Head of the Harbor Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Head of the Harbor

Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield

3.0 star property
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Outdoor dining
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Vacation Home in Fairfield

10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is ￥31,791
￥78,237 total
includes taxes & fees
Dec 8 - Dec 9
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fridge, microwave, oven, stovetop
Cozy Country Cottage #4

Cottage in Miller Place

10.0 out of 10, Exceptional, (15)
"Lovely cottage with great host! All was wonderful!! very happy with our 17 day vacation!"
United States
Laurita S.
The price is ￥23,262
￥50,497 total
includes taxes & fees
Dec 7 - Dec 8
Cozy Country Cottage #4
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Apartment in 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 ￥16,414
￥43,379 total
includes taxes & fees
Dec 17 - Dec 18
Renovated 2BR Retreat / Modern Comforts Included
Terrace/patio
South Shore Studio in Mastic

Apartment in Mastic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is ￥16,749
￥29,770 total
includes taxes & fees
Dec 14 - Dec 15
South Shore Studio in Mastic
Fridge, microwave, oven, stovetop
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Apartment in Fairfield

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 ￥19,261
￥48,824 total
includes taxes & fees
Dec 17 - Dec 18
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Apartment in Downtown Bridgeport

10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveler
The price is ￥13,182
￥25,395 total
includes taxes & fees
Dec 17 - Dec 18
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Fridge, microwave, oven, stovetop
Cozy Country Cottage #2

Cottage in Miller Place

9.0 out of 10, Wonderful, (15)
"Cottage was awesome!! It was clean and welcoming. We felt at home. Great place to stay."
United States
Bridget
The price is ￥24,813
￥51,031 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy Country Cottage #2
Terrace/patio
The Royal Suite - Ronkonkoma

Vacation Home in Ronkonkoma

2.0 star property
10.0 out of 10, Exceptional, (4)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is ￥12,422
￥46,264 total
includes taxes & fees
Dec 17 - Dec 18
The Royal Suite - Ronkonkoma
Property grounds
3 Story Beach Waterview, 3 KING bed, golf putting green!

Vacation Home in Shirley

10.0 out of 10, Exceptional, (21)
"The place was very well sized and in a lovely location by the beach. Eddie was extremely responsive to all of our questions through out our stay. Would highly recommend!"
United States
Matt H.
The price is ￥27,883
￥94,324 total
includes taxes & fees
Dec 7 - Dec 8
3 Story Beach Waterview, 3 KING bed, golf putting green!
Microwave, oven, stovetop, coffee/tea maker
Peaceful private 2-bedroom house in Bayport.Amazing location!

Vacation Home in Bayport

2.0 star property
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 ￥34,118
￥43,410 total
includes taxes & fees
Dec 17 - Dec 18
Peaceful private 2-bedroom house in Bayport.Amazing location!
2 bedrooms, WiFi, bed sheets
Cozy 2 bedroom retreat in long island

Apartment in Central Islip

2.0 star property
8.0 out of 10, Very Good, (2)
"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 ￥14,888
￥39,336 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 2 bedroom retreat in long island
Smart TV
JC Entire Apartment remodeled, close to Airport and Ferry

Apartment in Coram

10.0 out of 10, Exceptional, (3)
"Would definitely stay again "
United States
Katherine R.
The price is ￥13,182
￥31,008 total
includes taxes & fees
Jan 3 - Jan 4, 2026
JC Entire Apartment remodeled, close to Airport and Ferry
Fridge, microwave, oven, stovetop
Spacious one Bedroom Apt with private entrance

Apartment in Centereach

7.8 out of 10, Good, (10)
"I answered this. Safe and Quit."
United States
John
The price is ￥17,447
￥58,204 total
includes taxes & fees
Dec 14 - Dec 15
Spacious one Bedroom Apt with private entrance
Interior
Sweet Studio w/ Lounge & Pool Table

Apartment in Westport

8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is ￥22,021
￥42,887 total
includes taxes & fees
Dec 17 - Dec 18
Sweet Studio w/ Lounge & Pool Table
Exterior detail
Cozy king suite with kitchen and dining area.

Apartment in Coram

9.4 out of 10, Exceptional, (6)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is ￥27,139
￥40,220 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy king suite with kitchen and dining area.
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Apartment in Kings Park

2.0 star property
10.0 out of 10, Exceptional, (13)
"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 ￥18,842
￥27,730 total
includes taxes & fees
Dec 14 - Dec 15
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2 bedrooms, iron/ironing board, WiFi, bed sheets
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Vacation Home in Stony Brook

2.0 star property
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is ￥35,591
￥82,478 total
includes taxes & fees
Dec 17 - Dec 18
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
Fridge, microwave, oven, stovetop
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Vacation Home in Fairfield

10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is ￥28,506
￥75,742 total
includes taxes & fees
Dec 7 - Dec 8
Bright Escape, Top-Rated Design, Fire pit, Near Beach
1 bedroom, WiFi, bed sheets
Newly renovated Private bedroom near Stony Brook University

Vacation Home in Stony Brook

2.0 star property
8.0 out of 10, Very Good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is ￥17,945
￥38,477 total
includes taxes & fees
Dec 8 - Dec 9
Newly renovated Private bedroom near Stony Brook University
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Head of the Harbor Hotel Reviews

Hyatt Regency Long Island

Hyatt Regency Long Island

10/10 Excellent
"The room was perfect. Staff were beyond wonderful, especially Elizabeth at the front desk"
Joseph 1-night trip
Posted 3 days ago
Hyatt Regency Long Island

Find out more about Head of the Harbor

Search for holiday rentals in Head of the Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Head of the Harbor using one of the methods below:

  • View our selection of featured holiday rentals in Head of the Harbor
  • Use the map to find apartments and other holiday homes in the Head of the Harbor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Head of the Harbor while they last

Look no further and take a look at our great range of rental properties in Head of the Harbor!

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?

Business or Weekend escape: This vacation home rental near Head of the Harbor offers a garden, a barbecue grill, and air-conditioning 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.