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Holiday Homes in Bear

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Bear and around

Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

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

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
The Lodge at Cricklewood...where time melts away....
Dining

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

10.0 out of 10, Exceptional, (73)
"This is a beautiful property and was perfect for our group of 7 friends. The house was spacious and well stocked with a gourmet kitchen and ample indoor and outdoor gathering places. The hot tub was delightful and the owner was responsive to our questions. Highly recommend!"
The Lodge at Cricklewood...where time melts away....
Cozy Farmhouse in Greenville, DE
Fridge, microwave, oven, stovetop

Cozy Farmhouse in Greenville, DE

10.0 out of 10, Exceptional, (24)
"Super clean house that’s perfect for a group gathering "
Cozy Farmhouse in Greenville, DE
Stay & Play at Our Beautiful Retreat
Pool

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Walk to Town & River: Charming Home in North East!
Fridge, microwave, stovetop, dishwasher

Walk to Town & River: Charming Home in North East!

10.0 out of 10, Exceptional, (3)
"Great stay and responsive host. So definitely stay again. "
Walk to Town & River: Charming Home in North East!
Cheerful 3 bedroom home free parking on premise
Fridge, microwave, oven, stovetop

Cheerful 3 bedroom home free parking on premise

8.4 out of 10, Very good, (5)
"Clean and nice house just been better if had a shower area not so good but pay for what you get"
The price is €272
includes taxes & fees
24 Aug - 25 Aug
Cheerful 3 bedroom home free parking on premise
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (179)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Marina

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Homey Retreat in Historic Kennett Square!!
Fridge, microwave, oven, stovetop

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (80)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is €272
includes taxes & fees
18 Aug - 19 Aug
Homey Retreat in Historic Kennett Square!!
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor spa tub

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (49)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay
Private townhouse near downtown and state park
2 bedrooms, WiFi

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is €269
includes taxes & fees
25 Aug - 26 Aug
Private townhouse near downtown and state park
5-bedroom vacation home 5 minutes from historic Charlestown
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is €567
includes taxes & fees
1 Sept - 2 Sept
5-bedroom vacation home 5 minutes from historic Charlestown
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (270)
"Beautiful home and setting!"
Captivating Chesapeake experience
Underground Railroad Barn
Interior

Underground Railroad Barn

9.8 out of 10, Exceptional, (16)
"Great place to stay close to Longwood Gardens. We wanted to visit the Gardens, rated #1 botanical gardens in the United States. The barn was very convenient, spacious, modern. "
The price is €251
includes taxes & fees
17 Aug - 18 Aug
Underground Railroad Barn
Welcome to Woodview Estates!
Interior

Welcome to Woodview Estates!

7.6 out of 10, Good, (4)
"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!
Clean and Cozy 2 BR home blocks away from downtown
Fridge, microwave, oven, stovetop

Clean and Cozy 2 BR home blocks away from downtown

10.0 out of 10, Exceptional, (28)
"Very easy to walk to the downtown area and such a lovely property. Will stay here again if we come back to the North East area"
Clean and Cozy 2 BR home blocks away from downtown
3 Mi to Dtwn: Home w/ Yard in Newark
Fridge, microwave, stovetop, dishwasher

3 Mi to Dtwn: Home w/ Yard in Newark

9.2 out of 10, Wonderful, (9)
"We loved staying here, location is great!"
3 Mi to Dtwn: Home w/ Yard in Newark
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

Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

10/10 Excellent
"I stayed 3 nights in August and loved the quiet location, cleanliness, comfortable bed, and location, accessible to businesses and eateries in Newark. I would like to stay there again, especially if UD is not in session, when the surroundings are so quiet."
Cecile 3-night trip
Posted 1 day ago
Baymont by Wyndham Newark at University of Delaware