Vacation rentals in Bear

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Top-rated vacation rentals in Bear

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Apartment in Trinity Vicinity
5 out of 5 average rating, 11 reviews

Trenton Place Modern Luxury Designed For You

Trenton Place Modern Luxury · Historic Charm · Designed for You Experience refined comfort where modern design meets timeless character. This beautifully curated apartment features high-end finishes, sleek furnishings, and designer details throughout — from the quartz countertops and black matte fixtures to the custom lighting and elegant décor. Located in Wilmington’s historic district, Trenton Place offers the perfect balance of style and serenity. It's ideal for professionals and couples.

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
4.96 out of 5 average rating, 186 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.

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, 146 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!

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, 177 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
A spacious living area showcases a soft sofa, stylish armchair, and a wooden coffee table. A ceiling fan rotates gently above, while large windows allow natural light to illuminate the room. The dining area features a wooden table surrounded by six chairs, suited for gatherings.
Home in Newark
4.95 out of 5 average rating, 115 reviews

2 BR/1 BA/Office University of DE

Home of the fighting Blue Hens and the University of Delaware, Newark is centrally located to Philadelphia, Baltimore and surrounded by over 12,000 acres of beautiful parkland. Enjoy this recently renovated home with spacious rooms, a fully equipped kitchen and laundry and plenty of off-street parking. Every detail has been thought of for your comfort including free WIFI. Great for UD Events, Weddings, Anniversaries, Car Shows, Mountain Biking and Cycling Weekends, and more.

Guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 249 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
Condo in Newark
4.92 out of 5 average rating, 36 reviews

Quiet condo near Christiana, UD, Wilmington | Desk

✨ Spacious Newark Getaway Near Christiana & UD Welcome to your home away from home in the heart of Newark, Delaware! 🌿 Our peaceful and secluded retreat is tucked away in a quiet neighborhood yet just minutes from Christiana Hospital, Christiana Mall, the University of Delaware, and downtown Wilmington. Whether you’re visiting for work, family, or leisure, this bright and spacious home is designed for both comfort and convenience.

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, 241 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, 108 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, 447 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.

Top guest favorite
A charming cottage is nestled among lush greenery, with a large window inviting natural light. The exterior features a sloping roof and a stone wall, accentuating the surrounding landscape of rolling hills and fields.
Cottage in Coatesville
5 out of 5 average rating, 330 reviews

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.

Popular amenities for Bear vacation rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Bear?

    Bear has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Bear?

    Experience the best of Bear with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Bear?

    Yes! Work meets play with ease at over 10 vacation rentals in Bear featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Bear?

    Make yourself at home in Bear by choosing from our most frequently booked neighborhoods. We have over 80 vacation rentals in Glendale, and over 80 vacation rentals in Becks Woods.

  • Do house rentals in Bear have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Bear. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bear have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Bear. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bear have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Bear. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Bear have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Bear. Enjoy a tailored experience with all the comforts you desire.

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$6,277 GYD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • 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

  • 4.7 Average rating

    Bear stays receive an average rating of 4.7 out of 5 from guests

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