
House vacation rentals in Bear, Delaware
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Top-rated house rentals in Bear, Delaware
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

Cottage w/ King Bed & Private Backyard ~ Dogs OK
Welcome to The Cottages on Orchard, a 1BR/1BA cottage built in 1920 by author Victor Thaddeus. Nestled on a natural wooded lot this rustic cottage is one of three cottages, perfect for up to 2 guests & their furry companions. Conveniently located in whimsical Ardentown, Delaware, you’ll be only 2 minutes from I-95 South & 10 minutes from downtown Wilmington, offering easy access to local attractions. Enjoy the private backyard, woods, hiking trails, creek, & more. (READ HOUSE RULES)

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!

The Historic Walton House by RPG
✨ The Walton House, built in 1846, is located in the National Historic District of Kennett Square, PA. We are walking distance to downtown Kennett Square and a short drive to local Brandywine Valley points of interest. ✨ The home has been lovingly maintained to reflect its mid 19th century beginnings, while providing a modern, comfortable place to rest while visiting our lovely town. We hope you enjoy the home as much as we do!

3 Bed/1.5 Bath + 2MI - University of Delaware
✨ Cozy Home Near the University of Delaware Welcome to your home away from home in Newark, DE! This cozy retreat is ideally located within walking distance from the University of Delaware, making it perfect for visiting students, families, and alumni. Nestled in a vibrant neighborhood, you'll find yourself surrounded by an abundance of shopping options, great golf courses, top-notch restaurants, and inviting coffee shops.

Waterfront Retreat for Weekends and More!
Nature at its finest: Find peace and tranquility in this waterfront home with breathtaking water views from all freshly decorated rooms. Enjoy the water traffic on the C&D Canal along with the multitude of wildlife living in the area. Launch your kayak, canoe or row boat from the boat ramp. Relax here in the evenings while spending the day visiting the University of Delaware or other local Cecil County venues.
Popular amenities for Bear, Delaware house rentals
House rentals with a pool

Contractors Love Us! Your workers will love you

Cozy 4BR Parkesburg Home with Pool & Sunroom

Waterfront Winter on the river 2025/26 available!

The Mint Cottage in Chesapeake City

Modern Farmhouse: Pool, Hot Tub & Pickleball

Cording Lodge*Pool*Pickleball/Basketball court

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

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

Relaxing Ranch Getaway near Christiana Mall & Univ

Central 4-bedroom single fam/with private parking

Water View Historic B & B - Gift Card Included

Exquisite Loft Downtown w/parking, fireplace

Miss Francis Kirk House/Luxury 2Bed/1.5Bath

Stay-4-Awhile

Newly built Tiny House in Historic Kennett Square

A home away from home.
Private house rentals

Charming 4BR in Historic District

Delightful 2BR River View Home!

Huge Sun Soaked Apt In Quiet Neighborhood

Sunset River Cottage

Sweet Bay Overlook

Cozy Townhome w/ Private Parking

Petals & Porch – Peaceful DE Stay

Central Christiana Modern
Quick stats about house rentals in Bear, Delaware

Total vacation rentals
Explore 20 vacation rentals in Bear, Delaware

Nightly prices starting at
Bear, Delaware vacation rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 250 verified reviews to help you choose

Wi-Fi availability
20 of Bear, Delaware vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
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- Pennsylvania Convention Center
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- Longwood Gardens
- Fairmount Park
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- Philadelphia Museum of Art
- 30th Street Station
- Diggerland
- French Creek State Park
- Wells Fargo Center
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- Philadelphia Zoo
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- The Franklin Institute
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- Valley Forge National Historical Park
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- Independence Hall
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- Eastern State Penitentiary