Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Head of the Harbor vacation rentals

Interior

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
The price is P8,927
P15,750 total
includes taxes & fees
May 24 - May 25
Sundown Escape-South Shore Long Island
Living area

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is P11,150
P18,807 total
includes taxes & fees
May 4 - May 5
Spacious 3BR Family Home Near Everything
Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (84 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is P10,803
P16,162 total
includes taxes & fees
May 26 - May 27
DUNE Fairfield Beach
Interior

Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is P9,717
P34,230 total
includes taxes & fees
May 29 - May 30
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Interior

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Rocky Point
The price is P19,919
P37,399 total
includes taxes & fees
May 24 - May 25
Charming Rocky Point Home ~ 1 Mi to Beach!
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

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ Loved The Inn at Fox Hollow! Super clean, great location for Hofstra, and the staff was unbelievably friendly (and thankfully had a great sense of humor when I confidently said “Of course I have my phone”… while it was still sitting at breakfast 😅). Breakfast was excellent, and the dinner amenity was such a nice bonus too. We loved it so much we’re already planning to stay again for move-in week—and we want to bring our parents too… so please feel free to hook us up 😉 Also, side note: I really wish hotels offered teacher discounts… because traveling during school breaks costs twice as much, and teachers definitely aren’t out here living the luxury life! 😭"
Timothy 1-night trip
Posted 2 hours ago
The Inn At Fox Hollow Hotel

Find out more about Head of the Harbor

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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 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 Harmony Vineyards and Stony Brook Grist Mill.

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.