Head of the Harbor Holiday Rentals from €124: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Head of the Harbor has to offer?

Large Beach House Steps From Town and Ocean : This holiday home rental outside of Head of the Harbor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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In two weeks

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Our top choices for Head of the Harbor holiday rentals

A two-story house with a front porch, a small garden with various plants, and a tree with red leaves.

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

Kings Park

Karen D.

includes taxes & fees

17 Sept - 18 Sept

A compact kitchen with dark cabinets, stainless appliances, and a tiled floor.

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

Centereach

Amanda

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, a nightstand, a mirror, and a window with curtains.

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

Brentwood

Jaelyn

includes taxes & fees

22 Sept - 23 Sept

A spacious living area with a stone fireplace, marble flooring, and a staircase leading to another room.

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

Setauket- East Setauket

"While we received multiple confirmations of our reservation, including the morning we were to check in, the property manager never sent us check in instructions, even after we emailed asking for them. Then, after spending over an hour with multiple calls to VRBO customer service, who also couldn’t get ahold of the property manager, we arrived at the location. There was a 4ft high, 10ft wide heap of garbage in the front yard and looking in through the windows it was apparent the house was under...

Lisa F.

includes taxes & fees

22 Sept - 23 Sept

A white shelving unit with decorative items, including a mixtape box, two golden bird figurines, and three glass vases.

5. Sundown Escape-South Shore Long Island

Bay Shore

Samantha

includes taxes & fees

22 Sept - 23 Sept

A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

6. The Royal Suite - Ronkonkoma

Ronkonkoma

Maureen F.

includes taxes & fees

21 Sept - 22 Sept

A wooden deck with a white railing, a stone pathway, and a white fence in the background.

7. Spacious 3BR Family Home Near Everything

Central Islip

includes taxes & fees

5 Oct - 6 Oct

A living room with a brown sofa, a glass coffee table with decorative items, and a kitchen in the background with wooden cabinets and a black refrigerator.

8. Spacious one Bedroom Apt with private entrance

Centereach

Selective Travel M.

includes taxes & fees

22 Sept - 23 Sept

A house with a white exterior, a brown roof, and a balcony. It is located on stilts over water, surrounded by dense green trees.

9. Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery

Northport

Anonymous traveller

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

10. DUNE Fairfield Beach

Fairfield Beach

slava

includes taxes & fees

28 Sept - 29 Sept

A room with a white door, a sign reading "Relax", a potted plant, and a small table with a sign and a lamp.

11. Cozy king suite with kitchen and dining area.

Coram

Tasia P.

includes taxes & fees

21 Sept - 22 Sept

A hot tub with water jets, a television displaying a beach scene, and a sign on the wall.

12. THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

Commack

Kenneth B.

includes taxes & fees

12 Oct - 13 Oct

A living room with a blue door, a white shelf, a grey sofa with patterned cushions, and a small table with a decorative item.

13. Bright & Comfortable Home in the Heart of It All

Central Islip

"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"

Tatiana J.

includes taxes & fees

30 Sept - 1 Oct

14. Welcoming 1 bedroom apartment in beautiful harbor village.

Northport

Sallyann S.

includes taxes & fees

22 Sept - 23 Sept

A wooden deck with chairs and a kayak, leading to a beach with a view of the ocean.

15. Shore to Shore Coastal Retreat at Asharoken

Northport

"We had a great time at this Vrbo. The house is spacious and the backyard absolutely beautiful. We brought two babies under 2 and it was a perfect spot. The private beach is just steps away and lovely for low-key beach days. The fridge was not working properly, and Joe let us know ahead of time and provided us with a mini fridge that worked, which made everything easy. He also ordered us more paper towels and dish soap while we were there which was super helpful and accomodating. Would absolutely...

Rachel W.

includes taxes & fees

21 Sept - 22 Sept

A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

16. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Rocky Point

ken g.

includes taxes & fees

17 Sept - 18 Sept

A modern living room with a grey sofa, a wooden coffee table, a flat-screen TV mounted on the wall, and a ceiling light fixture.

17. Peaceful private 2-bedroom house in Bayport. Amazing location!

Bayport

Rowena V.

includes taxes & fees

6 Oct - 7 Oct

A dining area with a white table, gold chairs, and a potted plant.

18. The Bay House Patchogue Bay & Town 10 Minutes Walk

Patchogue

Adam B.

includes taxes & fees

9 Oct - 10 Oct

A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

19. Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor

Daniel M.

includes taxes & fees

21 Sept - 22 Sept

A water park with multiple slides and pools, surrounded by trees and a parking lot.

20. Tiny Home Private, Students, Nurses, Tech

Bay Shore

Brian C.

includes taxes & fees

17 Sept - 18 Sept

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Top Head of the Harbor Hotel Reviews

Hilton Garden Inn Melville

10/10 Excellent

"Room was spotless. The food for breakfast and evening was very good. The staff were Very personable."

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, apart-hotels, 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 €124 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?

Large Beach House Steps From Town and Ocean: This holiday home rental outside of Head of the Harbor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.

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Check prices for these dates

Our top choices for Head of the Harbor holiday rentals

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

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

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

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