Condo
10.0(251 Reviews)
1 Bedroom
2 Guests
Oceanfront
Parking
Pool
Ocean View
US $202/Night
7 Nights - US $1,413
Delaware Winter Rentals & Holiday Homes
Discover winter rentals Delaware - We found 7682 exact matches
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Compare Winter Rental in Delaware
10.0
Bed & Breakfast
10.0(20 Reviews)
1 Bedroom
2 Guests
- Oceanfront
Breakfast- Parking
- Ocean View
US $244/Night
7 Nights - US $1,707
Bed & Breakfast
10.0(133 Reviews)
1 Bedroom
- Breakfast
- Parking
Balcony/Terrace
Kitchen
US $219/Night
7 Nights - US $1,536
House
10.0(188 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $400/Night
7 Nights - US $2,801
Apartment
10.0(10 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $243/Night
7 Nights - US $1,701
Condo
10.0(180 Reviews)
2 Bedrooms
6 Guests
Hot Tub- Parking
- Pool
- Ocean View
US $187/Night
7 Nights - US $1,311
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
EV Charge Station- Parking
- Ocean View
US $382/Night
7 Nights - US $2,674
Condo
10.0(159 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Pool
Spa
US $208/Night
7 Nights - US $1,455
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Spa
View
US $704/Night
7 Nights - US $4,928
Apartment
10.0(144 Reviews)
1 Bedroom
3 Guests
Private Pool- Oceanfront
- Parking
- Pool
US $214/Night
7 Nights - US $1,497
US $200/Night
7 Nights - US $1,400
Condo
10.0(143 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $191/Night
7 Nights - US $1,337
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
Internet
US $695/Night
7 Nights - US $4,865
House
10.0(130 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $259/Night
7 Nights - US $1,813
Cottage
10.0(109 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $335/Night
7 Nights - US $2,344
Cottage
10.0(108 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $418/Night
7 Nights - US $2,925
Condo
10.0(106 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $260/Night
7 Nights - US $1,820
House
10.0(91 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $316/Night
7 Nights - US $2,211
Apartment
10.0(90 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $427/Night
7 Nights - US $2,987
Condo
10.0(86 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $487/Night
7 Nights - US $3,407
House
10.0(83 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $367/Night
7 Nights - US $2,572
Condo
10.0(82 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $270/Night
7 Nights - US $1,887
Condo
10.0(80 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $354/Night
7 Nights - US $2,477
Condo
10.0(79 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $277/Night
7 Nights - US $1,940
About Delaware Winter Rental on BedroomVillas
At BedroomVillas, we feature a wide range of listings for accommodations in Delaware, DE that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Delaware, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Delaware and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Delaware Winter Rentals
What are the top rated 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, Renovated inside.
- 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 4BR Townhouse, 2 Primary Bedrooms, east of route 1, POOL, close to beach
- Luxury Condo - Family-Friendly - Prime location
- New Beautifully Appointed Home Perfect for Large Groups - Dogs Considered
- Availability for Sea Witch Festival 26' Weekend! Community near Dart bus shuttle
How much does it cost to rent a place to stay near Delaware in the wintertime?
The average cost for winter rentals in Delaware is $538 per night. BedroomVillas has a wide list of great winter places to stay near Delaware that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Delaware that allow pets?
Yes, here are the top cottage/chalet rentals in Delaware that allow you to bring your pet or dog:
- Beachfront, Oceanfront, Rehoboth, DE on the Boardwalk
- Miller-Dunham House B&B
- The Towers Bed & Breakfast
- Waterfront Beach House! Secluded Retreat on the Bay.
See all pet-friendly vacation rentals in Delaware on BedroomVillas
Do you have any winter rentals in Delaware that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Delaware to find what works for you.
Are there winter accommodations in Delaware that have indoor swimming pools?
As of 2026, the data from BedroomVillas shows that there are over 7682 private swimming pools or indoor pools accommodations near Delaware along with other great amenities.
Do any winter holiday rentals in Delaware have hot tubs?
About 7682 holiday rentals in Delaware boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Delaware?
Yes, there are many luxury places to stay in Delaware for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Delaware with all the best amenities for your next trip.
