Head of the Harbor Holiday Rentals

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Holiday Rentals in Head of the Harbor

Apartment in Fairfield

3.0 star property
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

Holiday Home in Fairfield

10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is AU$819
includes taxes & fees
9 Dec - 10 Dec
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Cottage in Miller Place

10.0 out of 10, Exceptional, (15)
"Lovely cottage with great host! All was wonderful!! very happy with our 17 day vacation!"
United States
Laurita S.
The price is AU$502
includes taxes & fees
4 Dec - 5 Dec
Cozy Country Cottage #4

Apartment in West End - West Side

10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is AU$430
includes taxes & fees
8 Dec - 9 Dec
Renovated 2BR Retreat / Modern Comforts Included

Apartment in Mastic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is AU$296
includes taxes & fees
3 Dec - 4 Dec
South Shore Studio in Mastic

Apartment in Fairfield

10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is AU$487
includes taxes & fees
8 Dec - 9 Dec
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Apartment in Downtown Bridgeport

10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveller
The price is AU$253
includes taxes & fees
7 Dec - 8 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Cottage in Miller Place

9.0 out of 10, Wonderful, (15)
"Cottage was awesome!! It was clean and welcoming. We felt at home. Great place to stay."
United States
Bridget
The price is AU$524
includes taxes & fees
5 Dec - 6 Dec
Cozy Country Cottage #2

Holiday Home in Ronkonkoma

2.0 star property
10.0 out of 10, Exceptional, (4)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$460
includes taxes & fees
3 Dec - 4 Dec
The Royal Suite - Ronkonkoma

Holiday Home in Shirley

10.0 out of 10, Exceptional, (21)
"The place was very well sized and in a lovely location by the beach. Eddie was extremely responsive to all of our questions through out our stay. Would highly recommend!"
United States
Matt H.
The price is AU$957
includes taxes & fees
3 Dec - 4 Dec
3 Story Beach Waterview, 3 KING bed, golf putting green!

Holiday Home in Bayport

2.0 star property
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is AU$431
includes taxes & fees
3 Dec - 4 Dec
Peaceful private 2-bedroom house in Bayport.Amazing location!

Apartment in Central Islip

2.0 star property
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$391
includes taxes & fees
6 Dec - 7 Dec
Cozy 2 bedroom retreat in long island

Apartment in Coram

10.0 out of 10, Exceptional, (3)
"Would definitely stay again "
United States
Katherine R.
The price is AU$308
includes taxes & fees
1 Jan - 2 Jan 2026
JC Entire Apartment remodeled, close to Airport and Ferry

Apartment in Centereach

7.8 out of 10, Good, (10)
"I answered this. Safe and Quit."
United States
John
The price is AU$577
includes taxes & fees
6 Dec - 7 Dec
Spacious one Bedroom Apt with private entrance

Apartment in Westport

8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is AU$428
includes taxes & fees
4 Dec - 5 Dec
Sweet Studio w/ Lounge & Pool Table

Apartment in Coram

9.4 out of 10, Exceptional, (6)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is AU$409
includes taxes & fees
3 Dec - 4 Dec
Cozy king suite with kitchen and dining area.

Apartment in Kings Park

2.0 star property
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$276
includes taxes & fees
5 Dec - 6 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Holiday Home in Stony Brook

2.0 star property
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is AU$803
includes taxes & fees
5 Dec - 6 Dec
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Holiday Home in Fairfield

10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is AU$772
includes taxes & fees
18 Dec - 19 Dec
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Holiday Home in Stony Brook

2.0 star property
8.0 out of 10, Very good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is AU$344
includes taxes & fees
3 Dec - 4 Dec
Newly renovated Private bedroom near Stony Brook University
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.