Bear Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Bear holiday rentals

Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is HK$1,481
HK$1,814 total
includes taxes & fees
1 Jun - 2 Jun
Nature's Haven Tiny Home
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is HK$1,481
HK$1,853 total
includes taxes & fees
1 Jun - 2 Jun
Tiny Home Tranquil Oasis
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is HK$846
HK$2,201 total
includes taxes & fees
11 Jun - 12 Jun
Historic Chesapeake City Stay
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (20 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is HK$1,738
HK$3,970 total
includes taxes & fees
1 Jun - 2 Jun
Thunder Hill Retreat - Spacious/Deck/Hot tub

Stylish Private Suite in the heart of Brandywine Valley

Stylish Private Suite in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (204 reviews)
"Great time and friendly people "
United States
Karl
The price is HK$1,136
HK$1,705 total
includes taxes & fees
2 Jun - 3 Jun
Stylish Private Suite in the heart of Brandywine Valley
Fridge, microwave, oven, stovetop

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is HK$1,058
HK$2,666 total
includes taxes & fees
7 Jun - 8 Jun
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (27 reviews)
"This condo was in a great location and was very clean and nice. Easy access to the beach and local restaurants and shops. "
United States
Peter F.
The price is HK$1,234
HK$1,917 total
includes taxes & fees
1 Jun - 2 Jun
New Construction townhome close to everything downtown w/transparent pricing
Fridge, microwave, oven, stovetop

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.4 out of 10, Very good, (22 reviews)
"Great stay place was very clean very welcoming "
United States
Destiny J.
The price is HK$862
HK$1,473 total
includes taxes & fees
1 Jun - 2 Jun
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Interior

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (35 reviews)
"Loved the location and place was comfortable. Our dogs loved the fenced back yard."
United States
James C.
The price is HK$1,175
HK$2,688 total
includes taxes & fees
11 Jun - 12 Jun
Underground Railroad Barn
Microwave, oven, stovetop, dishwasher

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.4 out of 10, Very good, (19 reviews)
"Our host was very friendly and easy to communicate with! The house was super clean and had everything that we needed. The neighborhood is very nice. We visited Longwood Garden during our stay. It was spectacular! I highly recommend this property!"
United States
Sharon F.
The price is HK$956
HK$3,635 total
includes taxes & fees
7 Jun - 8 Jun
Kennett Square, Near Longwood Gardens & Downtown
Fridge, microwave, oven, stovetop

Blue Lotus, LUXE Cottage, in walkable Kennett Square near Longwood Gardens

Blue Lotus, LUXE Cottage, in walkable Kennett Square near Longwood Gardens
Kennett Square
10.0 out of 10, Exceptional, (3 reviews)
"It was everything we hoped it would be"
United States
Carla H.
The price is HK$1,262
HK$2,518 total
includes taxes & fees
1 Jun - 2 Jun
Blue Lotus, LUXE Cottage, in walkable Kennett Square near Longwood Gardens
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is HK$925
HK$1,617 total
includes taxes & fees
17 Jun - 18 Jun
Amish Countryside Escape at Forest Edge Farm
Smart TV

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$940
HK$1,263 total
includes taxes & fees
1 Jun - 2 Jun
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Dining

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

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (22 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is HK$1,685
HK$2,795 total
includes taxes & fees
30 Jun - 1 Jul
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Shower, hair dryer, towels, soap

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (10 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is HK$1,164
HK$1,616 total
includes taxes & fees
1 Jun - 2 Jun
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Fridge, microwave, oven, dishwasher

Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
9.8 out of 10, Exceptional, (29 reviews)
"Great location and charming farm house!"
United States
Oliver G.
Underground Railroad 4 Bedroom Farmhouse
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"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."
United States
Rees L.
The price is HK$640
HK$1,276 total
includes taxes & fees
2 Jun - 3 Jun
Summer Rustic Camping with AC and King Bed
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
The price is HK$549
HK$872 total
includes taxes & fees
8 Jun - 9 Jun
Country Get Away Studio Apartment
Fridge, microwave, oven, stovetop

Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.
Downtown Wilmington
9.6 out of 10, Exceptional, (18 reviews)
"Comfortable place, wonderful amenities, and a gracious host. "
United States
Donald H.
The price is HK$1,693
HK$2,811 total
includes taxes & fees
2 Jun - 3 Jun
Two-story condo in luxury townhouse. Free parking.
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,425
HK$2,125 total
includes taxes & fees
2 Jun - 3 Jun
Quarry Landing - Center of Town & River View - 3 Bedroom
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

Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

10/10 Excellent
"nice front desk staff and really nice rooms."
Karen 2-night trip
Posted 1 hour ago
Sheraton Suites Wilmington Downtown

Find out more about Bear

Search for holiday rentals in Bear on Expedia! You can easily find your home rentals, villas, holiday apartments in Bear using one of the methods below:

  • View our selection of featured holiday rentals in Bear
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  • Enter your travel dates to view the best deals on holiday rentals in Bear while they last

Look no further and take a look at our great range of rental properties in Bear!

Frequently asked questions

Are there holiday rentals in Bear?

Yes, there are holiday rentals in Bear close to Delaware Rock Gym, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Bear. Make sure you have time to check out the football matches while you're in the area.

What are some of the best holiday rentals that Bear has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Bear is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Bear?

Expedia has 7 holiday rentals for your stay in Bear.

What can I see and do in Bear?

Explore the area and family-friendly sights such as Delaware Rock Gym, or get out into nature at a spot like Kirkwood Soccer Complex. While here, Lums Pond State Park and Mansion House Paintball are other places worth a visit.

What are holiday rentals like in Bear?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bear. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for small groups.