Head of the Harbor Vacation Rentals

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Vacation Rentals in Head of the Harbor

The Bella Vista St James! Waterfront house with a beach dock and so much more!
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.
$1,844 nightly
The price is $2,107
Nov 1 - Nov 2
Total with taxes and fees
The Bella Vista St James! Waterfront house with a beach dock and so much more!
Tiny Home Private, Students, Nurses, Tech
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.
$204 nightly
The price is $213
Oct 31 - Nov 1
Total with taxes and fees
Tiny Home Private, Students, Nurses, Tech
Private Queen BedRm, Events, PetPally, LTR, MTR, STR
9.8 out of 10, Exceptional, (7)
"Lovely seconfloor bedroom, close to many town amenities. Property garded by a lovely flock of chickens. I love the place. !!!!"
United States
Horacio R C.
$146 nightly
The price is $154
Oct 31 - Nov 1
Total with taxes and fees
Private Queen BedRm, Events, PetPally, LTR, MTR, STR
The Royal Suite - 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.
$257 nightly
The price is $293
Nov 3 - Nov 4
Total with taxes and fees
The Royal Suite - Ronkonkoma
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
9.0 out of 10, Wonderful, (18)
"Clean and quiet little place convenient to many industrial parks. "
United States
Bradley C.
$159 nightly
The price is $167
Nov 3 - Nov 4
Total with taxes and fees
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (75)
"Loved this venue! "
United States
adriano
$232 nightly
The price is $267
Nov 10 - Nov 11
Total with taxes and fees
DUNE Fairfield Beach
Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (1)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
$255 nightly
The price is $289
Nov 2 - Nov 3
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
$145 nightly
The price is $164
Nov 1 - Nov 2
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Business or Weekend escape
9.2 out of 10, Wonderful, (50)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$125 nightly
The price is $141
Nov 2 - Nov 3
Total with taxes and fees
Business or Weekend escape
Cozy 2 bedroom retreat in long island
2.0 star property
$193 nightly
The price is $221
Oct 31 - Nov 1
Total with taxes and fees
Cozy 2 bedroom retreat in long island
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
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.
$279 nightly
The price is $316
Nov 2 - Nov 3
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Sweet Studio w/ Lounge & Pool Table
8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
$223 nightly
The price is $253
Nov 16 - Nov 17
Total with taxes and fees
Sweet Studio w/ Lounge & Pool Table
Spacious one Bedroom Apt with private entrance
8.4 out of 10, Very Good, (9)
"I answered this. Safe and Quit."
United States
John
$328 nightly
The price is $374
Nov 2 - Nov 3
Total with taxes and fees
Spacious one Bedroom Apt with private entrance
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
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
$157 nightly
The price is $179
Nov 3 - Nov 4
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Newly renovated Private bedroom near Stony Brook University
2.0 star property
6.0 out of 10, (1)
"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
$203 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
Newly renovated Private bedroom near Stony Brook University
Cozy Country Cottage #4
10.0 out of 10, Exceptional, (15)
"Very calming property and everything you would need inside. "
United States
Aimee L.
$279 nightly
The price is $319
Oct 31 - Nov 1
Total with taxes and fees
Cozy Country Cottage #4
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.6 out of 10, Exceptional, (32)
"This studio is so cute and cozy."
United States
Michelle H.
$144 nightly
The price is $165
Nov 2 - Nov 3
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
3 Story Beach Waterview, 3 KING bed, golf putting green!
10.0 out of 10, Exceptional, (21)
"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.
$553 nightly
The price is $632
Nov 12 - Nov 13
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!
Your Perfect Getaway Between Farmingdale & Amityville
10.0 out of 10, Exceptional, (1)
"Fantastic! Well communicated and perfectly described! Highly recommend and thank you!"
United States
Wayne L.
$174 nightly
The price is $199
Nov 8 - Nov 9
Total with taxes and fees
Your Perfect Getaway Between Farmingdale & Amityville
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Head of the Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Head of the Harbor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Head of the Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 vacation rentals in Head of the Harbor?

Yes, we offer vacation rentals close to top attractions in Head of the Harbor, or you can choose a more remote option if you'd like a relaxing place to stay. Head of the Harbor is known for its wineries and parks.

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

Newly Renovated Luxury Beach House Ocean Bay Park: This vacation home rental near Head of the Harbor is located near the beach and has a patio, a selection of games, and a barbecue grill 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 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 vacation rentals like in Head of the Harbor?

Vacation rentals are private accommodations you can reserve for several days or longer in Head of the Harbor. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family gatherings.