Photo by KM Moore

Holiday Homes in Bear

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Featured Holiday Homes in Bear

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!!

Historic Kennett Square

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

The Walton House by RPG

10.0 out of 10, Exceptional, (25)
"The house is beautiful with the perfect mix of historic charm and modern amenities. I am a light sleeper and I liked that the bedrooms seemed to have good blinds. Because it is on a major street, there was some traffic noise. I was able to drown that out with a white noise machine. The beds and pillows were all very comfortable. The only issue I had was on the day of checkout. I wasn't aware that the roads would be shut down for a half marathon. We couldn't leave at the required check-in time. I...
The Walton House by RPG

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
9 Dec - 10 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants

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

Underground Railroad 4 Bedroom Farmhouse

10.0 out of 10, Exceptional, (3)
"The property is very pleasant. The spaces in the farmhouse are all delightful. The owner managed to create a decor that feels both historic, farmhouse while also feeling up-to-date. Just the right amount of elements to make it feel warm and friendly and cozy without the feel that you are sleeping in someone else's house. Kitchen is very functional. Owner provides a keurig, teas, cold water and seltzer. The property is adjacent to a townhouse development. The rear windows of the townhouses...
The price is AU$631
includes taxes & fees
10 Dec - 11 Dec
Underground Railroad 4 Bedroom Farmhouse

Ultimate Retreat @ Papermill Rd

8.8 out of 10, Excellent, (5)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd

Charming Kennett Square Retreat Historic Downtown

9.8 out of 10, Exceptional, (8)
"Clean, ready, host good communications. We had a great visit in Kennett Square. Wish we could have visited a mushroom farm. Nixon park is lovely with easy walking trails. Street parking was convenient, right in front! Lots and of police looking to write tickets. 25 mph is strictly enforced. Thanks"
Charming Kennett Square Retreat Historic Downtown

Sweet Little Home Away From Home, North East, MD

10.0 out of 10, Exceptional, (4)
"My family enjoyed our stay at Angela's house in North East. The house was clean, beds were comfortable, kitchen had what we needed. We'd stay there again."
Sweet Little Home Away From Home, North East, MD

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

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook

Welcome to Woodview Estates!

8.0 out of 10, Very good, (3)
"The house was perfect for our stay. We were in town for a family event and needed a place for 8 adults and 4 children and this was perfect. Lots of space to spread out with a great rec room that kept both kids and adults entertained during down time. The neighborhood was beautiful and had easy access to area restaurants and shopping. Close to many area attractions. It was the perfect location to have close proximity to points of interest and then return to at end of day to a relaxing...
Welcome to Woodview Estates!

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (18)
"Great value, was a great jumping point for our group, who was here for a wedding"
Wilmington Comfort 4 Min to Riverfront fenced yard

Clean Sanitized upscale suite. One or two beds. Private Bath

9.8 out of 10, Exceptional, (8)
"David did a great job with everything! Everything I needed was available for me"
The price is AU$223
includes taxes & fees
9 Dec - 10 Dec
Clean Sanitized upscale suite. One or two beds. Private Bath

Beautiful Brick-Wall House in Historic Newcastle

7.6 out of 10, Good, (10)
"The location was ideal considering it was located at a reasonable distances to all places I had to go to. Short or moderate drive to about 5 different locations."
Beautiful Brick-Wall House in Historic Newcastle

Convenient, spacious 3BR 2.5BA WITH PARKING

10.0 out of 10, Exceptional, (1)
"Very nice townhouse close to lots of stores and restaurants."
Convenient, spacious 3BR 2.5BA WITH PARKING
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 property types 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!!
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.