Delaware Winter Rental
House
10.0(79 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $708/Night
7 Nights - US $4,955
Bed & Breakfast
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
269.1 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $244/Night
7 Nights - US $1,707
Bed & Breakfast
10.0(122 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Kitchen
US $219/Night
7 Nights - US $1,536
New
House
10.0(65 Reviews)
5 Bedrooms
3 Baths
8 Guests
3000 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
US $582/Night
7 Nights - US $4,073
Apartment
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
Pool- Ocean View
View
US $243/Night
7 Nights - US $1,701
House
10.0(58 Reviews)
5 Bedrooms
3 Baths
10 Guests
2600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $354/Night
7 Nights - US $2,479
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
2561.81 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $624/Night
7 Nights - US $4,368
Condo
10.0(54 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $372/Night
7 Nights - US $2,603
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
7 Guests
1819.1 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $270/Night
7 Nights - US $1,890
Condo
10.0(51 Reviews)
3 Bedrooms
2 Baths
10 Guests
1900 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $361/Night
7 Nights - US $2,528
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $120/Night
7 Nights - US $840
New
House
10.0(47 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $951/Night
7 Nights - US $6,657
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:
- Original Beach Styled Cottage
- Beachfront Condo, 1st Floor Ocean View
- Cozy cottage on the Miller farm.
- Beachfront, Oceanfront, Rehoboth, DE on the Boardwalk
- LUXURY CONDO. CLOSE TO BEACH!
- GORGEOUS & BEST IN TOWN! - Walk to the Beach and Shops! Beautifully Remodeled!
- Stay Play Dewey - Oceanfront Dewey Beach Townhouse
- Beach Block Townhouse With NEW Everything & Ocean Views ☀️🦀🐬
- Waterfront Beach House! Secluded Retreat on the Bay.
- Bethany Bay Relaxation Awaits
2. How many Winter Rentals are available in Delaware?
Currently, the total number of properties listed by RBO in 2026 is over 7499 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
US $806/Night
7 Nights - US $5,642
New
House
10.0(41 Reviews)
5 Bedrooms
3 Baths
13 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $781/Night
7 Nights - US $5,466
House
10.0(40 Reviews)
5 Bedrooms
3 Baths
12 Guests
1950 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $895/Night
7 Nights - US $6,268
Condo
10.0(40 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $511/Night
7 Nights - US $3,579
New
House
10.0(40 Reviews)
3 Bedrooms
2 Baths
7 Guests
1850 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $489/Night
7 Nights - US $3,424
House
10.0(34 Reviews)
6 Bedrooms
3 Baths
11 Guests
1980 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $359/Night
7 Nights - US $2,515
New
House
10.0(31 Reviews)
3 Bedrooms
3 Baths
14 Guests
1750 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $339/Night
7 Nights - US $2,375
New
House
10.0(29 Reviews)
4 Bedrooms
3 Baths
10 Guests
2200 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
US $983/Night
7 Nights - US $6,884
House
10.0(23 Reviews)
4 Bedrooms
3 Baths
8 Guests
2200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $401/Night
7 Nights - US $2,805
New
House
10.0(21 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $394/Night
7 Nights - US $2,759
House
10.0(16 Reviews)
4 Bedrooms
2 Baths
6 Guests
2344 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
US $325/Night
7 Nights - US $2,272
New
House
10.0(13 Reviews)
6 Bedrooms
3 Baths
14 Guests
2800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $985/Night
7 Nights - US $6,897
