
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.

Hygge Haven: A cozy apartment in a canal-side town
Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

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.

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!

Refined Lavender Farm Escape with a Luxurious Spa
Escape to Windy Hill Lavender Farm, a luxurious countryside retreat surrounded by rolling hills and fragrant lavender blooms. Unwind in a spa-style bathroom with a tiled walk-in shower and deep soaking tub, then relax in the cozy queen bedroom or loft with 2 twin beds . Savor starry nights in the hot tub on the spacious deck, grill in the charming corncrib area, and gather by the fire pit. Perfect for romantic getaways, peaceful escapes, and unforgettable memories in nature’s beauty.

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

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.

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...

Cottage Just Off North East's Main Street
Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

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.

Cozy, Creative, One of a Kind
Enjoy activities (ping-pong/dart/board games), then stretch out in the king size bed. Full of host's original art. Driveway parking 10 minutes or less to all that Kennett has to offer (breweries, restaurants, Longwood Gardens, etc.), 1/2 hour to Wilmington or UD, 1 hour to Philadelphia. We live upstairs and you will hear footsteps in the morning before school and afternoons. *Solar Powered*Woman Owned*EV Charger*
Popular amenities for Bear vacation rentals
Other great vacation rentals in Bear

Casa Domino: A Peaceful Waterfront Retreat

Carriage House in Landenberg

Your own peaceful, natural retreat!

“McDaniels Corner” (Cozy Home in North Wilmington)

Charming loft apartment

The Loft On Forever Lane

Spacious 4-bedroom house with a private pool.

Cozy Loft Above Ink Shop
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 € 26 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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- Pennsylvania Convention Center
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- Eastern State Penitentiary
- Franklin Square
- Ridley Creek State Park
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