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)
The price is NZ$200
includes taxes & fees
14 Dec - 15 Dec
Cozy loft above ink shop

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 NZ$623
includes taxes & fees
14 Dec - 15 Dec
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is NZ$736
includes taxes & fees
15 Dec - 16 Dec
Thunder Hill Retreat - Spacious/Deck/Hot tub

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (22)
"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 NZ$313
includes taxes & fees
17 Dec - 18 Dec
New Construction townhome close to everything downtown w/transparent pricing

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 NZ$425
includes taxes & fees
16 Dec - 17 Dec
Historic Chesapeake City Stay

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, (3)
"Enjoyed our stay."
United States
Erik H.
The price is NZ$465
includes taxes & fees
5 Jan - 6 Jan 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

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, (7)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is NZ$277
includes taxes & fees
14 Dec - 15 Dec
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Welcome to the Mushroom Capital of the World!

Welcome to the Mushroom Capital of the World!
Kennett Square
10.0 out of 10, Exceptional, (11)
"Loved the property, had everything we needed and more.Plush towels, comfortable bed, wonderful environment filled with really cool art. "
United States
Valerie H.
The price is NZ$286
includes taxes & fees
9 Jan - 10 Jan 2026
Welcome to the Mushroom Capital of the World!

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 NZ$577
includes taxes & fees
14 Dec - 15 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.8 out of 10, Excellent, (13)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is NZ$299
includes taxes & fees
14 Dec - 15 Dec
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington 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 NZ$342
includes taxes & fees
14 Dec - 15 Dec
Stylish Private Suite in the heart of Brandywine Valley

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 NZ$192
includes taxes & fees
22 Dec - 23 Dec
Country Get Away 1 Bedroom Apartment

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 NZ$604
includes taxes & fees
14 Dec - 15 Dec
Amazing Modern house with a full kitchen and parking

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is NZ$394
includes taxes & fees
5 Jan - 6 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom

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 NZ$611
includes taxes & fees
15 Dec - 16 Dec
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens

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
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is NZ$586
includes taxes & fees
14 Dec - 15 Dec
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
10.0 out of 10, Exceptional, (66)
"Comfy, clean and comfortable. Would stay here again. Great location, location, location."
United States
Stephen D.
The price is NZ$578
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Spring House in Gorgeous Chadds Ford!

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.0 out of 10, Very good, (15)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is NZ$829
includes taxes & fees
4 Jan - 5 Jan 2026
Kennett Square, Near Longwood Gardens & Downtown

A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE
Wilmington
The price is NZ$266
includes taxes & fees
14 Dec - 15 Dec
A Cool Place to Stay in Wilmington DE

Charming Carriage House in the Heart of Kennett

Charming Carriage House in the Heart of Kennett
Kennett Square
10.0 out of 10, Exceptional, (37)
"Just what we were hoping for."
United States
Anonymous traveller
The price is NZ$750
includes taxes & fees
14 Dec - 15 Dec
Charming Carriage House in the Heart of Kennett
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 favorite 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 depends 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 NZ$299 per night. Entering your travel dates in the search wizard you might find 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?

Stylish Private Suite in the heart of Brandywine Valley: This holiday home rental outside of Bear offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Mansion House Paintball 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.