Head of the Harbor Vacation Rentals

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Vacation Rentals in Head of the Harbor

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (61)
"Incredible staff, friendly, helpful. "
The price is CA $233
CA $352 total
includes taxes & fees
Aug 14 - Aug 15
DUNE Fairfield Beach

Business or Weekend escape

9.2 out of 10, Wonderful, (42)
"Very nice owner with great communication. "
The price is CA $116
CA $201 total
includes taxes & fees
Jul 29 - Jul 30
Business or Weekend escape

Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

4.8 out of 10, (3)
"Lots of space, great location, suited our extended family well."
Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

2.0 out of 10, (1)
"We went to check in around 5pm since check in was at 4. Luckily we were able to leave our kids with family while we went to check out the place and unload our luggage. We arrived and parked in the street like we were told and walked to the back around the whole yard on an unfinished path. We had to step over a large roof drain pipe to get to the basement door which was not very safe. We went inside turned on the lights and proceeded to check the rooms to find the floors filthy, crumbs were all...
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

8.8 out of 10, Excellent, (27)
"My family rented the unit for two nights while staying at the beach. Great beach access and great l place to see. Shopping eating and night life with in walking distance"
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

LUXURY BAY SHORE HOME

2.0 star property
LUXURY BAY SHORE HOME

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (1)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is CA $155
CA $269 total
includes taxes & fees
Jul 29 - Jul 30
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

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 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is CA $183
CA $318 total
includes taxes & fees
Aug 5 - Aug 6
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

10.0 out of 10, Exceptional, (82)
"Great location. Very peaceful. Great house"
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Walk to Beach 2BR Near Dining & Shopping

6.2 out of 10, (14)
"The home is cute and cozy--located close enough to attractions and restaurants but off the beaten path."
The price is CA $191
CA $422 total
includes taxes & fees
Aug 6 - Aug 7
Walk to Beach 2BR Near Dining & Shopping

3 Story Beach Waterview, 3 KING bed, golf putting green!

9.8 out of 10, Exceptional, (19)
"This place was clean and comfortable, just what we needed."
The price is CA $355
CA $999 total
includes taxes & fees
Aug 13 - Aug 14
3 Story Beach Waterview, 3 KING bed, golf putting green!

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

9.8 out of 10, Exceptional, (19)
"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

10.0 out of 10, Exceptional, (2)
"I was very pleased with the property, and the host made me feel more than welcome."
The price is CA $166
CA $295 total
includes taxes & fees
Aug 4 - Aug 5
Tiny Home Private, Students, Nurses, Tech

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

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 Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

Waterfront & private beach Scandinavian style house near Bellport, NY

9.6 out of 10, Exceptional, (54)
"Beautiful views and a comfortable stay."
Waterfront & private beach Scandinavian style house near Bellport, NY

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

8.8 out of 10, Excellent, (27)
"Nice location close to the ferry"
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

9.0 out of 10, Wonderful, (2)
"Quiet neighborhood, easy checkin, great communication with host. Very clean apartment close to everything. 10/10 recommend. Will book again for next trip"
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard
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

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 is equipped with a barbecue grill, air-conditioning, and WiFi to help you feel comfortable during your stay. 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.