Bear Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Bear holiday rentals

Fridge, microwave, oven, stovetop
Cozy loft above ink shop

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.6 out of 10, Exceptional, (5)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is HK$716
HK$903 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy loft above ink shop
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is HK$630
HK$1,921 total
includes taxes & fees
29 Dec - 30 Dec
Historic Chesapeake City Stay
1 bedroom, iron/ironing board, free WiFi, bed sheets
Welcome to the Mushroom Capital of the World!

Welcome to the Mushroom Capital of the World!

Welcome to the Mushroom Capital of the World!
Kennett Square
10.0 out of 10, Exceptional, (11)
"Loved the property, had everything we needed and more.Plush towels, comfortable bed, wonderful environment filled with really cool art. "
United States
Valerie H.
The price is HK$654
HK$1,164 total
includes taxes & fees
27 Dec - 28 Dec
Welcome to the Mushroom Capital of the World!
Fridge, microwave, oven, dishwasher
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
2.0 star property
Trolley Square
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is HK$823
HK$2,799 total
includes taxes & fees
25 Dec - 26 Dec
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is HK$544
HK$866 total
includes taxes & fees
31 Dec - 1 Jan 2026
Country Get Away 1 Bedroom Apartment
Stylish Private Suite in the heart of Brandywine Valley

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, (195)
"Great time and friendly people "
United States
Karl
The price is HK$1,011
HK$1,562 total
includes taxes & fees
3 Jan - 4 Jan 2026
Stylish Private Suite in the heart of Brandywine Valley
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.

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.6 out of 10, Excellent, (16)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is HK$770
HK$1,349 total
includes taxes & fees
28 Dec - 29 Dec
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
1 bedroom
Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5)
"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$653
HK$1,284 total
includes taxes & fees
14 Jan - 15 Jan 2026
Summer Rustic Camping with AC and King Bed
Outdoor spa tub
Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is HK$1,348
HK$3,473 total
includes taxes & fees
5 Jan - 6 Jan 2026
Thunder Hill Retreat - Spacious/Deck/Hot tub
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

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
Elkton
9.8 out of 10, Exceptional, (7)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$933
HK$1,253 total
includes taxes & fees
25 Dec - 26 Dec
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Property grounds
New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (23)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
The price is HK$1,113
HK$1,591 total
includes taxes & fees
4 Jan - 5 Jan 2026
New Construction townhome close to everything downtown w/transparent pricing
Terrace/patio
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
2.0 star property
Newark
10.0 out of 10, Exceptional, (4)
"Enjoyed our stay."
United States
Erik H.
The price is HK$1,218
HK$2,283 total
includes taxes & fees
13 Jan - 14 Jan 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Interior
Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.0 out of 10, Very good, (15)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is HK$1,058
HK$3,761 total
includes taxes & fees
2 Jan - 3 Jan 2026
Kennett Square, Near Longwood Gardens & Downtown
Private kitchen
A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE
Wilmington
The price is HK$817
HK$1,203 total
includes taxes & fees
25 Dec - 26 Dec
A Cool Place to Stay in Wilmington DE
Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$1,400
HK$2,762 total
includes taxes & fees
27 Dec - 28 Dec
Amazing Modern house with a full kitchen and parking
Outdoor spa tub
Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!

Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!

Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!
Concordville
The price is HK$1,033
HK$1,301 total
includes taxes & fees
28 Dec - 29 Dec
Free Breakfast. Seasonal Outdoor Pool. Gym. Near Longwood Gardens!
Interior
Underground Railroad Barn

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (29)
"Great little gem! Convenient location and a nice yard for the dog to play."
United States
Joanne S.
The price is HK$972
HK$2,503 total
includes taxes & fees
4 Jan - 5 Jan 2026
Underground Railroad Barn
Private kitchen
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
3.0 star property
Trolley Square
6.0 out of 10, (1)
"Be aware that there is on street parking that requires a permit from the city of Wilmington. Red Awni ng worked with me to resolve the issue but it took some time and a few texts to make it work.The on street parking placed me a block and half from the propery. No cost but need proof of renting the space. The GPS sent you down a one way street that does not bring by the front of the property. This was a problem finding the property after dark. No climate control of the rental unit. The bed was...
United States
Clifford
The price is HK$687
HK$2,195 total
includes taxes & fees
28 Dec - 29 Dec
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

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, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,151
HK$1,797 total
includes taxes & fees
12 Jan - 13 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
2.0 star property
Newark
The price is HK$925
HK$1,182 total
includes taxes & fees
28 Dec - 29 Dec
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
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

Brandywine River Hotel

Brandywine River Hotel

10/10 Excellent
"Very nice hotel. Great location! Customer service was awesome!"
Joanne 1-night trip
Posted 2 days ago
Brandywine River Hotel

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
  • Use the map to find apartments and other holiday homes in the Bear neighbourhood you prefer
  • 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!

Explore a world of travel with Expedia

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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Bear is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.