Head of the Harbor Holiday Rentals

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Our top choices for Head of the Harbor holiday rentals

10.0 out of 10, Exceptional, (1 review)
"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 AU$2,938
includes taxes & fees
26 Jan - 27 Jan
The Bella Vista St James! Waterfront house with a beach dock and so much more!
8.4 out of 10, Very good, (6 reviews)
"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 AU$294
includes taxes & fees
26 Jan - 27 Jan
Tiny Home Private, Students, Nurses, Tech
The price is AU$240
includes taxes & fees
24 Jan - 25 Jan
Cozy 1-bedroomwith 1 Extra sleep mobile home in awesome Deer Park with AC & More
10.0 out of 10, Exceptional, (3 reviews)
"Would definitely stay again "
United States
Katherine R.
The price is AU$295
includes taxes & fees
26 Jan - 27 Jan
JC Entire Apartment remodeled, close to Airport and Ferry

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2 reviews)
"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$417
includes taxes & fees
5 Feb - 6 Feb
Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is AU$311
includes taxes & fees
2 Feb - 3 Feb
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Apartment in Mastic

South Shore Studio in Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is AU$332
includes taxes & fees
28 Jan - 29 Jan
South Shore Studio in Mastic
10.0 out of 10, Exceptional, (17 reviews)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is AU$269
includes taxes & fees
5 Feb - 6 Feb
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (1 review)
"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$460
includes taxes & fees
24 Jan - 25 Jan
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
9.4 out of 10, Exceptional, (37 reviews)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is AU$227
includes taxes & fees
26 Jan - 27 Jan
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Holiday Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$217
includes taxes & fees
2 Feb - 3 Feb
Business or Weekend escape
7.8 out of 10, Good, (10 reviews)
"I answered this. Safe and Quit."
United States
John
The price is AU$498
includes taxes & fees
26 Jan - 27 Jan
Spacious one Bedroom Apt with private entrance
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is AU$902
includes taxes & fees
28 Jan - 29 Jan
3 Story Beach Waterview, 3 KING bed, golf putting green!

Apartment in Central Islip

Cozy 2 bedroom retreat in long island
7.0 out of 10, Good, (4 reviews)
"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$395
includes taxes & fees
26 Jan - 27 Jan
Cozy 2 bedroom retreat in long island

Holiday Home in East Patchogue

Pure Paradise Hamptons Getaway
10.0 out of 10, Exceptional, (1 review)
"Nice house and great pool. "
United States
Bret C.
The price is AU$2,885
includes taxes & fees
28 Jan - 29 Jan
Pure Paradise Hamptons Getaway

Apartment in Bay Shore

1 bedroom 1 bath private entrance
8.8 out of 10, Excellent, (22 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is AU$290
includes taxes & fees
28 Jan - 29 Jan
1 bedroom 1 bath private entrance
10.0 out of 10, Exceptional, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is AU$693
includes taxes & fees
5 Feb - 6 Feb
Bright Escape, Top-Rated Design, Fire pit, Near Beach
9.4 out of 10, Exceptional, (6 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is AU$390
includes taxes & fees
26 Jan - 27 Jan
Cozy king suite with kitchen and dining area.
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful inside and out. The host was very responsive. The furnishings where comfortable. Area was very nice with the pond. Although there was a canoe availabe we didnt use dew to our age.lol there where other amenities we didnt use either fire pit a barbecue grill and other outdoor zen spots. We highly recomend this host."
United States
Gregory D.
The price is AU$435
includes taxes & fees
31 Jan - 1 Feb
Lakefront GetawaY & Romantic NightS + BeacheS NeaR
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$217 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?

The Bella Vista St James! Waterfront house with a beach dock and so much more!: This highly rated holiday home rental in Head of the Harbor is located on the beach, and has a fireplace, a balcony 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. You can relax into your holiday with a garden and 1 hot tub.

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.