Delaware Winter Rental
Condo
10.0(245 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
Parking
Pool
Ocean View
Balcony/Terrace
R3,297/Night
7 Nights - R23,085
Bed & Breakfast
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
269.1 ft²
Oceanfront
Breakfast- Parking
- Ocean View
R3,990/Night
7 Nights - R27,928
Bed & Breakfast
10.0(125 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
Kitchen
R3,590/Night
7 Nights - R25,130
House
10.0(174 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
R6,257/Night
7 Nights - R43,798
Apartment
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R3,976/Night
7 Nights - R27,830
Condo
10.0(171 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
Hot Tub- Parking
- Pool
R4,359/Night
7 Nights - R30,513
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
2561.81 ft²
Private Pool- Hot Tub
- Parking
- Pool
R10,209/Night
7 Nights - R71,464
Condo
10.0(153 Reviews)
1 Bedroom
1 Bath
3 Guests
800 ft²
- Oceanfront
- Parking
- Pool
Spa
R3,888/Night
7 Nights - R27,224
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
7 Guests
1819.1 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R6,092/Night
7 Nights - R42,653
Apartment
10.0(144 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R3,486/Night
7 Nights - R24,394
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R13,187/Night
7 Nights - R92,308
House
10.0(122 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R4,285/Night
7 Nights - R30,006
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.
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
Historic District
Selbyville
Dewey Beach
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:
- 30% DISCOUNT FOR THE WEEK OF 5 SEP TO 12SEP Original Beach Styled Cottage
- Beachfront Condo, 1st Floor Ocean View
- Beach Block Townhouse With NEW Everything & Ocean Views ☀️🦀🐬
- In-Town Lewes! Walk to Shops & Dining
- Beautiful Rehoboth beach home - heated pool, 3 blocks to beach!
- 2-Night Off Season is Back! 10% Off Season Booking Discount! No Price Increase!
- Luxury Condo - Family-Friendly - Prime location
- New Beautifully Appointed Home Perfect for Large Groups - Dogs Considered
- A short walk to the beach and town from your secluded home in Bethany Beach.
- Panoramic Oceanfront. Beautiful Five Star. The get-away for any season.
2. How many Winter Rentals are available in Delaware?
Currently, the total number of properties listed by RBO in 2026 is over 7461 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)
3 Bedrooms
4 Baths
8 Guests
2798.62 ft²
- Parking
- Pool
- Spa
View
R11,518/Night
7 Nights - R80,626
Cottage
10.0(107 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
R6,934/Night
7 Nights - R48,542
Cottage
10.0(101 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,833/Night
7 Nights - R47,823
Condo
10.0(101 Reviews)
2 Bedrooms
2 Baths
7 Guests
1421 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R3,872/Night
7 Nights - R27,110
House
10.0(91 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
Air Conditioner
Internet
R3,118/Night
7 Nights - R21,825
Apartment
10.0(85 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,809/Night
7 Nights - R47,659
Condo
10.0(81 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R17,280/Night
7 Nights - R120,955
House
10.0(81 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
R6,138/Night
7 Nights - R42,963
Condo
10.0(81 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R4,344/Night
7 Nights - R30,415
House
10.0(79 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,572/Night
7 Nights - R39,004
Condo
10.0(77 Reviews)
2 Bedrooms
1 Bath
6 Guests
742 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,256/Night
7 Nights - R36,795
House
10.0(77 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R4,292/Night
7 Nights - R30,038
