Photo by KM Moore

Bear Holiday Rentals

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Holiday Rentals in Bear

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Cozy Spring House in Gorgeous Chadds Ford!

10.0 out of 10, Exceptional, (53)
"This cozy Spring House Cottage was the perfect romantic getaway for me and my wife. The cottage was quaint, rustic, very comfortable and very easy to find. We were visiting friends nearby and wanted a local hopping off spot to visit the Brandywine River Museum. Our host was very helpful and easy to communicate with. A delightful find !"
The price is AU$505
includes taxes & fees
1 Dec - 2 Dec
Cozy Spring House in Gorgeous Chadds Ford!

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (54)
"We were relaxing and visiting Mt. Cuba. Wanted to stay in-town. House was adorable and location was great. Lots of nice touches to make everything comfortable (tea, extra blankets, multiple keys). Would absolutely come back!"
The price is AU$610
includes taxes & fees
29 Nov - 30 Nov
Homey Retreat in Historic Kennett Square!!

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Historic Kennett Square

9.4 out of 10, Exceptional, (40)
"Cute and cozy home, Host is a great communicator. "
Historic Kennett Square

Convinient location, Remodel Apartment

10.0 out of 10, Exceptional, (9)
"Well maintained. Great management."
Convinient location, Remodel Apartment

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (28)
"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...
Beachfront Sunsets on the Water at Oakwood Beach

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"This cottage was very cute inside, but could use some curb appeal. When we pulled up, we were worried what the inside looked like. The front bedroom is literally in front of the door, so no one wanted to sleep in that room. The back bedroom in the sunroom, got very cold. The front door would not properly lock, and we realized that you could punch in any number to unlock it. The inside was very cute and updated, but there needs to be some repairs to justify the price. Bedroom doors did not shut...
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AU$717
includes taxes & fees
11 Dec - 12 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (10)
"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."
Stunning waterfront villa with indoor pool and kids swing set and play area.

Beautiful Colonial Style Home in Nottingham PA

9.8 out of 10, Exceptional, (6)
"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."
Beautiful Colonial Style Home in Nottingham PA

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AU$790
includes taxes & fees
11 Dec - 12 Dec
Historic Chesapeake City Stay

Stylish Private Suite in the heart of Brandywine Valley

10.0 out of 10, Exceptional, (167)
"This property is quite simply a 10 out of 10"
The price is AU$302
includes taxes & fees
11 Dec - 12 Dec
Stylish Private Suite in the heart of Brandywine Valley

The Lodge at Cricklewood...where time melts away....

10.0 out of 10, Exceptional, (63)
"Everyone in our group thought the house was great and everyone was very comfortable at all times. It was lovely gathering together on the deck around the fire and inside at the fireplace, and there was never ending entertainment for the kids. The big trees, falling leaves and autumn foliage were a beautiful backdrop. Our time together here will be a new happy memory for all of us. "
The Lodge at Cricklewood...where time melts away....

Cheerful 3 bedroom home free parking on premise

10.0 out of 10, Exceptional, (1)
"Clean and nice house just been better if had a shower area not so good but pay for what you get"
Cheerful 3 bedroom home free parking on premise

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (59)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River
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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Other types of properties in Bear you may be interested in

Best Western Plus Newark/Christiana Inn

2.5 star property
7.0 out of 10, Good, (1100)
"This place was decent for the price! A little noisy, and I had a bug in my room, but it was clean and the staff was excellent."
The price is AU$145
includes taxes & fees
4 Dec - 5 Dec
Best Western Plus Newark/Christiana Inn

Sonesta Select Newark Christiana Mall

3.0 star property
7.8 out of 10, Good, (1082)
"Great people "
The price is AU$169
includes taxes & fees
11 Dec - 12 Dec
Sonesta Select Newark Christiana Mall

Fairfield Inn by Marriott Kennett Square Brandywine Valley

2.5 star property
8.8 out of 10, Excellent, (1049)
"So friendly and breakfast and room great "
The price is AU$216
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn by Marriott Kennett Square Brandywine Valley
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 6 holiday rentals for your stay in Bear.

What can I see and do in Bear?

Family-friendly attractions include Delaware Rock Gym, whereas Lums Pond State Park is a spot to enjoy the outdoors. In the wider area, you’ll find Mansion House Paintball and Kirkwood Soccer Complex.

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.