Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Head of the Harbor vacation rentals

Smart TV

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 ￥13,502
￥32,307 total
includes taxes & fees
Jun 13 - Jun 14
JC Entire Apartment remodeled, close to Airport and Ferry
Luxury Room, 1 King Bed, Non Smoking, Air conditioning | Living area | Fireplace

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is ￥22,237
￥41,132 total
includes taxes & fees
May 25 - May 26
Spacious 3BR Family Home Near Everything
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (54 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ￥13,502
￥23,271 total
includes taxes & fees
May 25 - May 26
Business or Weekend escape
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 ￥23,351
￥87,177 total
includes taxes & fees
May 29 - May 30
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
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, (89 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ￥28,001
￥41,891 total
includes taxes & fees
May 26 - May 27
DUNE Fairfield Beach
Exterior

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 ￥22,884
￥49,737 total
includes taxes & fees
May 24 - May 25
Sundown Escape-South Shore Long Island
TV

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 ￥17,871
￥54,535 total
includes taxes & fees
May 24 - May 25
Spacious one Bedroom Apt with private entrance
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, (40 reviews)
"I found everything to be clean and fresh. Owners were nice. I would stay there again. "
United States
Mark
The price is ￥16,870
￥27,443 total
includes taxes & fees
May 26 - May 27
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Pool

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
7.8 out of 10, Good, (8 reviews)
"Great host, nice place."
United States
Brian C.
The price is ￥20,997
￥37,034 total
includes taxes & fees
Jun 3 - Jun 4
Tiny Home Private, Students, Nurses, Tech
Property grounds

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
6.8 out of 10, (28 reviews)
"Host was very welcoming and helpful! "
United States
Alissa I.
The price is ￥17,871
￥44,011 total
includes taxes & fees
May 25 - May 26
Walk to Beach 2BR Near Dining & Shopping
TV, fireplace, offices

Renovated 3BR Apt / Easy Check-In / FamilyFriendly

Renovated 3BR Apt / Easy Check-In / FamilyFriendly
West End - West Side
The price is ￥20,244
￥54,575 total
includes taxes & fees
May 27 - May 28
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
1 bedroom, free WiFi, bed sheets

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (4 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is ￥21,445
￥36,118 total
includes taxes & fees
May 25 - May 26
South Shore Studio in Mastic
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 ￥42,572
￥86,753 total
includes taxes & fees
Jun 1 - Jun 2
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
House (3 Bedrooms) | Interior

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Rocky Point
The price is ￥52,103
￥97,823 total
includes taxes & fees
May 24 - May 25
Charming Rocky Point Home ~ 1 Mi to Beach!
Iron/ironing board, internet, bed sheets

Wonderful 3-bedroom apartment with AC in welcoming Bridgeport

Wonderful 3-bedroom apartment with AC in welcoming Bridgeport
Downtown Bridgeport
The price is ￥30,595
￥44,675 total
includes taxes & fees
May 26 - May 27
Wonderful 3-bedroom apartment with AC in welcoming Bridgeport
Dining

Pure Paradise Hamptons Getaway

Pure Paradise Hamptons Getaway
East Patchogue
10.0 out of 10, Exceptional, (1 review)
"Nice house and great pool. "
United States
Bret C.
The price is ￥262,103
￥388,743 total
includes taxes & fees
May 22 - May 23
Pure Paradise Hamptons Getaway
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 ￥39,713
￥77,859 total
includes taxes & fees
Jun 3 - Jun 4
THE OASIS @ LONG ISLAND
1 bedroom, desk, WiFi, bed sheets

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥22,557
￥42,143 total
includes taxes & fees
May 25 - May 26
Spacious Studio with Pool Table
1 bedroom, iron/ironing board, free WiFi, bed sheets

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.6 out of 10, Exceptional, (4 reviews)
"It was relaxing very comfortable "
United States
Julian R.
The price is ￥16,870
￥34,339 total
includes taxes & fees
May 25 - May 26
Your Perfect Getaway Between Farmingdale & Amityville
Interior

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, (26 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 ￥25,416
￥43,557 total
includes taxes & fees
Jun 7 - Jun 8
Private 1 bedroom apt in a quiet neighborhood, 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

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

10/10 Excellent
"Nothing I would stay again no problem"
Daniel 4-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

Find out more about Head of the Harbor

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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 WiFi 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 Harmony Vineyards and Stony Brook Grist Mill.

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.