
House holiday rentals in Bear
Find and book unique houses on Airbnb
Top-rated house rentals in Bear
Guests agree: These houses are highly rated for location, cleanliness and more.

Historic J. Pyle House Main St Location Dogs OK!
The J. Pyle House, built in 1844, is in the National Historic District of Kennett Square, PA. We are in the heart of walkable downtown Kennett Square and a quick 6 minute drive to Longwood Gardens. The townhome has been lovingly restored to reflect its mid-19th century roots, while providing an updated, cozy place to relax while visiting our quaint town. 45 min to the PHL airport, 25 min to Wilmington, DE, 25 min to West Chester University, 6 min to Longwood Gardens 15 min to Winterthur
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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!
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“Home Away from Home” in Rising Sun, Maryland
PLEASE READ *BEDROOM 3 is a suite that can be added for an extra charge (see pics) * It includes a living area, king size bed, bathroom and kitchenette. Ask Karen for pricing to add. Without the suite there is a foyer leading to a large living room, kitchen with dining area, 2 bedrooms with queen beds and a full bath. This home is comfy and has a history room showing family collectibles dating back to 1854.... Children under 12 years of age are not suitable and No Pets are allowed.
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Red Point Lighthouse
Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.
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Historic Creekside Home - 2br 2.5ba Downtown
Built in 1875, this newly renovated two bedroom home, is centrally located in downtown North East. Modern finishes and an open concept living space compliment the original wood floors, clawfoot tub and exposed brick walls. All the amenities of Main Street are steps away, yet the home is tucked away on a quiet street with a creek in the back yard. Our home is 2.5 miles from I-95 and one block from North East Community Park, Anchor Marina and the headwaters of the Chesapeake Bay.
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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.
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Spacious 4-bedroom house with a private pool.
This spacious and cozy family house is in a peaceful quiet neighborhood for work-related comfort and maximum relaxation. The house is offering you a fully equipped kitchen, free wifi, air conditioning, washer and dryer, cozy furnitures, free parking, a beautiful fenced backyard with a huge deck and a relaxing outdoor sitting, a barbeque grill, a private swimming pool, and a kids playground. Everything you need for a relaxing stay is right in this home.
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Newly built Tiny House in Historic Kennett Square
Custom-built tiny house Cottage with designer touches. Main floor has living area, full bath, and laundry. Loft bedroom with queen bed and full ceiling height, accessed by stairs. Fully equipped kitchen with full appliances, cookware, table settings, and coffee. Smart TV, high-speed internet, and on-site parking. Two blocks from downtown Kennett Square dining, shops, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Max 2 guests.
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Cozy Townhome w/ Private Parking
Enjoy this comfy townhome centrally located near I-95 and I-495. It is also 10 minutes to the Wilmington Riverfront and downtown attractions; less than 30 minutes to Philadelphia International Airport and Philadelphia Center City. This home has two spacious bedrooms- one which contains a queen bed and the other with two XL twin beds (that can be converted into a king bed upon request). The basement and one bedroom closet will not be accessible.
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The Lighthouse
Centrally located in northern Delaware with easy on/off access to 95 and 495. Newer construction, built in 2018. One large bedroom with KING size bed, 1.5 bath, private entrance, living room and full eat in kitchen. Work station area. Twin size pull out in living room. Free WiFi and large smart TVs in living room and bedroom. Deck off of the kitchen and upstairs deck off of the bedroom. Laundry located in bedroom upstairs. NO CLEANING FEE
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*Woodland Chalet* Hot Tub - Fire Pit - Grill
Welcome to your cozy woodland retreat! Nestled in a serene forest, this charming one-bedroom Airbnb offers a perfect blend of style and tranquility. Designed with a modern aesthetic, the space features chic furnishings, warm modern accents, and large windows that invite natural light and breathtaking views of the surrounding trees.
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Modern 3 bedroom ranch house/5 min from UD
Discover the perfect blend of comfort and convenience at this modern ranch style home in the heart of Newark. Just minutes from the University of Delaware and the scenic Newark Reservoir, this fully updated space is ideal for families, friends, or visiting professionals looking to relax in comfort while staying close to it all.
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Popular amenities for Bear house rentals
House rentals with a pool

Private Pool and Hot tub with Views!
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Quiet Country Home in Parkesburg, In Ground Pool
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Breathtaking Waterfront w/pool and private dock
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Modern Farmhouse: Pool, Hot Tub & Pickleball
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The Mint Cottage in Chesapeake City
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Cording Lodge*Pool*Pickleball/Basketball court
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Comfort, Fun, & charming! - 5BR oasis w/ Pool
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Sweet home w/pool & woods at peaceful Glen Mills
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Weekly house rentals

Perfect for work assignments or family stays
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Waterfront Retreat for Weekends and More!
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Water View Historic Tennis Club - 3br 2.5bath
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Sunset River Cottage
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Beautiful Large Home in Private Woods with Hot Tub
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Make yourself at HOME!
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Bohemian Minimalist Haven
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Upscale Glamour Retreat • Beautiful & Cozy
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Private house rentals

Private Guest Suite
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The River House - waterfront
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Casa Domino: A Peaceful Waterfront Retreat
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Radiant 4-Bed Haven w/ King suite in N. Wilmington
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Sleek Modern Villa - Centrally Located
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Central 4-bedroom single fam/with private parking
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Stunning 2BR Cottage w/River views
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Stunning Farmhouse near Christiana Mall Newark, DE
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Quick stats about house rentals in Bear

Total holiday rentals
Explore 10 holiday rentals in Bear

Nightly prices starting at
Bear holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

Wi-Fi availability
10 of Bear holiday 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
Destinations to explore
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- Lincoln Financial Field
- Pennsylvania Convention Center
- Longwood Gardens
- Citizens Bank Park
- Wells Fargo Center
- Fairmount Park
- University of Pennsylvania
- Philadelphia Museum of Art
- Dutch Wonderland
- Betterton Beach
- Diggerland
- Philadelphia Zoo
- Dover Motor Speedway
- Temple University
- 30th Street Station
- French Creek State Park
- University of Delaware
- Marsh Creek State Park
- Drexel University
- Valley Forge National Historical Park
- Independence Hall
- Greater Philadelphia Expo Center & Fairgrounds
- Wissahickon Valley Park
- Eastern State Penitentiary





