89+ Hotel & Resort Deals in Head of the Harbor |
  1. USA
  2. New York
  3. Head of the Harbor

Head of the Harbor Hotels, Resorts, and Rentals

About Head of the Harbor Vacation Rentals

There are more than 89 places to stay in Head of the Harbor that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Head of the Harbor.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Head of the Harbor, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Head of the Harbor. Places to stay near Head of the Harbor are 625.86 ft² on average, with prices averaging US $650 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Head of the Harbor with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

Show more
Show less

Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Head of the Harbor

Type Count
Vacation Homes 44
Holiday Apartments 23
Cottages 3
Villas 2
B&B 1
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Head of the Harbor

★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Head of the Harbor.

Weather in Head of the Harbor, NY

View the weather forecast for Head of the Harbor before booking your Head of the Harbor Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Head of the Harbor's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Head of the Harbor's top attractions, neighborhoods, and points of interest.


Avalon Park and Preserve
Harmony Vineyards
Stony Brook Grist Mill
Stony Brook University
Port Jefferson
Paramount Theater
Fairfield University
Lake Ronkonkoma
Norwalk Maritime Aquarium
Baseball Heaven
Oheka Castle
Tanger Outlets
Farmingdale State College
Webster Bank Arena
Sunken Meadow State Park
Historic South Norwalk
Robert Moses Beach
Adventureland
Ocean Beach
Sagamore Hill National Historic Site

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


St. James 76 Properties
Avalon Park and Preserve 74 Properties
Stony Brook Grist Mill 74 Properties
Harmony Vineyards 73 Properties

Frequently Asked Questions About Head of the Harbor?

What are the top hotels or resorts in Head of the Harbor?

You have a lot of choices in or near Head of the Harbor. If you need a hotel in the Head of the Harbor area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Head of the Harbor:

How many vacation rentals have private pools in Head of the Harbor?

There are 3 accommodation options with private pools in or near Head of the Harbor. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

How many hotels, resorts, or rentals are available in Head of the Harbor?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 89 in the Head of the Harbor area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Head of the Harbor.


People Also Ask

There are 15 hotels in Head of the Harbor and 70 rentals

Recently Booked Hotels, Resorts, or Rentals in Head of the Harbor