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Bear Holiday Rentals

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Our top choices for Bear holiday 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 AU$176
includes taxes & fees
11 Jan - 12 Jan 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 AU$506
includes taxes & fees
12 Jan - 13 Jan 2026
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 AU$536
includes taxes & fees
12 Jan - 13 Jan 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 AU$504
includes taxes & fees
14 Jan - 15 Jan 2026
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 AU$544
includes taxes & fees
11 Jan - 12 Jan 2026
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
9.6 out of 10, Exceptional, (5)
"Enjoyed our stay."
United States
Erik H.
The price is AU$416
includes taxes & fees
6 Jan - 7 Jan 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 AU$540
includes taxes & fees
8 Jan - 9 Jan 2026
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 AU$572
includes taxes & fees
1 Jan - 2 Jan 2026
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 AU$518
includes taxes & fees
4 Jan - 5 Jan 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 AU$244
includes taxes & fees
3 Jan - 4 Jan 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 AU$169
includes taxes & fees
13 Jan - 14 Jan 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 AU$229
includes taxes & fees
5 Jan - 6 Jan 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 AU$598
includes taxes & fees
1 Jan - 2 Jan 2026
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 AU$867
includes taxes & fees
11 Jan - 12 Jan 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 AU$421
includes taxes & fees
8 Jan - 9 Jan 2026
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 AU$428
includes taxes & fees
1 Jan - 2 Jan 2026
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 AU$380
includes taxes & fees
4 Jan - 5 Jan 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 AU$302
includes taxes & fees
2 Jan - 3 Jan 2026
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 AU$389
includes taxes & fees
12 Jan - 13 Jan 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 traveller
The price is AU$578
includes taxes & fees
1 Jan - 2 Jan 2026
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.
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Top Bear Hotel Reviews

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 favourite 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 depend 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 AU$176 per night. Entering your travel dates in the search wizard might find you 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?

The Lodge at Cricklewood...where time melts away....: This holiday home rental outside of Bear is located on a river, and has a fireplace, a balcony 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Bear?

Expedia has 8 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.