Apartment
9.8(49 Reviews)
1 Bedroom
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $111/Night
7 Nights - US $779
Bear Winter Rentals & Holiday Homes
Discover winter rentals Bear - We found 33 exact matches
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Compare Winter Rental in Bear
9.8
House
10.0(1 Review)
4 Bedrooms
8 Guests
Oceanfront- Parking
Pool
Ocean View
US $309/Night
7 Nights - US $2,160
Hotel
8.2(1000 Reviews)
Breakfast- Parking
- Kitchen
- Air Conditioner
US $111/Night
7 Nights - US $779
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $296/Night
7 Nights - US $2,069
Villa
10.0(1 Review)
1 Bedroom
6 Guests
- Parking
View- Air Conditioner
Internet
US $315/Night
7 Nights - US $2,205
Condo
2 Bedrooms
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $120/Night
7 Nights - US $841
House
9.0(173 Reviews)
10 Bedrooms
23 Guests
- Parking
Spa- Balcony/Terrace
- View
US $179/Night
7 Nights - US $1,250
Apartment
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $448/Night
7 Nights - US $3,134
Hotel
8.3(262 Reviews)
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $97/Night
7 Nights - US $679
Apartment
10.0(6 Reviews)
5 Bedrooms
12 Guests
Private Pool
Hot Tub- Parking
- Pool
US $968/Night
7 Nights - US $6,776
Hotel
7.8(72 Reviews)
- Oceanfront
- Parking
- Pool
- Ocean View
US $162/Night
7 Nights - US $1,135
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $2,896/Night
7 Nights - US $20,272
Hotel
7.7(97 Reviews)
- Breakfast
EV Charge Station- Parking
- Air Conditioner
US $134/Night
7 Nights - US $941
US $723/Night
7 Nights - US $5,063
US $680/Night
7 Nights - US $4,757
House
10.0(1 Review)
3 Bedrooms
4 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $368/Night
7 Nights - US $2,575
House
10.0(1 Review)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $209/Night
7 Nights - US $1,463
House
9.6(25 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $332/Night
7 Nights - US $2,325
Apartment
9.6(5 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $254/Night
7 Nights - US $1,778
House
8.0(20 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $375/Night
7 Nights - US $2,624
House
8.0(3 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $628/Night
7 Nights - US $4,397
House
4 Bedrooms
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $304/Night
7 Nights - US $2,131
House
4 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $261/Night
7 Nights - US $1,829
Apartment
6.8(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $157/Night
7 Nights - US $1,096
About Bear Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 33 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Bear Winter Rentals
What are the top rated Winter Rentals in Bear?
There are a lot of options in Bear. If you plan on staying in the Bear area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Bear:
- Homewood Suites by Hilton Newark-Wilmington South Area
- Sonesta ES Suites Wilmington - Newark
- Best Western Plus Newark/Christiana Inn
- Welcome To Morgan Manor
- Hidden Gem, 8 person condo in Newark with WiFi, AC, hot tub, near UD.
- Majestic Room to Stay w/ Excellent Room Service!
- Your serene home
- 2 Connecting Suites at a Hotel
- 2 Connecting Suites at a Hotel
How much does it cost to rent a place to stay near Bear in the wintertime?
The average cost for winter rentals in Bear is $408 per night. Casai has a wide list of great winter places to stay near Bear that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Bear that allow pets?
Yes, here are the top cottage/chalet rentals in Bear that allow you to bring your pet or dog:
- Country Get Away Studio Apartment
- Exec 4BR3BA 3 Desks, Fios Garage Adults 18
- Four Points by Sheraton Newark Christiana Wilmington
- Fantastic 2-bedroom condo with AC in vibrant Newark. WiFi with 65 inch smart TV
See all pet-friendly vacation rentals in Bear on Casai.com
Do you have any winter rentals in Bear that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Bear to find what works for you.
Are there winter accommodations in Bear that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 33 private swimming pools or indoor pools accommodations near Bear along with other great amenities.
Do any winter holiday rentals in Bear have hot tubs?
About 33 holiday rentals in Bear boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Bear?
Yes, there are many luxury places to stay in Bear for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Bear with all the best amenities for your next trip.
