Search Holiday Rentals in Head of the Harbor

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Check prices for these dates

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

Our top choices for Head of the Harbor holiday rentals

Deluxe Apartment, Non Smoking, Private Bathroom | Interior

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
The price is ฿4,779
฿8,432 total
includes taxes & fees
3 May - 4 May
Sundown Escape-South Shore Long Island
Comfort Room | Living area

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is ฿5,520
฿9,525 total
includes taxes & fees
4 May - 5 May
Spacious 3BR Family Home Near Everything
Classic Suite | 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 ฿5,731
฿8,574 total
includes taxes & fees
26 May - 27 May
DUNE Fairfield Beach
Apartment (4 Bedrooms) | 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 ฿5,234
฿18,362 total
includes taxes & fees
29 May - 30 May
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
House (3 Bedrooms) | 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 ฿10,664
฿20,021 total
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

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2/10 Terrible
"This hotel was a nightmare.. check in Sonia was not polite at all attitude and tried to tell me that we couldn’t do two card split payments she had an attitude check in took over 20 minutes she kept looking over to the front desk supervisor for help but she was to busy playing with a cat was also very rude for a supervisor our first room had mold in it the shower pole was hanging off the wall and water was coming out of the shower the man at the front desk was also very rude the only friendly faces in that entire hotel were Melinda and Juan they would be better running that place it’s a joke drive further out and go to the location in center reach. "
Maria 3-night trip
Posted 4 hours ago
Holiday Inn Express Hauppauge-Long Island

Find out more about Head of the Harbor

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

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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 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.