Bear Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Bear vacation rentals

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.6 out of 10, Exceptional, (5)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is ¥14,404
¥18,184 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy loft above ink shop

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is ¥28,183
¥52,445 total
includes taxes & fees
Dec 30 - Dec 31
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

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

Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
Kennett Square
10.0 out of 10, Exceptional, (35)
"They had everything you may need there just in case and a great location. Beautiful place to stay!"
United States
William R.
The price is ¥28,887
¥55,917 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens

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, (21)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is ¥30,719
¥52,456 total
includes taxes & fees
Dec 30 - Dec 31
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.
Downtown Wilmington
9.6 out of 10, Exceptional, (16)
"This is a great place and super conveniently located. We loved all the amenities! Special shout out for the lovely towels! We would definitely stay here again!"
United States
Shelly S.
The price is ¥33,819
¥55,382 total
includes taxes & fees
Dec 30 - Dec 31
Two-story condo in luxury townhouse. Free parking.

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

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
2.0 star property
Newark
10.0 out of 10, Exceptional, (4)
"Enjoyed our stay."
United States
Erik H.
The price is ¥21,982
¥42,962 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is ¥28,183
¥55,598 total
includes taxes & fees
Dec 30 - Dec 31
Amazing Modern house with a full kitchen and parking

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

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
2.0 star property
Trolley Square
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 ¥16,559
¥53,840 total
includes taxes & fees
Dec 30 - Dec 31
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
10.0 out of 10, Exceptional, (69)
"Historic building, all the amenities. Enjoyed the deck. We ubered everywhere and used food delivery, no restaurants in safe walking distance (we did not have a car)."
United States
Marian D.
The price is ¥31,314
¥53,760 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy Spring House in Gorgeous Chadds Ford!

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
2.0 star property
Elkton
9.8 out of 10, Exceptional, (8)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ¥18,788
¥25,226 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is ¥10,960
¥17,426 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Country Get Away 1 Bedroom Apartment

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, (23)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
The price is ¥16,910
¥25,499 total
includes taxes & fees
Jan 8 - Jan 9, 2026
New Construction townhome close to everything downtown w/transparent pricing

Cheerful 3 bedroom home free parking on premise

Cheerful 3 bedroom home free parking on premise
Chester
8.4 out of 10, Very Good, (5)
"The house was nice and clean and was not to far from the college, parking was good and its close to the highway and food"
United States
dachaun w.
The price is ¥34,524
¥61,503 total
includes taxes & fees
Dec 30 - Dec 31
Cheerful 3 bedroom home free parking on premise

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is ¥62,628
¥91,593 total
includes taxes & fees
Jan 5 - Jan 6, 2026
JVA LUXURY HOUSING

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is ¥12,682
¥38,669 total
includes taxes & fees
Dec 30 - Dec 31
Historic Chesapeake City Stay

Private townhouse near downtown and state park

Private townhouse near downtown and state park
Downtown Wilmington
9.4 out of 10, Exceptional, (12)
"Great little spot in a perfect location for us"
United States
j m.
The price is ¥25,223
¥44,364 total
includes taxes & fees
Dec 30 - Dec 31
Private townhouse near downtown and state park

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

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
2.0 star property
Newark
The price is ¥31,511
¥39,361 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Stylish Private Suite in the heart of Brandywine Valley

Stylish Private Suite in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (195)
"Great time and friendly people "
United States
Karl
The price is ¥20,354
¥30,821 total
includes taxes & fees
Dec 30 - Dec 31
Stylish Private Suite in the heart of Brandywine Valley

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is ¥21,920
¥40,330 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Private 3 room Queen Suite w/Kitchenette

3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome

3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome
Elkton
10.0 out of 10, Exceptional, (1)
"Yes. Very welcoming. Great location. Overall good "
United States
Anonymous traveler
The price is ¥42,274
¥60,411 total
includes taxes & fees
Dec 30 - Dec 31
3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome
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

Search for holiday rentals in Bear on Expedia! You can easily find your home rentals, villas, holiday apartments in Bear using one of the methods below:

  • View our selection of featured holiday rentals in Bear
  • Use the map to find apartments and other holiday homes in the Bear neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bear while they last

Look no further and take a look at our great range of rental properties in Bear!

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?

The Lodge at Cricklewood...where time melts away....: This vacation home rental near Bear is located on a river and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Bear?

Expedia has 8 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.