Head of the Harbor Vacation Rentals

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Check prices for these dates

Tonight
Sep 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

Vacation Rentals in Head of the Harbor

Our top choices for Head of the Harbor vacation rentals

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

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (68)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Beach

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is ￥39,233
￥53,960 total
includes taxes & fees
Oct 1 - Oct 2
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Business or Weekend escape
Pool

Business or Weekend escape

9.2 out of 10, Wonderful, (46)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
The price is ￥12,584
￥21,689 total
includes taxes & fees
Sep 14 - Sep 15
Business or Weekend escape
Newly Renovated Luxury Beach House Ocean Bay Park
Outdoor dining

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (67)
"Very nice place for a family to stay"
The price is ￥103,487
￥185,385 total
includes taxes & fees
Sep 29 - Sep 30
Newly Renovated Luxury Beach House Ocean Bay Park
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

9.4 out of 10, Exceptional, (26)
"its small but very nice for a short stay would recommend."
The price is ￥14,657
￥24,360 total
includes taxes & fees
Sep 5 - Sep 6
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Terrace/patio

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
Outdoor pool, a heated pool

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

10.0 out of 10, Exceptional, (58)
"From the moment we booked this trip we knew we were in for a treat. Windows on the Sea did not disappoint! From the early communication with our hosts and their thoughtful check-ins leading up to our trip, this was the best experience we could ask for. We highly recommend staying here!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
Walk to Beach 2BR Near Dining & Shopping
Property grounds

Walk to Beach 2BR Near Dining & Shopping

6.4 out of 10, (19)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is ￥20,653
￥45,078 total
includes taxes & fees
Sep 7 - Sep 8
Walk to Beach 2BR Near Dining & Shopping
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Dining

Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

9.2 out of 10, Wonderful, (15)
"The property was very quaint and comfortable. We'll probably stay again in the future"
The price is ￥12,214
￥22,193 total
includes taxes & fees
Sep 5 - Sep 6
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (19)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC
Microwave, oven, stovetop, dishwasher

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

The price is ￥118,440
￥158,154 total
includes taxes & fees
Sep 11 - Sep 12
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!
Beach nearby

Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

9.8 out of 10, Exceptional, (21)
"Great time...close to the beach or the bay"
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!
Tiny Home Private, Students, Nurses, Tech
Property grounds

Tiny Home Private, Students, Nurses, Tech

9.4 out of 10, Exceptional, (3)
"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!"
The price is ￥15,471
￥29,666 total
includes taxes & fees
Sep 6 - Sep 7
Tiny Home Private, Students, Nurses, Tech
Modern Vacation home. Close to The Hamptons
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is ￥49,227
￥93,287 total
includes taxes & fees
Sep 5 - Sep 6
Modern Vacation home. Close to The Hamptons
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Beach

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Charming 4 bedroom home with pool, basketball court, in superb East Patchogue
Interior

Charming 4 bedroom home with pool, basketball court, in superb East Patchogue

10.0 out of 10, Exceptional, (1)
"Nice house and great pool. "
The price is ￥318,308
￥434,709 total
includes taxes & fees
Sep 29 - Sep 30
Charming 4 bedroom home with pool, basketball court, in superb East Patchogue
1856 Trading House w/ walk to water
Smart TV, DVD player, books

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (48)
"We've stayed here twice when visiting family in town, it's a lovely space and very welcoming."
1856 Trading House w/ walk to water
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Fridge, microwave, oven, stovetop

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

9.0 out of 10, Wonderful, (53)
"Has a very nice stay."
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Charming 3-bedroom modern family retreat!
Property grounds

Charming 3-bedroom modern family retreat!

10.0 out of 10, Exceptional, (1)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is ￥51,033
￥76,404 total
includes taxes & fees
Sep 7 - Sep 8
Charming 3-bedroom modern family retreat!
1 bedroom 1 bath private entrance
Interior

1 bedroom 1 bath private entrance

8.8 out of 10, Excellent, (20)
"Augustine was very helpful and nice!It was a great price that enabled us to visit friends and family for the holidays "
The price is ￥18,654
￥30,953 total
includes taxes & fees
Sep 7 - Sep 8
1 bedroom 1 bath private entrance
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

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:

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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?

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.: 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 dishwasher, a stovetop, and a microwave.

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.