Discover winter rentals Headland - We found 35 exact matches
About Headland Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Headland perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Headland. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Headland and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Headland Winter Rentals
What are the top rated Winter Rentals in Headland?
There are a lot of options in Headland. If you plan on staying in the Headland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Headland:
- Quiet and Cozy Home Away From Home.
- Stacey's HideawaynCozy, comfy beach home-30 minutes from MBJ Airport
- Wabi-Sabi Villa
- Veronica Villa 68
- Kelso Sunset Villas - Full Property with 2 VillasnLucea, Hanover
- Free Airport Shuttle | Luxe Lucea Home | Pool
- Serene Oceanview Home in Oceanpointe, Lucea, Hanover, Jamaica
- VillaMerissa, Lucea @ Oceanpointe! Beach, Pool, Tennis, Gym, near Airport
- Hilltop Studio with ocean views, free daily breakfast and airport pickup.
- Apartment - Walk to the Beach
How much does it cost to rent a place to stay near Headland in the wintertime?
The average cost for winter rentals in Headland is $359 per night. Vacation Cottage has a wide list of great winter places to stay near Headland that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Headland that allow pets?
Yes, here are the top cottage/chalet rentals in Headland that allow you to bring your pet or dog:
- Quiet and Cozy Home Away From Home.
- Veronica Villa 68
- Wabi-Sabi Villa
- Stacey's HideawaynCozy, comfy beach home-30 minutes from MBJ Airport
See all pet-friendly vacation rentals in Headland on Vacation Cottage
Do you have any winter rentals in Headland that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Headland to find what works for you.
Are there winter accommodations in Headland that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 35 private swimming pools or indoor pools accommodations near Headland along with other great amenities.
Do any winter holiday rentals in Headland have hot tubs?
About 35 holiday rentals in Headland boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Headland?
Yes, there are many luxury places to stay in Headland for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Headland with all the best amenities for your next trip.
