Head of the Harbor Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Head of the Harbor holiday rentals

Living area

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is S$331
includes taxes & fees
25 May - 26 May
Spacious 3BR Family Home Near Everything
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 S$701
includes taxes & fees
29 May - 30 May
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
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, (88 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is S$338
includes taxes & fees
26 May - 27 May
DUNE Fairfield Beach
Exterior

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 S$400
includes taxes & fees
25 May - 26 May
Sundown Escape-South Shore Long Island
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 S$787
includes taxes & fees
24 May - 25 May
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

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

2/10 Terrible
"Too crowded"
Thomas 1-night trip
Posted 11 hours ago
Jake's 58 Casino Hotel - Adult Only

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 Harmony Vineyards and Stony Brook Grist Mill.

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.