Photo by KM Moore

Bear Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Bear

Our top choices for Bear holiday rentals

Tiny Home Tranquil Oasis

The price is NZ$410
includes taxes & fees
2 Sept - 3 Sept
Tiny Home Tranquil Oasis

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (3)
"Enjoyed"
The price is NZ$401
includes taxes & fees
2 Sept - 3 Sept
Nature's Haven Tiny Home

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

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

8.6 out of 10, Excellent, (7)
"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. "
The price is NZ$317
includes taxes & fees
2 Sept - 3 Sept
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
The price is NZ$534
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom cabin close to Fair Hill on horse farm

Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

9.8 out of 10, Exceptional, (39)
"We had a great stay at this house while in town to celebrate our aunt's 90th birthday. The property was big enough to accommodate our 16 family members and we loved the historic charm. The busy road was a bit noisy but overall we had a wonderful time - thank you Vicki for a great experience!"
The price is NZ$2,907
includes taxes & fees
3 Sept - 4 Sept
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (1)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Luxurious 5-bedroom 5.5 bath house with AC, WiFi in charming Chadds Ford

10.0 out of 10, Exceptional, (2)
"First, communication with the Property Manager was timely, professional, thorough and appreciated!Second, the home was beautiful inside and outside with great space to spend time together,Third, the location was incredible with privacy, beauty and easy proximity to area attractions like Longwood Gardens as well as outstanding restaurants and stores for necessities.Thank you for a home that was perfect for our visit and we hope to visit again soon!"
Luxurious 5-bedroom 5.5 bath house with AC, WiFi in charming Chadds Ford

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (61)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (8)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (52)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (13)
"Always a nice get away…."
The price is NZ$473
includes taxes & fees
2 Sept - 3 Sept
Historic Chesapeake City Stay

Welcome to the Mushroom Capital of the World!

9.8 out of 10, Exceptional, (8)
"The house had everything we needed in the kitchen to make and reheat meals, and the bed was comfortable and could be separated from the living area by a sliding door. We also liked the artistic decor!"
The price is NZ$255
includes taxes & fees
2 Sept - 3 Sept
Welcome to the Mushroom Capital of the World!

Stylish Private Suite in the heart of Brandywine Valley

10.0 out of 10, Exceptional, (186)
"The property was clean and comfortable."
The price is NZ$339
includes taxes & fees
2 Sept - 3 Sept
Stylish Private Suite in the heart of Brandywine Valley

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (40)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is NZ$1,034
includes taxes & fees
2 Sept - 3 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Easy check in process. House very clean. Going location. "
Chesapeake Bay House with Dock & Private Beach

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (31)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

10.0 out of 10, Exceptional, (1)
"The property is exactly as you see in the pictures/description. We were 4 adults, 4 kids (9 months to 13 years). Plenty of room for all of us. Hosts were quick to respond to any messages sent.Had a great 3 days here."
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bear Hotel Reviews

Find out more about Bear

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 favorite 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 depends 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 NZ$255 per night. Entering your travel dates in the search wizard you might find 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.

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.