Vacation rentals in Bear

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Top-rated vacation rentals in Bear

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Guest favorite
A spacious living area is shown, featuring a well-equipped kitchen, dining space for four, and a cozy seating area. Light green chairs provide a pop of color, while a large mirror reflects the room's dimensions. Soft natural light filters in from the window.
Guest suite in Newark
4.95 out of 5 average rating, 189 reviews

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.

Top guest favorite
A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.
Cottage in North East
4.98 out of 5 average rating, 667 reviews

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.

Top guest favorite
A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.
Home in Perryville
4.97 out of 5 average rating, 151 reviews

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Top guest favorite
A single-story home is set on a green lawn, featuring a prominent American flag and a Maryland state flag. The covered porch is accessed by a set of blue double doors, and a dark-colored vehicle is parked in the carport.
Home in Elkton
4.96 out of 5 average rating, 161 reviews

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.

Superhost
The interior space is designed with an open layout, featuring a living area with a comfortable gray sofa and a small coffee table. A full kitchen with modern appliances is visible, alongside cabinets and a dining setup. Soft lighting brightens the wood-style flooring.
Apartment in New Castle
4.94 out of 5 average rating, 161 reviews

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

Guest favorite
Guest suite in Bear
4.95 out of 5 average rating, 134 reviews

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

Guest favorite
An open layout showcases a dining area with a light-colored table set for six, adjacent to a cozy living space featuring a neutral-toned sofa and armchairs. A horse-themed artwork is displayed on the wall, while soft curtains frame the windows allowing natural light in.
Guesthouse in Elkton
4.91 out of 5 average rating, 187 reviews

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

Guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 260 reviews

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...

Top guest favorite
Home in Newark
5 out of 5 average rating, 6 reviews

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

Guest favorite
The kitchen area is equipped with stainless steel appliances and granite countertops. A microwave and coffee machine are visible, alongside cabinets showcasing various kitchen supplies. A colorful mat lies on the polished wooden floor, and a wall clock is mounted above the countertop.
Guest suite in Bear
4.88 out of 5 average rating, 244 reviews

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.

Top guest favorite
A welcoming porch features white adirondack chairs and a small blue table. A lantern and a decorative container are placed nearby, with the house's yellow exterior and orange shutters providing a cheerful backdrop. The view includes trees and street activity.
Cottage in Chesapeake City
5 out of 5 average rating, 112 reviews

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.

Guest favorite
The exterior of the two-unit apartment building is presented, showcasing a covered porch with seating and steps leading to the second floor. Surrounding grassy areas and trees contribute to a serene atmosphere, with fields visible in the distance.
Apartment in New Castle
4.88 out of 5 average rating, 452 reviews

Blue Tranquility-Pvt Apt for Quiet Rest

Blue Tranquility is the first floor apartment (apartment A) in a two unit apartment building. It is a cozy one bedroom unit with a large covered porch located on the grounds of the famous Egyptian house. The unit is comfortable for 2 people but will accommodate 4 with the living room couch converting to a bed. The property is conveniently located with plenty of off street parking.

Popular amenities for Bear vacation rentals

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 vacation rentals in Bear

  • Total vacation rentals

    Explore 30 vacation rentals in Bear

  • Nightly prices starting at

    Bear vacation rentals start at G$6,275 GYD 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

  • Wi-Fi availability

    30 of Bear vacation rentals include wi-fi 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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