Head of the Harbor Holiday Rentals

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Our top choices for Head of the Harbor holiday rentals

The Bella Vista St James! Waterfront house with a beach dock and so much more!

The Bella Vista St James! Waterfront house with a beach dock and so much more!
Saint James
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.
The price is NZ$3,566
includes taxes & fees
4 Jan - 5 Jan
The Bella Vista St James! Waterfront house with a beach dock and so much more!

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
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.
The price is NZ$350
includes taxes & fees
4 Jan - 5 Jan
Tiny Home Private, Students, Nurses, Tech

Cozy 1-bedroomwith 1 Extra sleep mobile home in awesome Deer Park with AC & More

Cozy 1-bedroomwith 1 Extra sleep mobile home in awesome Deer Park with AC & More
2.0 star property
Deer Park
The price is NZ$250
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroomwith 1 Extra sleep mobile home in awesome Deer Park with AC & More

DUNE Fairfield Beach

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

JC Entire Apartment remodeled, close to Airport and Ferry

JC Entire Apartment remodeled, close to Airport and Ferry
Coram
10.0 out of 10, Exceptional, (3)
"Would definitely stay again "
United States
Katherine R.
The price is NZ$347
includes taxes & fees
15 Jan - 16 Jan
JC Entire Apartment remodeled, close to Airport and Ferry

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2)
"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 NZ$501
includes taxes & fees
15 Jan - 16 Jan
Renovated 2BR Retreat / Modern Comforts Included

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
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.
The price is NZ$543
includes taxes & fees
27 Jan - 28 Jan
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Cozy 2 bedroom retreat in long island

Cozy 2 bedroom retreat in long island
2.0 star property
Central Islip
8.8 out of 10, Excellent, (3)
"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 NZ$461
includes taxes & fees
5 Jan - 6 Jan
Cozy 2 bedroom retreat in long island

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (4)
"Nice little spot with a great host."
United States
J M.
The price is NZ$366
includes taxes & fees
7 Jan - 8 Jan
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma

Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma
2.0 star property
Ronkonkoma
The price is NZ$240
includes taxes & fees
15 Jan - 16 Jan
Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma

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

Peaceful private 2-bedroom house in Bayport.Amazing location!
2.0 star property
Bayport
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is NZ$387
includes taxes & fees
4 Jan - 5 Jan
Peaceful private 2-bedroom house in Bayport.Amazing location!

South Shore Studio in Mastic

South Shore Studio in Mastic
2.0 star property
Mastic
10.0 out of 10, Exceptional, (3)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is NZ$392
includes taxes & fees
17 Jan - 18 Jan
South Shore Studio in Mastic

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
6.8 out of 10, (26)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is NZ$391
includes taxes & fees
15 Jan - 16 Jan
Walk to Beach 2BR Near Dining & Shopping

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22)
"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 NZ$1,078
includes taxes & fees
11 Jan - 12 Jan
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy and Modern 2-bedroom apartment in lovely Yaphank

Cozy and Modern 2-bedroom apartment in lovely Yaphank
2.0 star property
Yaphank
10.0 out of 10, Exceptional, (1)
The price is NZ$726
includes taxes & fees
4 Jan - 5 Jan
Cozy and Modern 2-bedroom apartment in lovely Yaphank

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is NZ$254
includes taxes & fees
2 Feb - 3 Feb
Business or Weekend escape

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
Kings Park
10.0 out of 10, Exceptional, (17)
"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 NZ$315
includes taxes & fees
15 Jan - 16 Jan
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is NZ$662
includes taxes & fees
11 Jan - 12 Jan
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10)
"I answered this. Safe and Quit."
United States
John
The price is NZ$587
includes taxes & fees
15 Jan - 16 Jan
Spacious one Bedroom Apt with private entrance

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach
Fairfield
10.0 out of 10, Exceptional, (11)
"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 NZ$834
includes taxes & fees
4 Jan - 5 Jan
Bright Escape, Top-Rated Design, Fire pit, Near Beach
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 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?

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.