
House holiday rentals in Bear, Delaware
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Top-rated house rentals in Bear, Delaware
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Cute, cozy and convenient 2BR w/ office
Come relax and enjoy our renovated and stylish home. You’ll be minutes from 95, the Riverfront, Union Street, Trolley Square and downtown restaurants and bars. A perfect place for a work trip, a girls/guys weekend, a visit to see friends or family, and for hosting a dinner party (which we love to do!). Our home is a block away from Canby Park, and is in the family-friendly neighborhood of Bayard Square. The house has all the conveniences you could need, and if you need something, just ask!

Christiana Cottage, Cozy home located near Gap.
The cottage is located in the town of Christana on a quiet street with a spacious deck and backyard. The home is owned by the Lapp family and managed by my husband Paul and I. The cottage has 2 BDRMS w queen beds and a daybed to sleep 1 guest. The newly renovated bath offers a shower/tub combo. Dutchway Grocery store & Restaurant is just around the corner. Amish attractions, Sight and Sound, Strasburg, Outlet shopping within 20 min drive of the home. Smart TV to log into your accounts. WIFI .

Eclectic Escape Near Longwood Gardens & Mt. Cuba
Home information: Home owners are on the other side of house ( your space is very private). 1/2 the house is your space. Imagine a ranch house cut down the middle and 1/2 is the Airbnb and the other 1/2 is the owners side. Private entrance with keyless lock , 2 bedrooms with Queen beds, private bathroom and a living room. Other features include: Wifi , TV’s , a small refrigerator/freezer , microwave, coffee maker and a Private 1 acre lot w/ parking ( 2 cars max). There is no kitchen .

Historic J. Pyle House Main St Location Pets 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

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!

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.

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.

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.

Welcome to The Richfield!
Just minutes from U of D and the Bob Carpenter Center, tax free shopping at the Christiana Mall, and scenic walks at Rittenhouse park. A perfect oasis for the whole family to enjoy with a touch of sophistication for any business trip. Enjoy 2 floors of entertainment space with 2 50' TVs, Foosball Table, and a Dartboard to pass the time. A coffee bar will help kick start your day, while the complementary bottle of wine will help you relax at the end.

Beachfront Sunsets on the Water at Oakwood Beach
You’ll instantly relax when you arrive at this private beachfront home on the beautiful Delaware River (2020 River of the year!). This hidden gem is off the beaten path, making it perfect for you to escape the hustle and bustle of your busy day-to-day. You’ll love the amazing sunsets and water fun — walk out the back door directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

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 king 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.

The Mineral House of West Chester
Unique home in the heart of West Chester, tastefully renovated with fantastic detail, walking distance to all the dining, bars, shops and parks the borough has to offer. This home will bring you back to WC again and again. Do not let the staircase frighten you, it was designed by the late great architect George A Matuszewski for this unique space. Come and enjoy this special property and all the charm West Chester has to offer.
Popular amenities for Bear, Delaware house rentals
House rentals with a pool

Contractors Love Us! Your workers will love you

Breathtaking Waterfront w/pool and private dock

Historic Victorian Queen Chesapeake City

The Mint Cottage in Chesapeake City

Cording Lodge*Pool*Pickleball/Basketball court

Comfort, Fun, & charming! - 5BR oasis w/ Pool

Heated Pool • Private Backyard • Home Theater

Sweet home w/pool & woods at peaceful Glen Mills
Weekly house rentals

Charming 4BR in Historic District

Central 4-bedroom single fam/with private parking

Exquisite Loft Downtown w/parking, fireplace

Miss Francis Kirk House/Luxury 2Bed/1.5Bath

Sweet Bay Overlook

Cozy|PrivateHome|Driveway|Near Mall & U of D

Cozy Townhome w/ Private Parking

Make yourself at HOME!
Private house rentals

Radiant 4-Bed Haven w/ King suite in N. Wilmington

Stunning Chesapeake Bay views, 5 bedrooms, 3 bath

Sunset River Cottage

Waterfront House on the Upper Chesapeake Bay

Home away from home between Wilmington/Newark

Modern spacious townhome Newark

Amish Countryside Escape at Forest Edge Farm

Cozy 2-BR Retreat Private Parking Near Downtown
Quick stats about house rentals in Bear, Delaware

Total holiday rentals
Explore 20 holiday rentals in Bear, Delaware

Nightly prices starting at
Bear, Delaware holiday rentals start at $45 AUD per night before taxes and fees

Verified guest reviews
Over 250 verified reviews to help you choose

Wi-Fi availability
20 of Bear, Delaware holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Bear, Delaware rentals

4.6 Average rating
Bear, Delaware stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Longwood Gardens
- Fortescue Beach
- Fairmount Park
- Penn's Landing
- Philadelphia Museum of Art
- Betterton Beach
- Wells Fargo Center
- Diggerland
- French Creek State Park
- Philadelphia Zoo
- Marsh Creek State Park
- Aronimink Golf Club
- The Franklin Institute
- Big Stone Beach
- Wissahickon Valley Park
- Valley Forge National Historical Park
- Crystal Beach Manor, Earleville, MD
- Independence Hall
- Franklin Square
- Eastern State Penitentiary
- Philadelphia Cricket Club




