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Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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 P13,210
P21,158 total
includes taxes & fees
Aug 2 - Aug 3
Spacious 3BR Family Home Near Everything
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, (103 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is P10,980
P16,364 total
includes taxes & fees
Aug 24 - Aug 25
DUNE Fairfield Beach
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 P8,105
P18,359 total
includes taxes & fees
Aug 6 - Aug 7
Sundown Escape-South Shore Long Island
Interior

4. 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 P10,108
P32,955 total
includes taxes & fees
Aug 3 - Aug 4
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
4 bedrooms, high-speed internet

5. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is P44,579
P67,329 total
includes taxes & fees
Aug 19 - Aug 20
Stareway to Heaven in Fairfield
Interior

6. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
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

Danfords Hotel and Marina

Danfords Hotel and Marina

8/10 Good
"Nice area, needs updating."
lea 3-night trip
Posted 1 hour ago
Danfords Hotel and Marina

Find out more about Head of the Harbor

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Look no further and take a look at our great range of rental properties in Head of the Harbor!

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 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.