Delaware Winter Rental
New
House
10.0(16 Reviews)
4 Bedrooms
4 Baths
10 Guests
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
R11,133/Night
7 Nights - R77,929
Bed & Breakfast
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
269.1 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,978/Night
7 Nights - R27,847
Condo
3 Bedrooms
3 Baths
10 Guests
2153 ft²
Private Pool- Oceanfront
Hot Tub
Spa
R5,957/Night
7 Nights - R41,697
New
Condo
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
Pool- Ocean View
R4,353/Night
7 Nights - R30,473
Apartment
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Pool
- Ocean View
View
R3,964/Night
7 Nights - R27,749
House
9 Bedrooms
7 Baths
20 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R33,920/Night
7 Nights - R237,441
House
10.0(4 Reviews)
3 Bedrooms
3 Baths
7 Guests
1819.1 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R4,405/Night
7 Nights - R30,832
New
House
5 Bedrooms
6 Baths
12 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
R25,325/Night
7 Nights - R177,277
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
2561.81 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R10,180/Night
7 Nights - R71,257
House
4 Bedrooms
4 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R20,413/Night
7 Nights - R142,889
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Pool
- Ocean View
- View
R1,958/Night
7 Nights - R13,703
New
House
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R16,395/Night
7 Nights - R114,764
Why Choose Rent By Owner for your Delaware Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Delaware
How to Book Your Delaware Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Delaware
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Delaware, DE
Sussex County
Delaware Beaches
Rehoboth Beach
Bethany Beach
South Rehoboth
Ocean View
Dewey Beach
Selbyville
Historic District
New Castle County
Wilmington
Frequently Asked Questions About Delaware Winter Rentals
1. What are the top Winter Rentals in Delaware?
There are a lot of options in Delaware. If you plan on staying in the Delaware area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Delaware:
- Bayfront Cottage with Spectacular Views
- Original Beach Styled Cottage
- Beachfront Condo, 1st Floor Ocean View
- Beautiful Dog Friendly First Floor Condo Between Lewes and Rehoboth Beach
- Cozy cottage on the Miller farm.
- Beachfront, Oceanfront, Rehoboth, DE on the Boardwalk
- Gather The Family In The Heart Of Rehoboth Beach Accessible
- Fabulous Fenwick Island Waterfront property!
- Broadkill Beach near Lewes Milton Rehoboeth Delaware
- LUXURY CONDO. CLOSE TO BEACH!
2. How many Winter Rentals are available in Delaware?
Currently, the total number of properties listed by RBO in 2026 is over 7670 in the Delaware area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Delaware.
More Rentals You May Like Near Delaware
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R13,149/Night
7 Nights - R92,040
New
Condo
3 Bedrooms
2 Baths
12 Guests
1500 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
R14,533/Night
7 Nights - R101,730
House
6 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Kitchen
R13,513/Night
7 Nights - R94,585
House
5 Bedrooms
4 Baths
11 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R12,786/Night
7 Nights - R89,495
House
5 Bedrooms
5 Baths
11 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R12,081/Night
7 Nights - R84,568
New
House
5 Bedrooms
4 Baths
10 Guests
- Kitchen
Parking- Air Conditioner
- Internet
R10,590/Night
7 Nights - R74,128
House
5 Bedrooms
5 Baths
14 Guests
3000 ft²
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
R10,195/Night
7 Nights - R71,355
House
5 Bedrooms
5 Baths
12 Guests
- Pool
- Kitchen
- Child Friendly
Laundry
R8,968/Night
7 Nights - R62,774
New
Condo
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R8,374/Night
7 Nights - R58,614
New
House
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R8,282/Night
7 Nights - R57,978
New
House
4 Bedrooms
4 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R8,234/Night
7 Nights - R57,635
Condo
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R8,090/Night
7 Nights - R56,624
