A nighttime view of a large suspension bridge with illuminated cables and towers, spanning over a body of water with a cityscape in the background.

Bear Holiday Rentals

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Our top choices for Bear holiday rentals

1. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is NZ$386
includes taxes & fees
14 Sept - 15 Sept
Nature's Haven Tiny Home

2. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is NZ$398
includes taxes & fees
14 Sept - 15 Sept
Tiny Home Tranquil Oasis

3. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is NZ$499
includes taxes & fees
14 Sept - 15 Sept
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

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

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (24 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is NZ$552
includes taxes & fees
24 Aug - 25 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

5. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.0 out of 10, Very good, (18 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is NZ$645
includes taxes & fees
16 Aug - 17 Aug
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

6. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is NZ$340
includes taxes & fees
13 Sept - 14 Sept
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

7. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is NZ$475
includes taxes & fees
16 Aug - 17 Aug
Historic Chesapeake City Stay

8. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is NZ$694
includes taxes & fees
26 Aug - 27 Aug
Elegant Family Stay • Quiet Neighborhood • Comfort

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

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is NZ$622
includes taxes & fees
15 Sept - 16 Sept
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

10. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is NZ$189
includes taxes & fees
10 Sept - 11 Sept
Country Get Away Studio Apartment

11. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
The price is NZ$316
includes taxes & fees
16 Aug - 17 Aug
Cozy Pet Friendly House

12. Perfect for Groups! | Pool + Gym + Free Breakfast

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
The price is NZ$497
includes taxes & fees
13 Sept - 14 Sept
Perfect for Groups! | Pool + Gym + Free Breakfast

13. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is NZ$602
includes taxes & fees
25 Aug - 26 Aug
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

14. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.0 out of 10, Wonderful, (7 reviews)
"We very much enjoyed resting in the house between our activities. The kids loved the large room for watching a soccer match. The dining area is exceptionally nice for kids."
United States
Emily M.
The price is NZ$651
includes taxes & fees
20 Aug - 21 Aug
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

15. Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
The price is NZ$476
includes taxes & fees
17 Aug - 18 Aug
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

16. New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
10.0 out of 10, Exceptional, (1 review)
"If you are visiting the Chase fieldhouse for an event it is 10 minutes driving which is very convenient. The host was very accommodating for what me and my family needed. There was enough space for 5 of us to sleep comfortable."
United States
Alexis O.
The price is NZ$408
includes taxes & fees
17 Aug - 18 Aug
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

17. Entire place with private parking

Entire place with private parking
Hilltop
8.0 out of 10, Very good, (11 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is NZ$264
includes taxes & fees
25 Aug - 26 Aug
Entire place with private parking

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

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is NZ$273
includes taxes & fees
16 Aug - 17 Aug
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

19. Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
The price is NZ$530
includes taxes & fees
9 Sept - 10 Sept
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

20. Private Suite w/sitting room in the heart of Brandywine Valley

Private Suite w/sitting room in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (211 reviews)
"Just perfect !"
United States
Cloudi
The price is NZ$333
includes taxes & fees
14 Sept - 15 Sept
Private Suite w/sitting room in the heart of Brandywine Valley
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bear holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Bear. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Bear. Seeing all the best attractions is bound to make you fall in love with Bear. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Bear short-term rentals, that won’t be hard to do.

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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Bear is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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 1 hot tub.

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 Summit North Marina 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.