Condo
10.0(251 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
Parking
Pool
Ocean View
Balcony/Terrace
US $202/Night
7 Nights - US $1,413
Delaware Winter Rental
10.0
Bed & Breakfast
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
269.1 ft²
Oceanfront
Breakfast- Parking
- Ocean View
US $244/Night
7 Nights - US $1,707
Bed & Breakfast
10.0(125 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
Kitchen
US $219/Night
7 Nights - US $1,536
Apartment
10.0(205 Reviews)
1 Bedroom
1 Bath
4 Guests
450 ft²
Private Pool- Oceanfront
- Parking
- Pool
US $221/Night
7 Nights - US $1,545
Apartment
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $243/Night
7 Nights - US $1,701
House
10.0(183 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $395/Night
7 Nights - US $2,768
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
721.18 ft²
- Oceanfront
EV Charge Station- Parking
- Ocean View
US $382/Night
7 Nights - US $2,674
Condo
10.0(175 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $264/Night
7 Nights - US $1,849
House
10.0(2 Reviews)
3 Bedrooms
4 Baths
8 Guests
2798.62 ft²
- Parking
- Pool
Spa
View
US $704/Night
7 Nights - US $4,928
Condo
10.0(154 Reviews)
1 Bedroom
1 Bath
3 Guests
800 ft²
- Oceanfront
- Parking
- Pool
- Spa
US $237/Night
7 Nights - US $1,659
Apartment
10.0(2 Reviews)
1 Bedroom
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $200/Night
7 Nights - US $1,400
Apartment
10.0(144 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $212/Night
7 Nights - US $1,484
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
- 2-Night Off Season is Back! 10% Off Season Booking Discount! No Price Increase!
- Guest-Favorite Rehoboth Beach Retreat:10/10 Reviews - Book early!
- New Beautifully Appointed Home Perfect for Large Groups - Dogs Considered
- Unique retreat right on the beach - unwind and reconnect -linens - child items
- Beautiful Beachfront Retreat on Broadkill Beach. Perfect for couples & families.
- 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 7383 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)
4 Bedrooms
3 Baths
8 Guests
2873.96 ft²
- Parking
- Pool
- Balcony/Terrace
Internet
US $695/Night
7 Nights - US $4,865
Condo
10.0(141 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $189/Night
7 Nights - US $1,323
House
10.0(124 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $265/Night
7 Nights - US $1,858
Cottage
10.0(109 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $336/Night
7 Nights - US $2,352
Cottage
10.0(105 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $417/Night
7 Nights - US $2,916
House
10.0(91 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
Air Conditioner- Internet
US $191/Night
7 Nights - US $1,334
Apartment
10.0(89 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $424/Night
7 Nights - US $2,966
House
10.0(86 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $313/Night
7 Nights - US $2,188
House
10.0(82 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $367/Night
7 Nights - US $2,572
Condo
10.0(81 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $268/Night
7 Nights - US $1,876
Condo
10.0(79 Reviews)
2 Bedrooms
1 Bath
6 Guests
742 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,167
Condo
10.0(77 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $421/Night
7 Nights - US $2,950
