Photo by KM Moore

Search Vacation Homes in Bear

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Bear

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (261)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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, (18)
"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
*** 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, (173)
"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
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is SAR 1,347
SAR 2,450 total
includes taxes & fees
16 Jul - 17 Jul
5-bedroom vacation home 5 minutes from historic Charlestown
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

2.0 out of 10, (1)
"Never heard from host. Expedia had to cancel reservation."
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Underground Railroad 4 Bedroom Farmhouse
Interior

Underground Railroad 4 Bedroom Farmhouse

9.8 out of 10, Exceptional, (16)
"Had a wonderful stay! Property is beautiful and so well maintained. Very homey! "
The price is SAR 751
SAR 1,547 total
includes taxes & fees
2 Jul - 3 Jul
Underground Railroad 4 Bedroom Farmhouse
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
Interior

Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL

Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun loungers, beach towels

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (97)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

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

9.8 out of 10, Exceptional, (17)
"Wonderful experience, thank you for having us!! "
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Cheerful 3 bedroom home free parking on premise
Fridge, microwave, oven, stovetop

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"
The price is SAR 574
SAR 1,166 total
includes taxes & fees
28 Jun - 29 Jun
Cheerful 3 bedroom home free parking on premise
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds

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

9.4 out of 10, Exceptional, (46)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
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, (56)
"Great place. Accurately depicted in photos. Nice quiet neighborhood. Super dog friendly!"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Private townhouse near downtown and state park
2 bedrooms, WiFi

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (8)
"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 SAR 605
SAR 1,150 total
includes taxes & fees
23 Jun - 24 Jun
Private townhouse near downtown and state park
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
Interior

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

8.4 out of 10, Very Good, (14)
"Amazing stay. nice quiet clean home. Accommodating for the whole family. Host was easy to connect with very helpful loved our stay ! Looking forward to booking again."
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Living area

Cozy on the Hill. Close to Riverfront, Brandywine park and great food

9.6 out of 10, Exceptional, (14)
"Perfect place to stay for an extended work trip. The host is responsive, accommodating and was great to work with. "
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Spacious North East Home w/ Fenced Yard & Fire Pit
Terrace/patio

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (8)
"Was the best option in the area and would use again."
Spacious North East Home w/ Fenced Yard & Fire Pit
Summer Rustic Camping with AC and King Bed
Miscellaneous

Summer Rustic Camping with AC and King Bed

10.0 out of 10, Exceptional, (3)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is SAR 345
SAR 650 total
includes taxes & fees
22 Jun - 23 Jun
Summer Rustic Camping with AC and King Bed
Luxury 2-bedroom house with Water views, Chesapeake City
Fridge, microwave, oven, stovetop

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
Luxury 2-bedroom house with Water views, Chesapeake City
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

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free