
Holiday rentals in Bear
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Top-rated holiday rentals in Bear
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Fully Equipped Private Guest Suite Studio
Relax in a stylish guest suite studio in a quiet, safe neighborhood. Its private entrance and parking for 2 vehicles makes the cozy space all the better. Enjoy the full kitchen, work space, high speed internet (1200mbps), 50” TV, full bathroom, and more. Perfect for the business professional on-the-go, or getaway. Take a stroll through White Clay Creek Park with your furry friend. Just a short 5 minute drive from Main St.'s restaurants, local bars, and UD. Only 10 minutes from Christiana Mall.

Persimmon Pastures
A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

Appleton Retreat
This 3 bedroom, 2 bathroom home is the perfect place to get away from it all while remaining convenient to all the best that Maryland, Delaware, and Pennsylvania have to offer. Minutes from Fair Hill Natural Resource Management Area for the horseback riders, mountain bikers, hikers and nature enthusiasts. University of Delaware is a quick 10 minute ride away to catch a football game or celebrate commencement. Other local attractions - boating, fishing, vineyards and breweries.

Private Suburban Luxury Apt/Free P/min. to 95/Rt1
*Peaceful location*Quiet Suburban Area*Clean & Comfortable * Personal entrance with privacy**5 minutes from Christiana Mall*Free parking next to the entrance with large driveway* Park views. Near I-95 and Rt-1 and all major highways**Convenient & affordable for 1 night or more. *Queen bed/full kitchen/Large TV/Quality appliances Llocated in cul-de-sac/Free Wi-Fi and YouTube TV-Lower level unit. NO Smoking and NO vaping. Smoking is allowed in the driveway. A/C off for the winter

The Getaway! Romantic and Fun! Hot Tub/Dance Pole
Welcome to The Getaway. Come for a fun girls night in or for a romantic getaway and enjoy some alone time with a spacious Jacuzzi, dance pole, cuddle up by the electric fireplace, watching all your favorite movies on a 4k curved tv and mini bar with complimentary wine. You have access to a fridge , microwave and airfryer! We decorate and offer massage table! We have everything you need for an intimate experience. Book Our private & unique Basement Suite IG _thegetawayairbnb

Countryside-Stablehouse-Cozy for 2-March Discounts
Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Bohemian Minimalist Haven
Thoughtfully designed Newark stay featuring bohemian-minimalist décor, warm natural light, and pet-friendly comfort. The home includes a fully stocked kitchen and a private washer and dryer for longer or more convenient stays. Enjoy fast access to the Christiana Mall/ Fashion Blvd., University of Delaware, and dining. Located in a modest and quiet neighborhood that’s practical, central, and easy to navigate, with two dedicated parking spots directly in front of the home.

King Bed - Center of Historic District
This cute 1 bedroom apartment is located at the HEART of our lovely town. Steps away from some of the most historic places in the entire United States. Come near the weekend and you can tour our informative museums and wayside exhibits while taking in the local culture. We are a close-knit town and are happy to show out-of-towners "the way". On days we are open enjoy a $15/day credit to our cafe next door. Please enjoy your stay! We are so sorry but no pets allowed.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Upscale Glamour Retreat • Beautiful & Cozy
Welcome to your Upscale Glamour Retreat, a beautifully designed home where elegance, comfort, and modern charm come together to create the perfect getaway. Whether you’re traveling for couple relaxation, work, or a family escape, this stunning retreat offers a peaceful, upscale experience with every detail thoughtfully curated for your comfort. Convenient access to both Wilmington, Bear & Newark Delaware. Few minutes to Elkton Maryland, Philadelphia PA

Luxurious apartment/studio with private entrance
Private luxurious apartment/Studio with Bose surrounding music system, at the back of a new construction (guest suite). Everything is private, nothing is shared, private washer/ dryer (2 in one), private entrance, private bathroom kitchen and private patio. Safe place (working smoke and carbon monoxide detectors) with all amenities brand new. Close to University of Delaware ,Christiana Hospital and Christiana Mall.

Bohemia Bungalow
Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.
Popular amenities for Bear holiday rentals
Other great holiday rentals in Bear

Downtown Luxe Retreat + Free Garage Parking

Quaint studio efficiency apt.

