Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Head of the Harbor vacation rentals

Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ￥13,626
￥23,485 total
includes taxes & fees
Apr 1 - Apr 2
Business or Weekend escape
Marina

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, (75 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 ￥32,383
￥74,363 total
includes taxes & fees
Mar 30 - Mar 31
Captain's Cottage - Cold Spring Harbor Water Views
Outdoor dining

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.6 out of 10, Exceptional, (5 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is ￥23,245
￥34,617 total
includes taxes & fees
Apr 6 - Apr 7
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
1 bedroom, desk, iron/ironing board, free WiFi

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, (8 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 ￥22,443
￥36,711 total
includes taxes & fees
Mar 30 - Mar 31
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
1 bedroom, free WiFi, bed sheets

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 ￥21,642
￥35,719 total
includes taxes & fees
Mar 30 - Mar 31
South Shore Studio in Mastic
Exterior

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, (19 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is ￥19,478
￥28,665 total
includes taxes & fees
Mar 31 - Apr 1
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Apartment (4 Bedrooms) | Interior

Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is ￥16,512
￥79,919 total
includes taxes & fees
Mar 30 - Mar 31
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Smart TV, books

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 ￥42,963
￥85,351 total
includes taxes & fees
Mar 30 - Mar 31
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Pool

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 ￥18,516
￥33,619 total
includes taxes & fees
Mar 31 - Apr 1
Tiny Home Private, Students, Nurses, Tech
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is ￥40,023
￥81,625 total
includes taxes & fees
Mar 30 - Mar 31
Modern Vacation home. Close to The Hamptons
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (39 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 ￥15,871
￥26,378 total
includes taxes & fees
Apr 1 - Apr 2
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, WiFi, bed sheets

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.8 out of 10, Excellent, (22 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is ￥14,428
￥26,560 total
includes taxes & fees
Mar 30 - Mar 31
1 bedroom 1 bath private entrance
Terrace/patio

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 ￥25,249
￥63,464 total
includes taxes & fees
Apr 1 - Apr 2
The Royal Suite - Ronkonkoma
Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (83 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ￥26,955
￥40,777 total
includes taxes & fees
Apr 2 - Apr 3
DUNE Fairfield Beach
Terrace/patio

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is ￥56,109
￥154,400 total
includes taxes & fees
Mar 30 - Mar 31
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Smart TV

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is ￥40,078
￥77,110 total
includes taxes & fees
Mar 30 - Mar 31
THE OASIS @ LONG ISLAND
Interior

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 ￥28,054
￥41,943 total
includes taxes & fees
Mar 30 - Mar 31
Cozy king suite with kitchen and dining area.
1 bedroom, WiFi

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 ￥31,260
￥60,991 total
includes taxes & fees
Apr 1 - Apr 2
Luxe Provincial Style Studio w/ Patio & Parking
Dining

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)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is ￥32,222
￥104,584 total
includes taxes & fees
Apr 14 - Apr 15
3 Story Beach Waterview, 3 KING bed, golf putting green!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 ￥17,025
￥28,611 total
includes taxes & fees
Apr 3 - Apr 4
Your Perfect Getaway Between Farmingdale & Amityville
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

Hampton Inn & Suites By Hilton Long Island Farmingdale

Hampton Inn & Suites By Hilton Long Island Farmingdale

10/10 Excellent
"Clean and updated. Friendly staff. Very lively"
David 1-night trip
Posted 2 hours ago
Hampton Inn & Suites By Hilton Long Island Farmingdale

Find out more about Head of the Harbor

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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.