Head of the Harbor Vacation Rentals

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Vacation Rentals in Head of the Harbor

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (68)
"Incredible staff, friendly, helpful. "
$232 nightly
The price is $266
Sep 3 - Sep 4
Total with taxes and fees
DUNE Fairfield Beach

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
$274 nightly
The price is $313
Oct 2 - Oct 3
Total with taxes and fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Business or Weekend escape

9.2 out of 10, Wonderful, (45)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
$130 nightly
The price is $147
Sep 14 - Sep 15
Total with taxes and fees
Business or Weekend escape

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (67)
"Very nice place for a family to stay"
$1,111 nightly
The price is $1,269
Sep 29 - Sep 30
Total with taxes and fees
Newly Renovated Luxury Beach House Ocean Bay Park

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

9.4 out of 10, Exceptional, (26)
"its small but very nice for a short stay would recommend."
$144 nightly
The price is $165
Sep 2 - Sep 3
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

10.0 out of 10, Exceptional, (58)
"From the moment we booked this trip we knew we were in for a treat. Windows on the Sea did not disappoint! From the early communication with our hosts and their thoughtful check-ins leading up to our trip, this was the best experience we could ask for. We highly recommend staying here!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

Walk to Beach 2BR Near Dining & Shopping

6.4 out of 10, (19)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
$267 nightly
The price is $304
Sep 2 - Sep 3
Total with taxes and fees
Walk to Beach 2BR Near Dining & Shopping

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (19)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

$935 nightly
The price is $1,068
Sep 8 - Sep 9
Total with taxes and fees
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

9.8 out of 10, Exceptional, (21)
"Great time...close to the beach or the bay"
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

Tiny Home Private, Students, Nurses, Tech

9.4 out of 10, Exceptional, (3)
"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!"
$190 nightly
The price is $198
Sep 2 - Sep 3
Total with taxes and fees
Tiny Home Private, Students, Nurses, Tech

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Charming 4 bedroom home with pool, basketball court, in superb East Patchogue

10.0 out of 10, Exceptional, (1)
"Nice house and great pool. "
$2,570 nightly
The price is $2,936
Sep 29 - Sep 30
Total with taxes and fees
Charming 4 bedroom home with pool, basketball court, in superb East Patchogue

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (48)
"We've stayed here twice when visiting family in town, it's a lovely space and very welcoming."
1856 Trading House w/ walk to water

Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

9.2 out of 10, Wonderful, (15)
"The property was very quaint and comfortable. We'll probably stay again in the future"
$143 nightly
The price is $150
Sep 2 - Sep 3
Total with taxes and fees
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

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

9.0 out of 10, Wonderful, (53)
"Has a very nice stay."
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

1 bedroom 1 bath private entrance

8.8 out of 10, Excellent, (20)
"Augustine was very helpful and nice!It was a great price that enabled us to visit friends and family for the holidays "
$181 nightly
The price is $207
Sep 2 - Sep 3
Total with taxes and fees
1 bedroom 1 bath private entrance

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (2)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
$200 nightly
The price is $227
Sep 2 - Sep 3
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Charming 1-bedroom house in lovely Stony Brook with AC

Charming 1-bedroom house in lovely Stony Brook with AC
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

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 $147 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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This vacation home rental near Head of the Harbor has air-conditioning and a Smart TV 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 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.