Holiday Rentals in Head of the Harbor

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Head of the Harbor

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (42)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is €293
includes taxes & fees
5 Dec - 6 Dec
DUNE Fairfield Beach

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is €98
includes taxes & fees
2 Dec - 3 Dec
Business or Weekend escape

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach

The President Mansion Luxurious 7BR Family Retreat

9.6 out of 10, Exceptional, (4)
"I booked this property for my in-laws to stay at for the weekend of my wedding. There was plenty of space for all the adults and the kids to stay comfortably. The host was helpful, attentive, and accommodating. I would happily stay here again in the future. "
The President Mansion Luxurious 7BR Family Retreat

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

7.6 out of 10, Good, (9)
"It was as cute as it looked on-line and gave us a great space for hanging out and enjoying each other's company. That said, I would recommend that you rent this with loved ones as privacy is limited because of the indoor design. With no insulation or dry wall every noise is heard throughout the house! Other nice surprises: new AC units (very quiet), very comfortable beds, and an outdoor shower with good light. The street is very quiet. I was surprised that basic kitchen supplies weren't included...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

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

8.0 out of 10, Very good, (23)
"We loved the location, but the home was loaded with spiders, most appliances did not work (dishwasher did not work, blender, toaster oven, the stove top only half worked) - plus the pots were scratched (and with Teflon not useable) The shower door was broken and would not close, the toilet paper roll holder had no dowel to hold roll, toilet seat very loose, door frames were chipped and dirty, hold in wall next the bed in room with bunkbeds, laundry closet had missing doors. "
Dog-friendly home just blocks from the bay with deck & private hot tub

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

9.4 out of 10, Exceptional, (19)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
The price is €146
includes taxes & fees
9 Dec - 10 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

1 bedroom 1 bath private entrance

9.0 out of 10, Wonderful, (16)
"Place was very clean and well maintained. Host was extremely helpful and communicative! 10/10 would recommend "
The price is €194
includes taxes & fees
30 Nov - 1 Dec
1 bedroom 1 bath private entrance

Beach Apt. Wineries, Shopping, Dining

5.2 out of 10, (7)
"The property manager ensured that booking and check in went smoothly. If you're looking for a 5 star resort or party house, this is NOT the location for you. However, if you're looking for a peaceful getaway on the north shore of Long Island, within walking distance to the beach with your small family, including pet, check it out. Is it flawless? well, no. But you'll find flaws where you look for them. The better question in my mind would be "would I opt to stay there again?".. and the answer is...
The price is €263
includes taxes & fees
3 Dec - 4 Dec
Beach Apt. Wineries, Shopping, Dining

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.8 out of 10, Excellent, (9)
"Clean, spacious home with an amazing pool in a quiet neighborhood. If you're looking for a quiet getaway a good choice!"
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome

6.2 out of 10, (14)
"We all had an amazing time. Convenience to the beach was a bonus. Spectacular views of the ocean n the bay. Plenty of space , screen doors were annoying ( but I also live on the beach and understand how beat up everything gets). Would definitely rent this house again."
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome

Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

9.2 out of 10, Wonderful, (20)
"Stayed here for a girls trip. We were a group of 11. Most of the beds are doubles so probably can’t actually sleep 12 unless you’re a kid or on the smaller side. The way the beds are arranged requires one person to crawl over the other to get out of bed since they’re pushed up against the wall. (Not a dealbreaker but something to consider for guest comfort). As others have mentioned, feels bigger than it looks in the photos. The bathrooms were ok. To break it down: there’s 1 half bath...
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

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

8.8 out of 10, Excellent, (26)
"This property is steps away from the ferry, steps away from the beach and steps away from food, drinks and music. We had a great time. Cassie greeted us and made sure we had everything we needed!!!! She also went out of her way to make my daughters 21st birthday special. Highly recommend this property."
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

Private 1 bedroom apt in a quiet neighborhood, close to all!

9.6 out of 10, Exceptional, (20)
"This apartment was perfect for me. I was in town for a Stony Brook parents weekend and was in close proximity to everything I needed. Comfy bed, very clean, private, and I liked having my coffee out on my patio in the mornings. Great communication from the owner as well. A+ all around!"
The price is €234
includes taxes & fees
30 Nov - 1 Dec
Private 1 bedroom apt in a quiet neighborhood, close to all!

Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

10.0 out of 10, Exceptional, (73)
"Joe was an amazing and kind host. The house has the most unbelievably scenic backyard, with just incredible natural wild life. Was out of a movie. The house if very well equipped for everything you need and is in an amazing location - walk to beach or to town. Really, really an amazing stay. "
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

9.8 out of 10, Exceptional, (64)
"The house was exactly as advertised, the water views were beautiful! Easy access to the North Fork of Long Island."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (25)
"The house was clean, and very comfortable. They are well stocked, even with our odd allergies, we were able to find some snacks. It saved us a good amount of town since it was a short visit. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is €412
includes taxes & fees
3 Dec - 4 Dec
Captain's Cottage - Cold Spring Harbor Water Views

Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!

10.0 out of 10, Exceptional, (43)
"The place was great! The host though of everything, literally. Things that you wouldn't think would even be needed were there. Everything was excellent, cozy and very welcoming. The property was exactly as discribed. I can't say enough about the cleanliness and cozy vibe. We look forward to staying again if we are ever in the area. Ewarm and welcoming. "
Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!
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.
Don't see what you're looking for?
See all available properties in Head of the Harbor
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Head of the Harbor you may be interested in

Hyatt Regency Long Island

3.5 star property
8.0 out of 10, Very good, (1133)
"Great"
The price is €156
includes taxes & fees
1 Dec - 2 Dec
Hyatt Regency Long Island

The Circle Hotel Fairfield

3.0 star property
8.8 out of 10, Excellent, (1307)
"Love this hotel"
The price is €144
includes taxes & fees
4 Dec - 5 Dec
The Circle Hotel Fairfield

Radisson Hotel Hauppauge-Long Island

3.5 star property
6.0 out of 10, (1126)
"There are some good places to eat, but you have to either walk around, or take an Uber to get there. There is an Applebee's & a gas station near by, for your convenience."
The price is €130
includes taxes & fees
11 Dec - 12 Dec
Radisson Hotel Hauppauge-Long Island
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.

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 a Smart TV 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 Town of Brookhaven Wildlife and Ecology Center, 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.