Discover winter rentals Head of the Harbor - We found 37 exact matches
About Head of the Harbor Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Head of the Harbor, NY 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 Head of the Harbor. 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 Head of the Harbor and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Head of the Harbor Winter Rentals
What are the top rated Winter Rentals in Head of the Harbor?
There are a lot of options in Head of the Harbor. If you plan on staying in the Head of the Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Head of the Harbor:
- Snow Birds, Transitions, Temporary Work Assignments, This is it!
- Tranquil & Pet-Friendly Estate on Long Island!
- Charming 1 bedroom Stony Brook cottage -walking distance to village & university
- Blue Cottage East Setauket
- Historic Beautifully Preserved 1800’s Retreat - Large 1bd Apt in PJ Village
- The Bella Vista St James! Waterfront house with a beach dock and so much more!
- The Suite at North Shore Long Island, Prime Location, Unique and sophisticated
- Private 1 bedroom apt in a quiet neighborhood, close to all!
- 'Dreams of Paradise' Luxury Home w/Pool!
- Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer
How much does it cost to rent a place to stay near Head of the Harbor in the wintertime?
The average cost for winter rentals in Head of the Harbor is $1,148 per night. Vacation Cottage has a wide list of great winter places to stay near Head of the Harbor that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Head of the Harbor that allow pets?
Yes, here are the top cottage/chalet rentals in Head of the Harbor that allow you to bring your pet or dog:
- Beautiful Private Room Near Stony Brook University
- Dreams of Paradise Luxury Home with Pool!
- 'dreams of Paradise' Luxury Home w/Pool!
- Snow Birds, Transitions, Temporary Work Assignments, This is it!
See all pet-friendly vacation rentals in Head of the Harbor on Vacation Cottage
Do you have any winter rentals in Head of the Harbor that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Head of the Harbor to find what works for you.
Are there winter accommodations in Head of the Harbor that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 37 private swimming pools or indoor pools accommodations near Head of the Harbor along with other great amenities.
Do any winter holiday rentals in Head of the Harbor have hot tubs?
About 37 holiday rentals in Head of the Harbor boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Head of the Harbor?
Yes, there are many luxury places to stay in Head of the Harbor for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Head of the Harbor with all the best amenities for your next trip.
