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Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Head of the Harbor holiday 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 RM774
RM1,284 total
includes taxes & fees
25 Aug - 26 Aug
Spacious 3BR Family Home Near Everything
Iron/ironing board, free WiFi, 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 RM712
RM1,065 total
includes taxes & fees
13 Sept - 14 Sept
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 RM534
RM1,210 total
includes taxes & fees
11 Sept - 12 Sept
Sundown Escape-South Shore Long Island
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 RM1,842
RM3,027 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 10 hours ago
Hyatt Regency Long Island

Find out more about Head of the Harbor

Search for holiday rentals in Head of the Harbor on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Head of the Harbor using one of the methods below:

  • View our selection of featured holiday rentals in 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 holiday rentals in Head of the Harbor?

Yes, there are holiday rentals close to the most popular sights in Head of the Harbor, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals like in Head of the Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Head of the Harbor. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.