
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.

Historic Downtown D. Clark House Dog Friendly!
The historic Dorothy Clark House, built around 1907, is in the National Historic District of Kennett Square, PA. We are downtown in the heart of the walkable Kennett Square Borough! This twin home has been lovingly restored to reflect its early 20th century roots, while providing a cozy place to relax while visiting our quaint town. We hope you’ll fall in love with the home like we have! 45 min to Philadelphia airport, 25 min to Wilmington 25 min to WCU, 6 min to Longwood, 15 min to Winterthur

Cozy Cottage Elkton North East 3bed 2 bath Patio
Hacienda on the Hill! Perfect country & city location! Close to North East activities, fishing tournaments & shows. Newark& UofDE(20min). Sandy Cove & North Bay(20 min). Quiet, end of gravel road location. Offering 3 bedrooms 2 full baths & stocked kitchen. Backyard patio w/seating, & fire pit. The best part, just 1 mile to quaint downtown North East with free parking!! 1 mile from seafood, mexican, steak house, coffee shops, grocer, convenience store etc. Relax, visit, enjoy each other NO TV's

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 .

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.

Longwood | Shops & Restaurants | Private Backyard
"We've stayed at AirBnBs all over the world and this was our favorite!" • Walk Score 86 (Walk to cafes, dining, shopping, breweries, etc.) • Fully equipped + stocked kitchen w/ SMEG appliances • Backyard patio w/ fire pit + BBQ grill • Samsung Frame TV • Onsite washer + dryer • Extremely safe neighborhood • Self check-in w/ keypad → 2 mins to Downtown → 10 mins to Longwood Gardens (#1 Botanical Gardens in USA) → 15 mins to Brandywine Battlefield → 25 mins to downtown Philly

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.

Cozy cottage on beautiful dairy farm in Strasburg
Tranquil. Refreshing. Restful. These are the perfect words to describe Graystone Cottage, located on a working dairy farm just outside the quaint historic town of Strasburg in Lancaster County, PA. Built in 1753, this 1000 square feet, newly restored limestone cottage was the original settlement home on the 135-acre homestead. Boasting a French country esthetic, this little darling has the most captivating views of rolling hills, a brook, and lush green farmland.

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.

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.
Popular amenities for Bear, Delaware house rentals
House rentals with a pool

Findley Farm View Cottage (Outdoor Pool!)

Creek front home *heated pool open year round!*

Waterfront Winter on the river 2025/26 available!

Modern Farmhouse: Pool, Hot Tub & Pickleball

Wood Country Bungelow - Fall Getaway!

Cording Lodge*Pool*Pickleball/Basketball court

Sweet home w/pool & woods at peaceful Glen Mills

Spacious 4-bedroom house with a private pool.
Weekly house rentals

Charming 4BR in Historic District

Home away from Home

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

A home away from home.

Cute, cozy and convenient 2BR w/ office

Petals & Porch – Peaceful DE Stay

Bohemian Minimalist Haven

The Cozy Corner in N. Wilmington w/ Queen Bed
Private house rentals

Relaxing Ranch Getaway near Christiana Mall & Univ

Water View Historic B & B - Gift Card Included

Miss Francis Kirk House/Luxury 2Bed/1.5Bath

Sunset River Cottage

Sweet Bay Overlook

Make yourself at HOME!

Cozy 2-BR Retreat Private Parking Near Downtown

A Cool Place to Stay, Wilm DE
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 $42 CAD per night before taxes and fees

Verified guest reviews
Over 250 verified reviews to help you choose

Wifi availability
20 of Bear, Delaware vacation rentals include wifi 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
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
- 30th Street Station
- Diggerland
- Wells Fargo Center
- French Creek State Park
- Marsh Creek State Park
- Philadelphia Zoo
- The Franklin Institute
- Big Stone Beach
- Aronimink Golf Club
- Valley Forge National Historical Park
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD
- Independence Hall
- Franklin Square
- Eastern State Penitentiary




