Photo by KM Moore

Bear Holiday Rentals

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Holiday Rentals in Bear

Cozy loft above ink shop

Bear
9.4 out of 10, Exceptional, (3)
"Host was extremely responsive, place was in a great location for the lacrosse tournament we played in. Plenty of room, everything was great."
United States
Jeffrey R.
The price is AU$166
includes taxes & fees
17 Nov - 18 Nov
Cozy loft above ink shop

Nature's Haven Tiny Home

Bear
10.0 out of 10, Exceptional, (4)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is AU$363
includes taxes & fees
20 Nov - 21 Nov
Nature's Haven Tiny Home

Tiny Home Tranquil Oasis

Bear
The price is AU$374
includes taxes & fees
18 Nov - 19 Nov
Tiny Home Tranquil Oasis

Heated Pool • Private Backyard • Home Theater

2.0 star property
Middletown
The price is AU$814
includes taxes & fees
25 Nov - 26 Nov
Heated Pool • Private Backyard • Home Theater

Country Get Away 1 Bedroom Apartment

Elkton
9.8 out of 10, Exceptional, (40)
"The hosts were amazing and enjoyed talking with them. We look forward to coming back soon. Sean and Paula "
United States
Michael B.
The price is AU$173
includes taxes & fees
24 Nov - 25 Nov
Country Get Away 1 Bedroom Apartment

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

2.0 star property
Wilmington
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is AU$560
includes taxes & fees
20 Nov - 21 Nov
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

Stylish Private Suite in the heart of Brandywine Valley

Wilmington
10.0 out of 10, Exceptional, (190)
" Very nicely decorated, plenty of space and great location can't wait to come back."
United States
Mark S.
The price is AU$309
includes taxes & fees
17 Nov - 18 Nov
Stylish Private Suite in the heart of Brandywine Valley

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Wilmington
8.6 out of 10, Excellent, (12)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
United States
Douglas R.
The price is AU$270
includes taxes & fees
17 Nov - 18 Nov
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

2.0 star property
Elkton
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$249
includes taxes & fees
22 Nov - 23 Nov
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Underground Railroad Barn

Kennett Square
9.8 out of 10, Exceptional, (26)
"Great property. Good for dogs, full fenced in yard. "
United States
David R.
The price is AU$443
includes taxes & fees
17 Nov - 18 Nov
Underground Railroad Barn

Welcome to the Mushroom Capital of the World!

Kennett Square
10.0 out of 10, Exceptional, (11)
"I love how artistic and unique this lodging is! Owner is a mixed media artist and her unique artwork and eye are represented throughout the space. It was clean and very comfortable. Many extra amenities were in the space. I always enjoy a king size bed and it was very comfortable. Our extra guest slept well on the couch made into a bed easily. We had one issue, I've never encountered before with this type of lodging - we did not receive any check in information and the host was not...
United States
Julie H.
The price is AU$233
includes taxes & fees
17 Nov - 18 Nov
Welcome to the Mushroom Capital of the World!

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
The price is AU$431
includes taxes & fees
17 Nov - 18 Nov
Historic Chesapeake City Stay

Room #2 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
The price is AU$180
includes taxes & fees
17 Nov - 18 Nov
Room #2 in Elkton, MD – Easy Access to I-95

Thunder Hill Retreat - Spacious/Deck/Hot tub

Lincoln University
10.0 out of 10, Exceptional, (16)
"Great property, space and location for the boys and dad to have there own space, big elk creek for fishing and grill was fabulous to do chicken and burgers for a large group"
United States
Richard F.
The price is AU$737
includes taxes & fees
19 Nov - 20 Nov
Thunder Hill Retreat - Spacious/Deck/Hot tub

New Construction townhome close to everything downtown w/transparent pricing

Wilmington
9.8 out of 10, Exceptional, (19)
"Beautiful home. Lisa was so lovely to specially set up a room for my 86 year old mother! We would not hesitate to stay again!!"
United States
becky m.
The price is AU$317
includes taxes & fees
23 Nov - 24 Nov
New Construction townhome close to everything downtown w/transparent pricing

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

2.0 star property
Newark
10.0 out of 10, Exceptional, (3)
"Det var super ophold og god service "
Denmark
Claus R.
The price is AU$451
includes taxes & fees
20 Nov - 21 Nov
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Luxury Condo + Free Garage Parking 402

Downtown Wilmington
The price is AU$320
includes taxes & fees
1 Dec - 2 Dec
Luxury Condo + Free Garage Parking 402

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The dome and surrounding areas looks like it does in the photos, and using the compost toilet, shower, etc were pretty easy even for a camping novice like myself. The farm is beautiful and quiet. Good opportunities for birding too. I never saw or heard the gentlemen who live in the farmhouse, I only saw their cars come and go. I came here for rest and a connection to nature, and that’s what I got. I’d love to come back in the future! I think it would be even nicer later in the spring."
United States
Lady N.
The price is AU$257
includes taxes & fees
20 Nov - 21 Nov
Summer Rustic Camping with AC and King Bed

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Newark
9.8 out of 10, Exceptional, (19)
"This place is beautiful in a quiet neighborhood. The kitchen is well stocked, the bed are so comfortable and the bathrooms are very nice, especially the master bath!!! I'd definitely stay here again."
United States
Lisa Y.
The price is AU$516
includes taxes & fees
23 Nov - 24 Nov
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens

Kennett Square
10.0 out of 10, Exceptional, (35)
"Everything was thought of and our host was so responsive and helpful. Loved our stay, we’ll be back! "
United States
Anya M.
The price is AU$513
includes taxes & fees
17 Nov - 18 Nov
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bear Hotel Reviews

Find out more about Bear

Everything you need to know about Bear holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bear holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bear holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Bear holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bear. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bear holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bear holiday rentals we have selected for you start as low as AU$193 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Bear rentals

At Expedia, we put the best Bear holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bear rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bear holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bear. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Bear?

Yes, there are holiday rentals in Bear close to Delaware Rock Gym, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Bear. Make sure you have time to check out the football matches while you're in the area.

What are some of the best holiday rentals that Bear has to offer?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Bear is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Bear is House casino.

How many holiday rentals are there in Bear?

Expedia has 7 holiday rentals for your stay in Bear.

What can I see and do in Bear?

Explore the area and family-friendly sights such as Delaware Rock Gym, or get out into nature at a spot like Kirkwood Soccer Complex. While here, Lums Pond State Park and Mansion House Paintball are other places worth a visit.

What are holiday rentals like in Bear?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bear. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for small groups.