Head of the Harbor Holiday Rentals

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Our top choices for Head of the Harbor holiday rentals

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, (38 reviews)
"We had a good experience and we brought our little pup and she was welcome there. Clean and quiet stay "
United States
janice s.
The price is NZ$280
includes taxes & fees
19 Feb - 20 Feb
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"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$476
includes taxes & fees
19 Feb - 20 Feb
Renovated 2BR Retreat / Modern Comforts Included

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, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is NZ$301
includes taxes & fees
24 Feb - 25 Feb
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
8.6 out of 10, Excellent, (7 reviews)
"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$329
includes taxes & fees
22 Feb - 23 Feb
Tiny Home Private, Students, Nurses, Tech

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"My husband, two boys (6 & 11) and I stayed in this quaint, little, clean apartment for four nights. They provided coffee, creamer and bathroom necessities. It was perfect for a short stay. When we did need something the owner was quick to reply and get it to us. If need be we will stay here again."
United States
NATALIE P.
The price is NZ$549
includes taxes & fees
19 Feb - 20 Feb
Spacious one Bedroom Apt with private entrance

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is NZ$370
includes taxes & fees
19 Feb - 20 Feb
South Shore Studio in Mastic

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
9.6 out of 10, Exceptional, (7 reviews)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is NZ$380
includes taxes & fees
20 Feb - 21 Feb
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is NZ$242
includes taxes & fees
1 Mar - 2 Mar
Business or Weekend escape

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 reviews)
"Would definitely stay again "
United States
Katherine R.
The price is NZ$331
includes taxes & fees
28 Feb - 1 Mar
JC Entire Apartment remodeled, close to Airport and Ferry

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.4 out of 10, Exceptional, (6 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is NZ$436
includes taxes & fees
19 Feb - 20 Feb
Cozy king suite with kitchen and dining area.

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

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is NZ$882
includes taxes & fees
19 Feb - 20 Feb
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic! Well communicated and perfectly described! Highly recommend and thank you!"
United States
Wayne L.
The price is NZ$354
includes taxes & fees
19 Feb - 20 Feb
Your Perfect Getaway Between Farmingdale & Amityville

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$561
includes taxes & fees
1 Mar - 2 Mar
The Royal Suite - Ronkonkoma

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is NZ$616
includes taxes & fees
24 Feb - 25 Feb
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

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 reviews)
"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$1,029
includes taxes & fees
25 Feb - 26 Feb
3 Story Beach Waterview, 3 KING bed, golf putting green!

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is NZ$769
includes taxes & fees
23 Feb - 24 Feb
Captain's Cottage - Cold Spring Harbor Water Views

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 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 NZ$623
includes taxes & fees
19 Feb - 20 Feb
Luxe Provincial Style Studio w/ Patio & Parking

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 review)
"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$515
includes taxes & fees
24 Feb - 25 Feb
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Cozy Modern Gateway

Cozy Modern Gateway
Centereach
The price is NZ$284
includes taxes & fees
19 Feb - 20 Feb
Cozy Modern Gateway
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$242 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.