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Head of the Harbor Vacation Rentals

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Our top choices for Head of the Harbor vacation rentals

Waterfront Paradise Private Beach + Dock + Hot tub

Waterfront Paradise Private Beach + Dock + Hot tub
Saint James
10.0 out of 10, Exceptional, (1 review)
"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 CA $1,413
CA $2,669 total
includes taxes & fees
Jul 22 - Jul 23
Waterfront Paradise Private Beach + Dock + Hot tub

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is CA $170
CA $251 total
includes taxes & fees
Jul 20 - Jul 21
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

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

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (28 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is CA $202
CA $352 total
includes taxes & fees
Aug 2 - Aug 3
Private 1 bedroom apt in a quiet neighborhood, close to all!

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

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (46 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is CA $158
CA $252 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (7 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is CA $146
CA $464 total
includes taxes & fees
Jul 30 - Jul 31
The Royal Suite - Ronkonkoma

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is CA $158
CA $481 total
includes taxes & fees
Jul 21 - Jul 22
Spacious one Bedroom Apt with private entrance

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is CA $190
CA $425 total
includes taxes & fees
Jul 22 - Jul 23
Sundown Escape-South Shore Long Island

Cozy Country Cottage #4

Cozy Country Cottage #4
Miller Place
9.6 out of 10, Exceptional, (16 reviews)
"Great stay"
United States
Susan W.
The price is CA $266
CA $529 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Country Cottage #4

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is CA $302
CA $484 total
includes taxes & fees
Jul 22 - Jul 23
Spacious 3BR Family Home Near Everything

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is CA $245
CA $376 total
includes taxes & fees
Jul 20 - Jul 21
Cozy king suite with kitchen and dining area.

Cozy Country Cottage #2

Cozy Country Cottage #2
Miller Place
9.2 out of 10, Wonderful, (17 reviews)
"Great place to stay, clean, location is close to everything, bed is oh, so comfortable. Love this cottage it is my home away from home. "
United States
Lillian D.
The price is CA $308
CA $583 total
includes taxes & fees
Jul 30 - Jul 31
Cozy Country Cottage #2

Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
10.0 out of 10, Exceptional, (2 reviews)
"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!"
United States
Tatiana J.
The price is CA $261
CA $718 total
includes taxes & fees
Jul 27 - Jul 28
Bright & Comfortable Home in the Heart of It All

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (100 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is CA $251
CA $374 total
includes taxes & fees
Aug 19 - Aug 20
DUNE Fairfield Beach

Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
The price is CA $151
CA $287 total
includes taxes & fees
Jul 21 - Jul 22
Welcoming 1 bedroom apartment in beautiful harbor village.

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (24 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is CA $164
CA $277 total
includes taxes & fees
Jul 23 - Jul 24
1 bedroom 1 bath private entrance

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is CA $158
CA $276 total
includes taxes & fees
Jul 20 - Jul 21
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is CA $202
CA $480 total
includes taxes & fees
Jul 22 - Jul 23
Sundown Escape Near SouthShore University Hospital

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (4 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is CA $273
CA $540 total
includes taxes & fees
Jul 20 - Jul 21
Luxe Provincial Style Studio w/ Patio & Parking

3-bedroom cozy home in wonderful Selden , Great location close to all.

3-bedroom cozy home in wonderful Selden , Great location close to all.
Selden
10.0 out of 10, Exceptional, (3 reviews)
"Lovely home. Very comfortable. Didn’t get to enjoy the outside but would definitely come again "
United States
Fran H.
The price is CA $559
CA $1,259 total
includes taxes & fees
Aug 9 - Aug 10
3-bedroom cozy home in wonderful Selden , Great location close to all.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Head of the Harbor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Stony Brook Grist Mill and Harmony Vineyards.

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.