A nighttime view of a large suspension bridge with illuminated cables and towers, spanning over a body of water with a cityscape in the background.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Bear holiday homes

A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

1. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.0 out of 10, Very good, (20 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is £309
includes taxes & fees
4 Oct - 5 Oct
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

2. Cozy Comfy Pet Friendly House in a Quiet Neighborhood

Cozy Comfy Pet Friendly House in a Quiet Neighborhood
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."
United States
Chris D.
The price is £143
includes taxes & fees
1 Oct - 2 Oct
Cozy Comfy Pet Friendly House in a Quiet Neighborhood
A two-story residential building with a stone facade, a large front lawn, and a driveway.

3. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is £280
includes taxes & fees
28 Sept - 29 Sept
Elegant Family Stay • Quiet Neighborhood • Comfort
A garden with a fountain, surrounded by lush greenery and flowering plants.

4. 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, (29 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is £154
includes taxes & fees
27 Sept - 28 Sept
New Construction townhome close to everything downtown w/transparent pricing
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

5. 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
9.8 out of 10, Exceptional, (6 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is £288
includes taxes & fees
29 Sept - 30 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

6. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.2 out of 10, Wonderful, (9 reviews)
"Comfy cozy… home away from home. Location was perfectly centered for the activities we did and the restaurants we chose. Beds and sheets were great and plenty of hot water. We had a nice relaxing stay."
United States
carla k.
The price is £301
includes taxes & fees
27 Sept - 28 Sept
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A room with a bed, a dresser, a window with curtains, and an air conditioning unit.

7. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
The price is £251
includes taxes & fees
1 Oct - 2 Oct
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

8. Private Suite w/sitting room in the heart of Brandywine Valley

Private Suite w/sitting room in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (213 reviews)
"Just perfect !"
United States
Cloudi
The price is £156
includes taxes & fees
1 Oct - 2 Oct
Private Suite w/sitting room in the heart of Brandywine Valley
A rustic barn interior with wooden beams, a large window, and string lights.

9. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
10.0 out of 10, Exceptional, (42 reviews)
"Very cool place! "
United States
Scott M.
The price is £246
includes taxes & fees
27 Sept - 28 Sept
Underground Railroad Barn
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

10. Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (22 reviews)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is £348
includes taxes & fees
6 Oct - 7 Oct
Kennett Square, Near Longwood Gardens & Downtown
A modern living room with a grey sofa, a round coffee table, and a large horse painting on the wall.

11. New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
10.0 out of 10, Exceptional, (2 reviews)
"If you are visiting the Chase fieldhouse for an event it is 10 minutes driving which is very convenient. The host was very accommodating for what me and my family needed. There was enough space for 5 of us to sleep comfortable."
United States
Alexis O.
The price is £164
includes taxes & fees
5 Oct - 6 Oct
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
A modern kitchen with a central island, bar stools, wooden cabinets, and a large window.

12. Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
10.0 out of 10, Exceptional, (34 reviews)
"Comfortable, clean, thoughtfully stocked property. We would definitely stay again!"
United States
Amy Y.
The price is £216
includes taxes & fees
7 Oct - 8 Oct
Underground Railroad 4 Bedroom Farmhouse
A single-story house with a front porch, a small garden, and a clear sky.

13. Cottage 3BR Near Longwood Gardens

Cottage 3BR Near Longwood Gardens
Avondale
The price is £283
includes taxes & fees
29 Sept - 30 Sept
Cottage 3BR Near Longwood Gardens
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

14. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 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 £177
includes taxes & fees
12 Oct - 13 Oct
Amish Countryside Escape at Forest Edge Farm
A kitchen with white cabinets, a dishwasher, a window with a view of greenery, and a door with a glass panel.

15. Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking

Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
Wilmington
10.0 out of 10, Exceptional, (3 reviews)
"Thank you for a lovely stay. Loved the reading nook. Plenty of space in this quiet, yet convenient neighborhood."
United States
Alan B.
The price is £278
includes taxes & fees
28 Sept - 29 Sept
Entire Private Wilmington Home | Sleeps 6 | 2 Baths & Parking
A dining area with a white table, wicker chairs, a ceiling fan, and wall-mounted light fixtures.

16. SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome

SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
Kennett Square
10.0 out of 10, Exceptional, (7 reviews)
"The home was very clean and perfectly situated for easy access to downtown and local sites."
United States
Patricia Nora R.
The price is £339
includes taxes & fees
1 Oct - 2 Oct
SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
A modern kitchen with a black and white herringbone backsplash, stainless steel appliances, and a window with a view.

17. Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!
Kennett Square
10.0 out of 10, Exceptional, (108 reviews)
"The property was wonderful...outdoor seating was a plus...the house was clean and the host was attentive. Close to restaurants, a true gem in Kennett square."
United States
Melissa K.
The price is £275
includes taxes & fees
28 Sept - 29 Sept
Homey Retreat in Historic Kennett Square!!

18. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (13 reviews)
"This is our 3rd year in a row renting Jessica’s property. We truly enjoyed our stay. Highly recommend staying here. Beautiful backyard looking out to the bay! It has been a highlight staying here visiting for UD graduations. We hope to be back!"
United States
Natasha G.
The price is £343
includes taxes & fees
4 Oct - 5 Oct
Sunset River Shack -amazing waterfront view
A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

19. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is £277
includes taxes & fees
7 Oct - 8 Oct
Bohemia Manor Farm
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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