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Holiday Homes in Bear

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Bear

The Lodge at Cricklewood...where time melts away....
Enjoy cooking in this well-equipped kitchen with a granite countertop, microwave, oven, and ample kitchenware.

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....
Chesapeake Bay House with Dock & Private Beach
Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

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
Stylish Private Suite in the heart of Brandywine Valley
Experience tranquility by the river, surrounded by lush greenery and a historic stone building.

Stylish Private Suite in the heart of Brandywine Valley

10.0 out of 10, Exceptional, (184)
"The property was clean and comfortable."
The price is AU$311
includes taxes & fees
12 Aug - 13 Aug
Stylish Private Suite in the heart of Brandywine Valley
Nancy’s Touch, A Waterfront Paradise!
Stroll through the serene garden, featuring a picturesque arborway, vibrant flowers, and a birdhouse, surrounded by a tranquil body of water.

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (165)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!
Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer
Relax by the pool surrounded by lush greenery and comfortable wicker furniture.

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

10.0 out of 10, Exceptional, (1)
"Very serene and relaxing safe environment "
Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer
Private townhouse near downtown and state park
Cozy retreat with a comfortable bed, desk, and TV, offering a peaceful atmosphere.

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 AU$476
includes taxes & fees
7 Aug - 8 Aug
Private townhouse near downtown and state park
Underground Railroad 4 Bedroom Farmhouse
Cozy barn-style interior with a high ceiling, wooden beams, and string lights.

Underground Railroad 4 Bedroom Farmhouse

9.8 out of 10, Exceptional, (20)
"Great property for a girls' weekend. Super clean, helpful and friendly owner, cute property and grounds, well-maintained."
The price is AU$591
includes taxes & fees
17 Aug - 18 Aug
Underground Railroad 4 Bedroom Farmhouse
Ultimate Retreat @ Papermill Rd
Equipped with a microwave, oven, and dishwasher, this kitchen offers a window for natural light and a clean, contemporary design.

Ultimate Retreat @ Papermill Rd

9.2 out of 10, Wonderful, (7)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Relax in this stylish living space with a flat-screen TV and comfortable couch.

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (18)
"We rented this townhouse for a month for my son's surgical residency rotation at Cristiana Care. It was a perfect location and easy to get to and from the hospital. Owner was very responsive with any questions / concerns which we appreciated. Very quiet and close to grocery stores. Even had a Trader Joe's close by!"
The price is AU$554
includes taxes & fees
11 Aug - 12 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

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
The Historic Walton House by RPG
Enjoy cooking in this well-equipped kitchen with a gas stove, double oven, and microwave.

The Historic Walton House by RPG

10.0 out of 10, Exceptional, (34)
"I couldn’t rate our stay any higher! The property, the location, the communication were all subperb. I would stay here again and again. "
The price is AU$1,083
includes taxes & fees
7 Aug - 8 Aug
The Historic Walton House by RPG
Captivating Chesapeake experience
Relax on the pier with a view of distant landforms.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (269)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience
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, (2)
"Great stay and responsive host. So definitely stay again. "
Walk to Town & River: Charming Home in North East!
Kennett Square, Near Longwood Gardens & Downtown
Relax in this stylish living room with a sectional sofa, flat-screen TV, and decorative plant.

Kennett Square, Near Longwood Gardens & Downtown

8.0 out of 10, Very good, (13)
"We had a good time."
The price is AU$772
includes taxes & fees
19 Aug - 20 Aug
Kennett Square, Near Longwood Gardens & Downtown
Underground Railroad Barn
Cozy barn-style interior with a high ceiling and large arched window.

Underground Railroad Barn

9.8 out of 10, Exceptional, (15)
"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 AU$440
includes taxes & fees
13 Aug - 14 Aug
Underground Railroad Barn
Luxury 2-bedroom house with Water views, Chesapeake City
Enjoy a scenic view of the lake from this kitchen, featuring a large window and stainless steel appliances.

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "
Luxury 2-bedroom house with Water views, Chesapeake City
3 Mi to Dtwn: Home w/ Yard in Newark
Enjoy cooking in this well-equipped kitchen with a stainless steel oven, microwave, and sink.

3 Mi to Dtwn: Home w/ Yard in Newark

9.6 out of 10, Exceptional, (8)
"We loved staying here, location is great!"
3 Mi to Dtwn: Home w/ Yard in Newark
Wilmington Comfort 4 Min to Riverfront fenced yard
Kitchen features a refrigerator, oven, and microwave, with a window offering a view.

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (20)
"Good location in downtown Wilmington that works well for a small group looking for a good alternative to nearby Riverfront hotels. "
Wilmington Comfort 4 Min to Riverfront fenced yard
Cheerful 3 bedroom home free parking on premise
Enjoy cooking in this well-equipped kitchen with a stainless steel range hood, microwave, and double sink.

Cheerful 3 bedroom home free parking on premise

8.0 out of 10, Very good, (4)
"The house was nice and clean and was not to far from the college, parking was good and its close to the highway and food"
The price is AU$485
includes taxes & fees
7 Aug - 8 Aug
Cheerful 3 bedroom home free parking on premise
Waterfront house with amazing views. Top of the Chesapeake
Relax on the deck with Adirondack chairs and enjoy the serene lake view.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (99)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake
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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