111+ Bear Holiday Rentals & Private Villas

Discover more than 111 holiday rentals in Bear. PickleTrip™ holiday homes has everything you need to find a place to stay near Bear, DE.

Whether you are looking for luxury villas in Bear, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Bear with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Bear for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Bear with PickleTrip™. Stay and play pickleball when you travel.