Central 4-bedroom single fam/with private parking

Cozy Cottage near it all in Wilmington

In the Circle, UD, Sports, D Park, tax free Shoppn

Modern Guesthouse Retreat

BlueHenNest: walk to UD, 3 BR/1BA/free parking/EV

Luxury House
Frequently Asked Questions
What are the best places to stay in Bear?
Vacation rentals in residential neighborhoods of Bear are frequently suggested for their quiet surroundings and access to green spaces. Staying near the center or in family-friendly areas can make it easy to reach parks, shops, and dining.
What are the best things to do in Bear with kids?
Kids often enjoy playgrounds in local parks, visits to pick-your-own farms during harvest season, and community recreation centers with family activities. Nature trails also provide opportunities for easy walks and outdoor discovery.
What are some of the best things to do in Bear?
Explore nature trails and community parks, visit local farms for seasonal produce, or discover nearby historical sites. Many visitors also enjoy outdoor recreation and casual dining with locally inspired dishes.
How is the weather in Bear?
Bear experiences cold winters around 26–41°F (-4–5°C) with some rainfall, and warm, humid summers near 68–87°F (20–31°C). Spring and fall bring milder temperatures and colorful foliage, making them pleasant times for outdoor activities.
When is the best time to visit Bear?
Late spring and early fall are often recommended, with milder temperatures and comfortable weather for outdoor activities. Summer brings warmer afternoons, while winter is quieter and features holiday events.
What are the best places to visit in Bear?
Parks with nature trails, small lakes, and picnic areas are frequently suggested, along with family farms when fruit is in season. The Bear area also has community centers and locally owned eateries to explore.
What are some hiking trails in Bear?
Bear has several local parks and nature preserves with walking and hiking trails, suitable for most experience levels. wooded paths, wetland boardwalks, and open fields create a variety of scenic walks.
What are some family activities we can do in Bear?
Bear has parks with playgrounds, open fields for games, and nature centers that sometimes host family-friendly programs. Local farms often invite guests for seasonal fruit picking and hands-on activities.
What are some of the best day trip ideas from Bear?
Day trips from Bear can include exploring nearby historic towns, museums, botanical gardens, and state parks with scenic trails. Coastal areas and cultural sites around the region are also popular with visitors.
Are there any pet friendly accommodations available in Bear?
Bear has a selection of pet friendly vacation rentals, especially in residential neighborhoods known for green spaces and walking trails. Some hosts welcome pets and may provide recommendations for nearby parks, so check individual listings for details.
What are some local tips for visiting Bear?
Locals suggest bringing comfortable walking shoes to explore parks and nature trails, and sampling fresh produce at markets and farms. Layered clothing is helpful due to changing seasonal temperatures and occasional rain.
What is Bear known for?
Bear is known for its blend of suburban comfort and access to natural spaces, such as parks and nearby farmlands. The area has ties to agricultural traditions and is recognized for community-driven activities.
What are the best hidden gems to explore in Bear?
Bear has peaceful local parks, nature preserves with walking paths, and tucked-away family farms where you can pick fruit in season. Birdwatching spots and small community gardens invite quiet moments of connection with the outdoors.
What are the best foods to try in Bear?
Bear’s dining scene has American classics, farm-fresh produce, and locally inspired baked goods. Crab dishes, soft pretzels, and seasonal fruit desserts are often recommended, reflecting Delaware’s food traditions.
What should I bring for a trip to Bear?
Pack clothing suited to the season—layers work well—and bring a waterproof jacket or umbrella, as rain is common throughout the year. Comfortable walking shoes are helpful for exploring parks, trails, and community spaces.
What is the nightlife in Bear like?
Bear has a relaxed nightlife scene, with local bars, casual restaurants, and occasional live music in the area. Many visitors opt for informal gatherings or evening strolls in nearby parks.
What are the most popular events or festivals in Bear?
Seasonal fairs, farmers’ markets, and community festivals are frequently suggested, especially during late spring and fall. Nearby, larger towns may host concerts, cultural celebrations, and holiday events that draw visitors from Bear.
Are there family friendly vacation rentals in Bear?
Many vacation rentals in Bear have family-friendly features such as extra bedrooms, kitchen facilities, and access to outdoor spaces. Residential neighborhoods are often suggested for their quiet atmosphere and proximity to parks.
Quick stats about holiday rentals in Bear

Total holiday rentals
Explore 30 holiday rentals in Bear

Nightly prices starting at
Bear holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 920 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Bear holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Bear rentals

4.8 Average rating
Bear stays are highly rated by guests – averaging 4.8 out of 5!
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