Head of the Harbor Holiday Rentals

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Holiday Rentals in Head of the Harbor

The Bella Vista St James! Waterfront house with a beach dock and so much more!

Saint James
10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
The Bella Vista St James! Waterfront house with a beach dock and so much more!

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$227
includes taxes & fees
1 Jan - 2 Jan 2026
Business or Weekend escape

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (13)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is AU$275
includes taxes & fees
4 Dec - 5 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is AU$752
includes taxes & fees
8 Dec - 9 Dec
Captain's Cottage - Cold Spring Harbor Water Views

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is AU$960
includes taxes & fees
4 Dec - 5 Dec
Modern Vacation home. Close to The Hamptons

Cozy Country Cottage #3

Miller Place
10.0 out of 10, Exceptional, (29)
"Fantastic stay! "
United States
Michael V.
The price is AU$502
includes taxes & fees
16 Dec - 17 Dec
Cozy Country Cottage #3

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

Ocean Beach
9.0 out of 10, Wonderful, (53)
"The location is superb, can’t do much better! Towards the end of the main strip for privacy but still right near the action that you come to Ocean Beach for. The rental was clean and stocked with essentials upon our arrival (definitely a life-saver) with the onsite washer/dryer a bonus!As for the property owner, I’m happy to report that this one is a pleasure… congenial, accommodating and professional from the start of the reservation process and onward.We are looking forward to returning next...
United States
Amy B.
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Coram
9.4 out of 10, Exceptional, (6)
"Great first time doing Vrbo great experience would do again "
United States
Rodrigo M.
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Charming Home in Seaside

2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"Amazing beautiful property in a rustic urban environment. Perfect check in, super comfortable, TVs in every room… essentially a new house. Close to the water and amphitheater. If you’re used to city life we’d recommend it, because we are!"
United States
Matt H.
Charming Home in Seaside

LUXURY BAY SHORE HOME

2.0 star property
Bay Shore
2.0 out of 10, (2)
"DO NOT book this house! I booked this house for Thanksgiving day visiting family. I received confirmation and everything. However till the day of arrival I never received any instruction on checking in. I called multiple times and only got voice mail in spanish. Finally I received a message saying this house was no longer available several hours before checking in! We had to scramble to find hotel rooms for 10 people. It was totally unacceptable!"
United States
Yan
LUXURY BAY SHORE HOME

Walk to Beach 2BR Near Dining & Shopping

Rocky Point
6.6 out of 10, (25)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is AU$360
includes taxes & fees
4 Dec - 5 Dec
Walk to Beach 2BR Near Dining & Shopping

Cozy 2 bedroom retreat in long island

2.0 star property
Central Islip
8.0 out of 10, Very good, (2)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is AU$378
includes taxes & fees
16 Dec - 17 Dec
Cozy 2 bedroom retreat in long island

4-bedroom house in awesome Brookhaven with AC

Brookhaven
4-bedroom house in awesome Brookhaven with AC

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Ocean Bay Park
9.0 out of 10, Wonderful, (32)
"Cute space - great communication - would come back again! "
United States
Cathy N.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Modern Apartment in Black Rock

2.0 star property
Black Rock Historic District
9.6 out of 10, Exceptional, (12)
"Visited with family for the weekend and the property manager was great with communication and the location was fantastic."
United States
Caroline C.
Modern Apartment in Black Rock

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport
9.4 out of 10, Exceptional, (13)
"All went well. Owners live in cottage on property. The bay is gorgeous."
United States
Rob M.
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer

Ronkonkoma
9.0 out of 10, Wonderful, (6)
"Enjoyed our stay, property was as advertised. Quiet, comfortable neighborhood, and host was prompt with all communications."
United States
Brian O.
Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite
9.8 out of 10, Exceptional, (71)
"Cute cottage in great location. We stay here every time we are in town and are never disappointed. "
United States
Rosanne A.
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Home Away from Home – 3BR Retreat with Amenities

Hauppauge
10.0 out of 10, Exceptional, (8)
Home Away from Home – 3BR Retreat with Amenities
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

Find out more about Head of the Harbor

Everything you need to know about Head of the Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Head of the Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Head of the Harbor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Head of the Harbor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Head of the Harbor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Head of the Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Head of the Harbor holiday rentals we have selected for you start as low as AU$227 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Head of the Harbor rentals

At Expedia, we put the best Head of the Harbor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Head of the Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Head of the Harbor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Head of the Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 are some of the best holiday rentals that Head of the Harbor has to offer?

Business or Weekend escape: This holiday home rental outside of Head of the Harbor offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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.