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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Head of the Harbor bed & breakfast

Terrace/patio
Come As You Are Inn

Come As You Are Inn

Come As You Are Inn
3.0 star property
Sayville
10.0 out of 10, Exceptional, (58)
"Nice breakfast"
United States
Jose
$213 nightly
The price is $244
Dec 26 - Dec 27
Total with taxes and fees
Come As You Are Inn
Pool
The Jahmtons Guest Room

The Jahmtons Guest Room

The Jahmtons Guest Room
Ridge
8.6 out of 10, Excellent, (31)
"Very cozy room and nice people who owned the house. We only met Wayne but he was very cordial and kind. The dogs were wonderful as well :)"
United States
Michael
$183 nightly
The price is $209
Dec 17 - Dec 18
Total with taxes and fees
The Jahmtons Guest Room
View from property
The Ocean Bay House

The Ocean Bay House

The Ocean Bay House
3.5 star property
Bay Shore
10.0 out of 10, Exceptional, (114)
"What a gem! Great location to Fire Island and restaurants- lovely walk and neighborhood. Going to return next year!!!"
United States
Renee
$340 nightly
The price is $388
Dec 31 - Jan 1, 2026
Total with taxes and fees
The Ocean Bay House
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

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

10/10 Excellent
"Good"
Ikromjon 1-night trip
Posted 16 hours ago
Holiday Inn Express Hauppauge-Long Island

Find out more about Head of the Harbor

Head of the Harbor B&B information

Number of reviews
203
Accommodation
4 B&B
Lowest Price
$209
Highest Price
$388

Frequently asked questions

Searching for B&Bs in Head of the Harbor?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're a solo traveler hoping to make some connections, B&Bs can be a great choice for many travelers. If your ideal vacation to Head of the Harbor includes spending lots of time outside, Avalon Park and Preserve is a good spot to enjoy the scenery.
How do you know if a B&B is the right choice for you?
With attentive service, opportunities to meet other guests, and top-rated breakfasts, B&Bs provide a unique environment.
What are the best B&Bs in Head of the Harbor?
Here are some B&Bs in the area: The Jahmtons Guest Room: 13.5 mi (21.7 km) from the heart of Head of the Harbor.Come As You Are Inn: 3 rooms. 12 mi (19.4 km) from the downtown core. Enjoy the private yard and deli. The Ocean Bay House: 9 rooms. Situated 13.7 mi (22 km) from the heart of Head of the Harbor. Enjoy the designer toiletries and marina onsite. Cozy and Stylish 1 Bedroom Guest Suite: 17.5 mi (28.2 km) from the heart of downtown. Enjoy the sauna and outdoor swimming pool.
What's the best time of year to stay at a B&B in Head of the Harbor?
When you're planning your escape to Head of the Harbor, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Head of the Harbor is 55 inches.
What is there to do in Head of the Harbor?
When you want to explore some things to do in town, Avalon Park and Preserve and Stony Brook Grist Mill are some notable sights to visit. You might check out Harmony Vineyards if you have time to see more of the area.
How can I get to and around Head of the Harbor?
Mapping out your trip in and around Head of the Harbor is easy with these transportation options. Fly into MacArthur Airport (ISP), which is located 8.5 mi (13.7 km) away from the city center. Otherwise, you can search for flights to Shirley, NY (WSH-Brookhaven Calabro), which is 15.9 mi (25.5 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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