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 price is NZ$3,651
includes taxes & fees
16 Nov - 17 Nov
The Bella Vista St James! Waterfront house with a beach dock and so much more!

Tiny Home Private, Students, Nurses, Tech

Bay Shore
8.4 out of 10, Very good, (6)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
United States
Melanie M.
The price is NZ$378
includes taxes & fees
20 Nov - 21 Nov
Tiny Home Private, Students, Nurses, Tech

Nature Meets Village - Walkable Northport

Northport
The price is NZ$1,095
includes taxes & fees
23 Nov - 24 Nov
Nature Meets Village - Walkable Northport

The Royal Suite - Ronkonkoma

2.0 star property
Ronkonkoma
10.0 out of 10, Exceptional, (4)
"The host was highly responsive and friendly. The stay was exactly what I needed for a few nights. The room was cozy, clean, and the bed was heavenly. The shower was perfect!!! I would stay again. "
United States
Tara B.
The price is NZ$518
includes taxes & fees
13 Nov - 14 Nov
The Royal Suite - Ronkonkoma

Cozy Country Cottage #4

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 NZ$572
includes taxes & fees
6 Dec - 7 Dec
Cozy Country Cottage #4

Renovated 2BR Retreat / Modern Comforts Included

West End - West Side
10.0 out of 10, Exceptional, (2)
"My stay was comfortable for an over night stay after family celebration. I would definitely use this unit again if I travel without a senior person. My suggestion is to clearly identify the unit regarding the stair climbing for prospective renters for the second and third floor. Thank you,"
United States
Magalie L.
The price is NZ$510
includes taxes & fees
1 Dec - 2 Dec
Renovated 2BR Retreat / Modern Comforts Included

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

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (11)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is NZ$316
includes taxes & fees
18 Nov - 19 Nov
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

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 NZ$557
includes taxes & fees
9 Dec - 10 Dec
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (75)
"Great stay"
Canada
Gilles
DUNE Fairfield Beach

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Downtown Bridgeport
9.0 out of 10, Wonderful, (6)
"My daughter and I stayed here for two nights. We drove from Philadelphia, PA to see a Conan Gray concert on Friday night. The apartment was absolutely beautiful! There were two huge water bottles in the refrigerator, snacks to hold us over until we could get our own food, and all kinds of small amenities (toothbrushes, toothpaste, ear plugs, q-tips, shampoo, conditioner, etc). The apartment was spotless and beautiful, and the bed was the most comfortable bed my daughter and I have ever slept on....
United States
Lisa
The price is NZ$407
includes taxes & fees
24 Nov - 25 Nov
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Spacious one Bedroom Apt with private entrance

Centereach
8.4 out of 10, Very good, (9)
"My husband, two boys (6 & 11) and I stayed in this quaint, little, clean apartment for four nights. They provided coffee, creamer and bathroom necessities. It was perfect for a short stay. When we did need something the owner was quick to reply and get it to us. If need be we will stay here again."
United States
NATALIE P.
The price is NZ$662
includes taxes & fees
25 Nov - 26 Nov
Spacious one Bedroom Apt with private entrance

3 Story Beach Waterview, 3 KING bed, golf putting green!

Shirley
10.0 out of 10, Exceptional, (21)
"Eddie was a great host, we loved the area and will definitely keep him in mind when we plan on returning."
United States
Faraz S.
The price is NZ$1,085
includes taxes & fees
16 Nov - 17 Nov
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy Country Cottage #2

Miller Place
9.0 out of 10, Wonderful, (14)
"We were looking for a property close to my in-laws where we could bring our 2 pups and we found this wonderful home. The cottage is much bigger than expected and beautifully furnished and well-equipped. Full size washer and dryer with newer appliances and a fenced in yard for the dogs. AC also worked very nicely during a very warm week. Plenty of towels, sheets, and roll away bed made our stay perfect. Definitely would stay again!"
United States
Robin M.
The price is NZ$598
includes taxes & fees
20 Nov - 21 Nov
Cozy Country Cottage #2

Cozy 2 bedroom retreat in long island

2.0 star property
Central Islip
8.0 out of 10, Very good, (1)
"Some noise at night. Great shower and great water pressure but shower head suction cup does not stay on wall."
United States
Suzanne S.
The price is NZ$436
includes taxes & fees
13 Nov - 14 Nov
Cozy 2 bedroom retreat in long island

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Very nice stay and very clean"
United States
Markel W.
The price is NZ$249
includes taxes & fees
18 Nov - 19 Nov
Business or Weekend escape

Your Perfect Getaway Between Farmingdale & Amityville

Amityville
10.0 out of 10, Exceptional, (2)
"The whole experience was great"
United States
David
The price is NZ$382
includes taxes & fees
14 Nov - 15 Nov
Your Perfect Getaway Between Farmingdale & Amityville

Private 1 bedroom apt in a quiet neighborhood, close to all!

Centereach
9.6 out of 10, Exceptional, (26)
"Property is close to Stony Brook University and was very comfortable and clean. Would definitely stay here again."
United States
Erik
The price is NZ$452
includes taxes & fees
15 Nov - 16 Nov
Private 1 bedroom apt in a quiet neighborhood, close to all!

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Brentwood
9.6 out of 10, Exceptional, (33)
"Jennifer was a nice host, very communicative. We felt very at home and safe. There was no noise and it was peaceful, I would definitely book here again, thanks Jeniffier!!!"
United States
Cindy E.
The price is NZ$291
includes taxes & fees
13 Nov - 14 Nov
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

West End - West Side
10.0 out of 10, Exceptional, (1)
"Wonderful "
United States
Nolufefe Z.
The price is NZ$662
includes taxes & fees
13 Nov - 14 Nov
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
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 favorite 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 depends 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 NZ$249 per night. Entering your travel dates in the search wizard you might find 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?

Newly Renovated Luxury Beach House Ocean Bay Park: This holiday home rental outside of Head of the Harbor is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.