
Holiday rentals in Bear
Find and book unique accommodation on Airbnb
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.

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...

Silo Suite
Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Boardwalk- Modern Oasis with King Bed, Fast WiFi
Escape to our stylish ground-floor apartment in Wilmington's historic Cool Springs district. This 1-bedroom retreat fits 2 guests and features a king bed, workspace, and modern kitchen. Perfect for couples or business travelers seeking a blend of historic charm and modern comfort. Located in an 1800s building, you're minutes from the Riverfront and downtown. (We require ID, signed agreement, and a $500 security deposit may be charged at the host's discretion)

A-Frame Tiny Home Retreat - With Sauna & Hot Tub!
Perfect for a romantic getaway, or a peaceful time in nature. The A-frame is one of the best scenic experiences you will find! With heat and AC, a luxurious bed, kitchenette, outdoor rain shower, bath house, sauna, hot tub, flat top griddle and the unparalleled connection to nature – Robes also provided! What better way to spend a few nights to fully re-energize yourselves! If your lucky, you may even see some deer or turkey feeding in the cornfield :)

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 holiday rentals
Other great holiday rentals in Bear

Modern 1BR Condo Free Parking- Heart of Wilmington

Casa Domino: A Peaceful Waterfront Retreat

Cozy 1 BR/1 BA near UD/Christiana Hospital

Cozy Cottage near it all in Wilmington

Modern Guesthouse Retreat

Modern Tiny Home w/Salt Water Hot Tub

Tilton Park Loft Studio

Chic home by University of Delaware, Christiana
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 holiday rentals in Bear

Total holiday rentals
Explore 30 holiday rentals in Bear

Nightly prices starting at
Bear holiday rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

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

4.7 Average rating
Bear stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Outer Banks Holiday rentals
- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Longwood Gardens
- Fairmount Park
- Philadelphia Museum of Art
- Wells Fargo Center
- Penn's Landing
- Diggerland
- Dutch Wonderland
- Betterton Beach
- University of Pennsylvania
- 30th Street Station
- Philadelphia Zoo
- French Creek State Park
- The Franklin Institute
- Marsh Creek State Park
- Wissahickon Valley Park
- Valley Forge National Historical Park
- Independence Hall
- Eastern State Penitentiary
- Franklin Square
- Spruce Street Harbor Park
- Ridley Creek State Park




