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

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
$225 nightly
The price is $234
Sep 23 - Sep 24
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.
$233 nightly
The price is $242
Sep 23 - Sep 24
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
10.0 out of 10, Exceptional, (5 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
$271 nightly
The price is $282
Sep 24 - Sep 25
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.
$384 nightly
The price is $392
Sep 27 - Sep 28
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.
$244 nightly
The price is $269
Sep 27 - Sep 28
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.
$351 nightly
The price is $363
Sep 28 - Sep 29
Total with taxes and fees
Elegant Family Stay • Quiet Neighborhood • Comfort
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
$255 nightly
The price is $281
Sep 27 - Sep 28
Total with taxes and fees
Perfect for Groups! | Pool + Gym + Free Breakfast
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

8. Cozy Comfy Pet Friendly House in a Quiet Neighborhood

Cozy Comfy Pet Friendly House in a Quiet Neighborhood
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.
$193 nightly
The price is $200
Sep 23 - Sep 24
Total with taxes and fees
Cozy Comfy Pet Friendly House in a Quiet Neighborhood
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

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, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
$417 nightly
The price is $417
Oct 21 - Oct 22
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$168 nightly
The price is $185
Sep 27 - Sep 28
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
A wooden cabin with a porch, surrounded by dense forest.

11. 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
Sep 29 - Sep 30
Total with taxes and fees
Country Get Away Studio Apartment
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

12. Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Elkton
10.0 out of 10, Exceptional, (15 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
$1,462 nightly
The price is $1,473
Sep 23 - Sep 24
Total with taxes and fees
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

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
9.8 out of 10, Exceptional, (6 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$358 nightly
The price is $380
Sep 23 - Sep 24
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

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
9.2 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.
$403 nightly
The price is $412
Sep 27 - Sep 28
Total with taxes and fees
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A room with a bed, a wooden door, a patterned rug, and a mirror.

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

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
$286 nightly
The price is $315
Sep 23 - Sep 24
Total with taxes and fees
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
A garden with a fountain, surrounded by lush greenery and flowering plants.

16. 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.
$194 nightly
The price is $200
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.

17. 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.
$263 nightly
The price is $279
Sep 23 - Sep 24
Total with taxes and fees
Historic Chesapeake City Stay
A room with a bed, a dresser, a window with curtains, and an air conditioning unit.

18. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
$335 nightly
The price is $355
Sep 23 - Sep 24
Total with taxes and fees
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

19. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$396 nightly
The price is $420
Oct 5 - Oct 6
Total with taxes and fees
Bohemia Manor Farm
A two-story house with a deck, a barbecue grill, and a covered patio area.

20. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
$448 nightly
The price is $495
Sep 24 - Sep 25
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
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

Super 8 by Wyndham Pennsville/Wilmington

Super 8 by Wyndham Pennsville/Wilmington

8/10 Good
"Room was very clean staff was welcoming."
Glenn 1-night trip
Posted less than an hour ago
Super 8 by Wyndham Pennsville/Wilmington

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, Lums Pond State Park and Summit North Marina 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.