Head of the Harbor Holiday Rentals

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Holiday Rentals in Head of the Harbor

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (71)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

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

9.4 out of 10, Exceptional, (29)
"its small but very nice for a short stay would recommend."
The price is NZ$285
includes taxes & fees
29 Sept - 30 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

“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. "
The price is NZ$573
includes taxes & fees
2 Oct - 3 Oct
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (71)
"Very nice place for a family to stay"
The price is NZ$2,045
includes taxes & fees
8 Oct - 9 Oct
Newly Renovated Luxury Beach House Ocean Bay Park

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
The price is NZ$1,220
includes taxes & fees
10 Oct - 11 Oct
Spacious Home Located Close to Stony Brook!

Business or Weekend escape

9.2 out of 10, Wonderful, (46)
"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. "
The price is NZ$254
includes taxes & fees
28 Sept - 29 Sept
Business or Weekend escape

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

9.0 out of 10, Wonderful, (16)
"The property was very quaint and comfortable. We'll probably stay again in the future"
The price is NZ$260
includes taxes & fees
3 Oct - 4 Oct
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

8.8 out of 10, Excellent, (8)
"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

Tiny Home Private, Students, Nurses, Tech

9.0 out of 10, Wonderful, (4)
"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!"
The price is NZ$351
includes taxes & fees
29 Sept - 30 Sept
Tiny Home Private, Students, Nurses, Tech

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"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. "
The price is NZ$478
includes taxes & fees
29 Sept - 30 Sept
Walk to Beach 2BR Near Dining & Shopping

Charming 3-bedroom modern family retreat!

9.0 out of 10, Wonderful, (4)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is NZ$857
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom modern family retreat!

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 "
The price is NZ$344
includes taxes & fees
3 Oct - 4 Oct
1 bedroom 1 bath private entrance

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is NZ$1,084
includes taxes & fees
6 Oct - 7 Oct
Modern Vacation home. Close to The Hamptons

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 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (8)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is NZ$401
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house with WiFi, AC in Fairfield

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (10)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is NZ$1,640
includes taxes & fees
30 Sept - 1 Oct
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

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!

Luxury and Affordable Family Home

7.4 out of 10, Good, (8)
"My family and I had the pleasure of staying here during the Christmas holidays, and it was an excellent experience. We were especially grateful for the accessibility features, as my grandmother (85 years young), who uses a walker and had recently undergone surgery, was able to comfortably stay on the main floor. The property had just a few steps to enter, and best of all, there was a bedroom and full bathroom on the main level, along with ample room for a walker or wheelchair.The home itself was...
The price is NZ$1,639
includes taxes & fees
29 Sept - 30 Sept
Luxury and Affordable Family Home

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (67)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (39)
"Great place to stay. It was prefect for our family of six. We really enjoyed the stay and would stay there again. It was very clean and organized."
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
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 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$254 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?

Spacious Home Located Close to Stony Brook!: This holiday home rental outside of Head of the Harbor offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable 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.