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Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Head of the Harbor vacation rentals

Terrace/patio

1. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AED 704
AED 1,168 total
includes taxes & fees
25 Aug - 26 Aug
Spacious 3BR Family Home Near Everything
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (110 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is AED 647
AED 969 total
includes taxes & fees
13 Sep - 14 Sep
DUNE Fairfield Beach
Deluxe Apartment, Non Smoking, Private Bathroom | Interior

3. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is AED 457
AED 1,067 total
includes taxes & fees
11 Sep - 12 Sep
Sundown Escape-South Shore Long Island
House (4 Bedrooms) | Interior

4. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is AED 1,675
AED 2,753 total
includes taxes & fees
30 Aug - 31 Aug
4 Mi to Beach & Dtwn! Charming Fairfield Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Head of the Harbor Hotel Reviews

Hyatt Regency Long Island

Hyatt Regency Long Island

10/10 Excellent
"Overall a great place. Minimal noise even w 6 wedding parties in our experience. Breakfast was great and I am very picky."
Irina 2-night trip
Posted 4 hours ago
Hyatt Regency Long Island

Frequently asked questions

Are there vacation rentals in Head of the Harbor?

Yes, we offer vacation rentals close to top attractions in Head of the Harbor, or you can choose a more remote option if you'd like a relaxing place to stay. Head of the Harbor is known for its wineries and parks.

What are some of the best vacation rentals that Head of the Harbor has to offer?

Charming Home in Seaside: This vacation home rental near Head of the Harbor is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Head of the Harbor?

Explore the area and family-friendly sights such as Vanderbilt Museum, or get out into nature at a spot like Avalon Park and Preserve. Other places in town to visit include Stony Brook Grist Mill and Harmony Vineyards.

What are vacation rentals like in Head of the Harbor?

Vacation rentals are private accommodations you can reserve for several days or longer in Head of the Harbor. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family gatherings.