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 Holiday Rentals

  • 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 holiday rentals

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
The price is NZ$411
includes taxes & fees
1 July - 2 July
Nature's Haven Tiny Home

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is NZ$424
includes taxes & fees
1 July - 2 July
Tiny Home Tranquil Oasis

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
The price is NZ$510
includes taxes & fees
3 July - 4 July
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (23 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is NZ$495
includes taxes & fees
1 July - 2 July
Historic Chesapeake City Stay

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is NZ$197
includes taxes & fees
13 July - 14 July
Country Get Away Studio Apartment

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (37 reviews)
"Very cool place! "
United States
Scott M.
The price is NZ$509
includes taxes & fees
1 July - 2 July
Underground Railroad Barn

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, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is NZ$285
includes taxes & fees
1 July - 2 July
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
9.8 out of 10, Exceptional, (30 reviews)
"Great location and charming farm house!"
United States
Oliver G.
The price is NZ$557
includes taxes & fees
8 July - 9 July
Underground Railroad 4 Bedroom Farmhouse

Overlook Brandywine Valley

Overlook Brandywine Valley
Thornton
10.0 out of 10, Exceptional, (1 review)
"We had a 5 star stay this past weekend as we were in town to see WrestleMania in Philly. It was nice to stay out of the city but somewhere that still was close to everything! Jeff was very kind and was available for any help or questions. We loved the wallpaper and the bed was very comfortable. We plan to come back again!"
New Zealand
Danielle A.
The price is NZ$377
includes taxes & fees
5 July - 6 July
Overlook Brandywine Valley

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, (27 reviews)
"There were 3 of us ladies for the week. Lisa was a great host and recommendations were all perfect. We will definitely be back. Everything was clean and neat. We loved staying there. "
United States
Bonnie W.
The price is NZ$384
includes taxes & fees
6 July - 7 July
New Construction townhome close to everything downtown w/transparent pricing

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, (206 reviews)
"Very convenient to our tour at Winterthur. Clean, quiet and comfortable. Thank you "
United States
Susan M.
The price is NZ$376
includes taxes & fees
12 July - 13 July
Stylish Private Suite in the heart of Brandywine Valley

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (21 reviews)
"Our host was very friendly and easy to communicate with! The house was super clean and had everything that we needed. The neighborhood is very nice. We visited Longwood Garden during our stay. It was spectacular! I highly recommend this property!"
United States
Sharon F.
The price is NZ$821
includes taxes & fees
1 July - 2 July
Kennett Square, Near Longwood Gardens & Downtown

Cozy retreat in Thornton, PA!

Cozy retreat in Thornton, PA!
Thornton
10.0 out of 10, Exceptional, (2 reviews)
"Great, cozy room above a fabulous beerhall in a beautiful area! Host was super helpful throughout our stay! Would definitely stay again!"
United States
Grace F.
The price is NZ$286
includes taxes & fees
7 July - 8 July
Cozy retreat in Thornton, PA!

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, (23 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is NZ$572
includes taxes & fees
6 July - 7 July
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is NZ$598
includes taxes & fees
13 July - 14 July
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (7 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is NZ$325
includes taxes & fees
22 July - 23 July
Summer Rustic Camping with AC and King Bed

Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!

Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!
Concordville
The price is NZ$370
includes taxes & fees
1 July - 2 July
Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (23 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is NZ$929
includes taxes & fees
1 July - 2 July
Thunder Hill Retreat - Spacious/Deck/Hot tub

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

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
The price is NZ$541
includes taxes & fees
1 July - 2 July
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is NZ$514
includes taxes & fees
6 July - 7 July
Private 3 room Queen Suite w/Kitchenette
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

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$376 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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Bear is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.