Head of the Harbor Holiday Rentals

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Holiday Rentals in Head of the Harbor

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (60)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Business or Weekend escape

9.2 out of 10, Wonderful, (40)
"Very nice owner with great communication. "
The price is NZ$245
includes taxes & fees
20 July - 21 July
Business or Weekend escape

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...
The price is NZ$385
includes taxes & fees
3 Aug - 4 Aug
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

(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

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

Quiet Bayside cottage. 10 minutes to beach, 15 minutes to shopping.

8.0 out of 10, Very good, (13)
"Wonderful location, love the brine scented air & cattails. Perfect location for us to easily visit family. Really enjoyed the relaxing weekend. Will definitely try to stay there again. "
The price is NZ$288
includes taxes & fees
17 July - 18 July
Quiet Bayside cottage. 10 minutes to beach, 15 minutes to shopping.

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

Perfect Family Beach House - Steps from the Beach

10.0 out of 10, Exceptional, (4)
"House was very clean and in a great location. Super close to the beach and a quick walk into town. We enjoyed our stay."
Perfect Family Beach House - Steps from the Beach

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

The price is NZ$303
includes taxes & fees
21 July - 22 July
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

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 NZ$521
includes taxes & fees
16 July - 17 July
Walk to Beach 2BR Near Dining & Shopping

Waterfront & private beach Scandinavian style house near Bellport, NY

9.6 out of 10, Exceptional, (52)
"Beautiful views and a comfortable stay."
Waterfront & private beach Scandinavian style house near Bellport, NY

Private King Bedrm, Pet Pally, Work, Events, LTR, MTR, STR

8.0 out of 10, Very good, (2)
"She was very thorough on the walkthrough and an exceptional host."
The price is NZ$319
includes taxes & fees
22 July - 23 July
Private King Bedrm, Pet Pally, Work, Events, LTR, MTR, STR

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!

Beautiful Waterfront Beach Cottage Sunset Oasis 1hr 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."
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC

Dog-friendly home just blocks from the bay with deck & private hot tub

8.0 out of 10, Very good, (25)
"We had a great stay here! The pictures accurately portrayed the house and there was plenty of space and a really nice outdoor space. There is a wagon at the ferry we weren't made aware of and a lock on the bikes with no code provided. Very much a bare bones house. Kitchen was adequately stocked. The stove only had one working burner. Felt the property was well priced. Would definitely come back!"
Dog-friendly home just blocks from the bay with deck & private hot tub

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (4)
"What a nice place to stay! Key code entry, clean, quiet, comfortable and spacious. This basement apartment exceeded expectations and met all our needs. We would definitely rent this space again."
The price is NZ$327
includes taxes & fees
14 Aug - 15 Aug
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

LUXURY BAY SHORE HOME

2.0 star property
LUXURY BAY SHORE HOME

Tiny Home Private, Students, Nurses, Tech

10.0 out of 10, Exceptional, (1)
"I was very pleased with the property, and the host made me feel more than welcome."
The price is NZ$361
includes taxes & fees
21 July - 22 July
Tiny Home Private, Students, Nurses, Tech

Updated home in great location with spacious living & outdoor features

8.8 out of 10, Excellent, (54)
"Bunk beds, it was very clean and kitchen was great"
Updated home in great location with spacious living & outdoor features

Spacious One Bedroom suite

8.0 out of 10, Very good, (4)
"Nice stay enjoyed it "
Spacious One Bedroom suite
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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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?

Business or Weekend escape: This holiday home rental outside of Head of the Harbor is equipped with a BBQ, 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 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.