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Compare 159 Vacation Homes in Bear with updated reviews, rates, and availability.

Villa with hot tub on Ash Lane
The price is $325
$703 total
includes taxes & fees
Jun 16 - Jun 17
Villa with hot tub on Ash Lane
Newly Renovated 4 bedroom home W/big yard and driveway
2.0 out of 10, (1)
"We pulled up to the neighborhood in the early evening and oh my it was not a safe place. We stayed the first night with few options to leave so late. The kitchen sink hot water was not hot and the dishes were not clean in the cabinets. We witnessed illicit activity on the street outside. Also there was people screaming and shining lights in windows all night. We obviously did not feel safe to stay and left terrified in the morning. Not a place to stay with children or if you value your vehicle...
Newly Renovated 4 bedroom home W/big yard and driveway
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
The price is $127
$321 total
includes taxes & fees
Jun 23 - Jun 24
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
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Water-view cabin on 13 acres with private hot tub & kayaks - dog-friendly
8.0 out of 10, Very Good, (1)
"A little hard to find but once you do a comfortable stay with gorgeous sunrises awaits you. Plenty of room and a wonderful kitchen."
Water-view cabin on 13 acres with private hot tub & kayaks - dog-friendly
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (27)
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (88)
"We always look forward to our stay at "Betsys Place"! Very clean, super comfy beds and lovely spacious backyard to relax in! Well appointed kitchen. Very quiet street, we always rest well here and enjoy our stay. Very close proximity to Fair Hill Natural Resource Area trailheads and stables."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Private townhouse near downtown and state park
10.0 out of 10, Exceptional, (5)
"The home was very clean and smelled nice. Neighbors are very friendly as well!"
The price is $179
$346 total
includes taxes & fees
Jun 10 - Jun 11
Private townhouse near downtown and state park
Historic Kennett Square
9.4 out of 10, Exceptional, (36)
"House was very nice. Close to Longwood and busy noisy road. I had trouble getting information because I did not download VRBO APP, also had trouble with door lock, instructions for door lock did not match the lock on the door. Owner was available and helpful. Beds are very comfortable. Nice place"
Historic Kennett Square
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
8.0 out of 10, Very Good, (6)
"Beautiful house! Large house with plenty of room for everyone! Great deck and basement area. Property Manager was accomodating and professional. Would definitely stay again!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Underground Railroad 4 Bedroom Farmhouse
10.0 out of 10, Exceptional, (1)
"A beautifully restored and updated farmhouse. Many modern amenities. Bonus space in the barn is amazing. Kennett Square town shops & cafes offer fun and sometime surprising browsing. Main feature for us was easy access to Longwood Gardens."
The price is $200
$417 total
includes taxes & fees
Jun 16 - Jun 17
Underground Railroad 4 Bedroom Farmhouse
Amazing Modern house with a full kitchen and parking
10.0 out of 10, Exceptional, (1)
"For what and where I needed"
Amazing Modern house with a full kitchen and parking
Waterfront House on the Upper Chesapeake Bay
10.0 out of 10, Exceptional, (1)
"We had a wonderful time at your place. We were celebrating my birthday and was looking for somewhere peaceful and relaxing to unwind. The house is convenient and close to restaurants. I fished while my wife read a book while looking at the awesome view of the water. Thank you for letting us stay at your home."
Waterfront House on the Upper Chesapeake Bay
The Lodge at Cricklewood...where time melts away....
10.0 out of 10, Exceptional, (57)
"14 of us stayed here for a secluded bachelorette weekend in nature and it was truly a dream come true. The home is beautiful and comfortable for a large group, it didn’t even matter that it rained the entire time! We even canceled some of our day plans to stay and enjoy the house. The only minor down side was the water heater struggled keeping up with 14 woman’s daily hygiene needs. Overall, everything was so wonderful and Eric was very pleasant and accommodating. If you stay here you will never...
The Lodge at Cricklewood...where time melts away....
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (19)
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
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, (34)
"Great view awesome living space and easy access. Thank you."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Cheerful 3 bedroom home free parking on premise
Cheerful 3 bedroom home free parking on premise
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, (154)
"The property was beautiful and just as described. The property managers were quick to respond and very helpful. We truly enjoyed our stay."
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Relaxing 5BR Family Home w/ Fire Pit & Pool Table
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this house. The managers were gracious enough to allow for an early check-in and everything was as mentioned. It really helped to have the house layout on the website description so that we could plan (we had multiple family units). Communication with the managers was fantastic from before booking until after checkout. I'd highly recommend staying at this property."
Relaxing 5BR Family Home w/ Fire Pit & Pool Table
Hidden Gem! - Downtown
2.0 out of 10, (2)
"The property description was misleading and lacked important information about the crime rates in the neighborhood. As we entered the property, empty beer bottles and trash littered the sidewalk. This property was surrounded by abandoned, boarded-up homes. Residents sold and used drugs on the sidewalk as we checked in. The living area had numerous exposed wires and the smoke detector hung by wires from the ceiling. The couch looked recently slept on and was covered in hair and crumbs. Fresh...
Hidden Gem! - Downtown
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
9.8 out of 10, Exceptional, (11)
"We had a great time here. House is beautiful and was very peaceful to be right on the lake!"
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
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See all available properties in Bear
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.

Other property types in Bear

House casino
House casino
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Historic Chesapeake City Stay
8.0 out of 10, Very Good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is $120
$237 total
includes taxes & fees
Jun 13 - Jun 14
Historic Chesapeake City Stay
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.

Bear Vacation Homes information

Number of reviews
412
Accommodation
159 Vacation Homes
Lowest Price
$127
Highest Price
$325

Recent reviews of Bear hotels
Expedia verified reviews