for outdoor family adventures.
  • Community Events and Festivals Experience local culture by attending seasonal festivals and community events that offer entertainment and fun for all ages here.
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Adult Activities

  • Hiking and Nature Walks: Explore the scenic trails in nearby parks to enjoy the natural beauty and tranquility of the area.
  • Visit Local Markets: Immerse yourself in the regional culture by browsing vibrant markets offering fresh produce and unique crafts.
  • Golfing Activities: Tee off at local golf courses that provide a relaxing yet engaging experience amid picturesque surroundings.
  • Dining Experiences: Savor a variety of regional cuisines at well-regarded restaurants, perfect for enhancing your stay here.

Other Places to Stay in Bear, DE

Delaware Rock Gym
Hullabaloo Amusement Center
Mansion House Paintball
Lums Pond State Park

Bear Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Early: Secure your ideal rentals with pools well in advance to ensure availability during peak seasons in this popular destination.
  • Explore Local Amenities: Take advantage of nearby recreational facilities and services that enhance your stay, making your visit more enjoyable and comfortable.
  • Check Property Details: Carefully review the amenities and features of your chosen rental to maximize comfort and convenience during your time here.
  • Utilize Online Resources: Use trusted booking platforms to find the best rentals with pools in the area, ensuring a seamless and reliable reservation experience.

Transportation Options

  • Delaware Transit Corporation (DTC): Offers reliable bus services throughout the region, making it convenient for you to explore local attractions without hassle.
  • Amtrak Train Service: Provides comfortable rail transportation connecting this area to major cities along the East Coast, ideal for day trips or extended stays.
  • Local Taxi and Rideshare Options: Available for quick and flexible travel within the destination, ensuring easy access to your accommodations with pools.
  • Car Rentals: Numerous rental agencies offer vehicles suited for exploring the region at your own pace, perfect for discovering nearby attractions from your rental with a pool.

Local Customs Options

  • Community Gatherings Locals in the area often host community events that emphasize togetherness and local traditions, offering you an authentic experience during your stay.
  • Food Traditions Enjoy sampling regional cuisine at local diners and eateries that showcase Delaware’s traditional dishes and hospitality.
  • Celebration of Seasons The region celebrates seasonal festivals that highlight holiday customs and seasonal changes, providing a glimpse into local culture.
  • Respect for Nature Visitors are encouraged to observe conservation etiquette and respect outdoor spaces, reflecting the community’s appreciation for its natural environment.

Frequently Asked Questions About Bear Rentals with Pools

1. What are the top Rentals With Pools 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 Rentals With Pools in Bear:

2. How many Rentals With Pools are available in Bear?

Currently, the total number of properties listed by RBO in 2026 is over 27 in the Bear area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Bear. 

3. What is the cancellation policy for rentals with pools in this area?

Cancellation policies vary depending on the specific property, so it’s best to review the listing details or contact the owner directly for information regarding refunds and any potential fees.

4. Are there specific check-in and check-out times I should be aware of during my stay?

Check-in and check-out times are determined by individual owners. Please refer to the listing or contact the host to confirm the schedule for your reservation.

5. Do rentals with pools in the region offer amenities suitable for families?

Many properties cater to families and may include kid-friendly amenities, but it’s recommended to check the listing details or ask the owner to ensure the accommodation meets your needs.

6. What are the safety features available at pools in these rentals?

Safety features such as pool fences, alarms, or covers are subject to each property’s offerings. Review the listing specifics or contact the owner for details on safety measures.

7. How do I confirm availability and secure a booking for a rental with a pool?

Availability can be checked through the listing calendar. To secure your reservation, follow the booking process outlined on the site or communicate directly with the property owner for any special requests.

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