- Barbados
- St. Philip
- Ocean City
- Winter Rental
Ocean City Winter Rentals & Holiday Homes
Discover winter rentals Ocean City - We found 10 exact matches
When do you want to travel?
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
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- Pool
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- Pool
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- Pet Friendly
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- View
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- Designated Smoking Area
- Air Conditioner
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- Child Friendly
- Air Conditioner
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- Private Pool
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- View
- Ocean View
- Air Conditioner
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- View
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Child Friendly
- Parking
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- View
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
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- Pet Friendly
- Pool
- Pool
- TV
- Private Pool
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- TV
- Balcony/Terrace
- Bedding/Linens
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Child Friendly
Frequently Asked Questions About Ocean City Winter Rental
What are the top rated Winter Rentals in Ocean City?
There are a lot of options in Ocean City. If you plan on staying in the Ocean City area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Ocean City:
- Villanor Cottage - a delightful cottage with great sea views
- Crow's Nest, Cliff Front, Ocean Views
- Pool Side Cottage in Barbados
- Cliffside house with stunning sea view w/private pool 10 min walk to the beach!
- Cliff top Luxury 2 bedroom Apartment
- Luxury cliff apartment with fantastic pool and great sea views.
- Come stay in an authentic Bajan Chattel Home in lovely St. Phillip
- Sunrise Breeze Barbados
- Cliff Edge Villa - St. Philip
- Belleview Cozy Cottage
How much does it cost to rent a place to stay near Ocean City in the wintertime?
The average cost for winter rentals in Ocean City is $355 per night. Beachbaycottages has a wide list of great winter places to stay near Ocean City that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Ocean City that allow pets?
Yes, here are the top cottage/chalet rentals in Ocean City that allow you to bring your pet or dog:
- ABBE DYNASTY: Ocean View Holiday Home
- ABBE Garden Hideaway
- Luxury cliff apartment with pool and sea views.
- Luxury Villa With Pool, Outdoor Beds on Cliff Top Near Crane Beach
- Pool Side Cottage in Barbados
- Sunrise Breeze Barbados
- Relax in the Ocean Acacia townhouse
- Belleview Cozy Cottage
See all pet-friendly vacation rentals in Ocean City on Beachbaycottages
Do you have any winter rentals in Ocean City that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Ocean City to find what works for you.
Are there winter accommodations in Ocean City that have indoor swimming pools?
As of 2026, the data from Beachbaycottages shows that there are over 10 private swimming pools or indoor pools accommodations near Ocean City along with other great amenities.