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 Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Bear vacation rentals

A covered deck area with a grill and outdoor seating.

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
$219 nightly
The price is $228
Sep 27 - Sep 28
Total with taxes and fees
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.
$224 nightly
The price is $233
Sep 27 - Sep 28
Total with taxes and fees
Tiny Home Tranquil Oasis
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

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
9.8 out of 10, Exceptional, (6 reviews)
"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...
United States
Karen
$270 nightly
The price is $281
Sep 29 - Sep 30
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

4. 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, (20 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
$377 nightly
The price is $385
Sep 28 - Sep 29
Total with taxes and fees
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
10.0 out of 10, Exceptional, (1 review)
"Clean rooms close to all things we needed breakfast was good and plentiful wish the afternoon buffet was available would use this place again"
United States
Susan H.
$229 nightly
The price is $252
Oct 25 - Oct 26
Total with taxes and fees
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
A two-story residential building with a stone facade, a large front lawn, and a driveway.

6. 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.
$322 nightly
The price is $333
Sep 28 - Sep 29
Total with taxes and fees
Elegant Family Stay • Quiet Neighborhood • Comfort
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

7. 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, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
$355 nightly
The price is $355
Oct 26 - Oct 27
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

8. Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."
United States
Chris D.
$189 nightly
The price is $196
Oct 1 - Oct 2
Total with taxes and fees
Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$167 nightly
The price is $183
Oct 4 - Oct 5
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
A garden with a fountain, surrounded by lush greenery and flowering plants.

10. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
$192 nightly
The price is $198
Sep 27 - Sep 28
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
A riverside dock with boats, a covered seating area, and a bridge in the background.

11. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 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.
$253 nightly
The price is $268
Sep 27 - Sep 28
Total with taxes and fees
Historic Chesapeake City Stay
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

12. 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
9.2 out of 10, Wonderful, (9 reviews)
"Comfy cozy… home away from home. Location was perfectly centered for the activities we did and the restaurants we chose. Beds and sheets were great and plenty of hot water. We had a nice relaxing stay."
United States
carla k.
$380 nightly
The price is $389
Sep 27 - Sep 28
Total with taxes and fees
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
$239 nightly
The price is $263
Oct 25 - Oct 26
Total with taxes and fees
Perfect for Groups! | Pool + Gym + Free Breakfast
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

14. 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
9.8 out of 10, Exceptional, (6 reviews)
"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"
United States
Shana G.
$322 nightly
The price is $342
Sep 29 - Sep 30
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

15. 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, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Sep 27 - Sep 28
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

16. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (1 review)
$171 nightly
The price is $189
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom apartment in Lincoln University
A wooden cabin with a porch, surrounded by dense forest.

17. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Oct 5 - Oct 6
Total with taxes and fees
Country Get Away Studio Apartment
A bunk bed room with white bedding and blue throw blankets.

18. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$335 nightly
The price is $356
Oct 18 - Oct 19
Total with taxes and fees
Bohemia Manor Farm
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

19. 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, (213 reviews)
"Just perfect !"
United States
Cloudi
$205 nightly
The price is $212
Oct 1 - Oct 2
Total with taxes and fees
Private Suite w/sitting room in the heart of Brandywine Valley
A modern living room with a grey sofa, a round coffee table, and a large horse painting on the wall.

20. 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, (3 reviews)
"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.
$206 nightly
The price is $212
Sep 27 - Sep 28
Total with taxes and fees
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
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

SureStay Plus Hotel by Best Western Brandywine Valley

SureStay Plus Hotel by Best Western Brandywine Valley

10/10 Excellent
"We were in town for the HORROR FEST FILM FESTIVAL. Check-in was super easy and the staff was delightful. Our room was very clean, well prepped, and slept well. The only dislike was the loud neighbor, but I will not hold that against the place. The breakfast was great and filling, lots of options. Definitely recommend for anyone traveling though. Great shampoo provided. Good prices, and an actual modern tv that was nice to relax watching during the stay."
Tyler 1-night trip
Posted 2 hours ago
SureStay Plus Hotel by Best Western Brandywine Valley

Find out more about Bear

Everything you need to know about Bear vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bear vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bear vacation 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 low season months. For more hustle and bustle, you may prefer to visit Bear in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bear rentals

At Expedia, we put the best Bear vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Bear?

Yes, you can find vacation rentals in Bear near Delaware Rock Gym, or you can go with a more secluded option if you're looking for extra privacy while you relax. The shops and restaurants are several reasons why visitors like Bear. Make sure you have time to check out the soccer matches while you're in the area.

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

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental near Bear is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Bear?

Expedia has 7 vacation 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, Mansion House Paintball and Lums Pond State Park are other places worth a visit.

What are vacation rentals like in Bear?

Vacation rentals are private properties you can book for a short or long stay in Bear. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.