Find hotels in Head of the Harbor, NY from ￥14,285

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Compare 1,082 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Head of the Harbor hotels

The Madison Fire Island Pines
Exterior

The Madison Fire Island Pines

3.0 star property
8.8 out of 10, Excellent, (46)
"Great place "
The price is ￥26,235
￥29,973 total
includes taxes & fees
Sep 15 - Sep 16
The Madison Fire Island Pines
The Surfside Hotel
Panoramic Room | Memory foam beds, individually decorated, individually furnished

The Surfside Hotel

2.0 star property
9.4 out of 10, Exceptional, (147)
"Great place to stay"
The price is ￥28,326
￥32,575 total
includes taxes & fees
Oct 1 - Oct 2
The Surfside Hotel
Quality Suites
Gazebo

Quality Suites

2.5 star property
8.0 out of 10, Very Good, (1001)
"Great location, many dining options, nice breakfast included with stay. "
The price is ￥14,285
￥16,428 total
includes taxes & fees
Sep 21 - Sep 22
Quality Suites
Home2 Suites by Hilton Long Island Brookhaven
Terrace/patio

Home2 Suites by Hilton Long Island Brookhaven

3.0 star property
9.2 out of 10, Wonderful, (979)
"I enjoyed my stay "
The price is ￥20,793
￥23,755 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Long Island Brookhaven
Best Western Plus Fairfield Hotel
Lobby

Best Western Plus Fairfield Hotel

2.5 star property
8.0 out of 10, Very Good, (1001)
"Kind staff, rooms were clean."
The price is ￥23,547
￥27,079 total
includes taxes & fees
Sep 4 - Sep 5
Best Western Plus Fairfield Hotel
The Circle Hotel Fairfield
Exterior

The Circle Hotel Fairfield

3.0 star property
9.0 out of 10, Wonderful, (1393)
"Great stay "
The Circle Hotel Fairfield
Residence Inn by Marriott Norwalk
Lobby

Residence Inn by Marriott Norwalk

3.0 star property
8.8 out of 10, Excellent, (329)
"The room was very nice."
The price is ￥30,598
￥35,188 total
includes taxes & fees
Sep 14 - Sep 15
Residence Inn by Marriott Norwalk
Comfort Inn Medford - Long Island
Free buffet breakfast

Comfort Inn Medford - Long Island

2.5 star property
8.4 out of 10, Very Good, (1020)
"Great place to stay!"
The price is ￥18,304
￥20,913 total
includes taxes & fees
Sep 29 - Sep 30
Comfort Inn Medford - Long Island
Inn at Longshore
Outdoor wedding area

Inn at Longshore

2.5 star property
9.2 out of 10, Wonderful, (163)
"Location was beautiful, staff very nice, restaurant food and service was wonderful. "
Inn at Longshore
Whitman Motor Lodge
Exterior

Whitman Motor Lodge

2.0 star property
9.0 out of 10, Wonderful, (1003)
"Excellent property! I really enjoyed my stay."
The price is ￥22,011
￥25,146 total
includes taxes & fees
Sep 7 - Sep 8
Whitman Motor Lodge
Delamar Southport
Exterior

Delamar Southport

4.0 star property
9.4 out of 10, Exceptional, (429)
"Very lovely hotel with great staff and awesome Restaurant!"
The price is ￥46,157
￥55,307 total
includes taxes & fees
Sep 7 - Sep 8
Delamar Southport
Homewood Suites by Hilton Ronkonkoma
Exterior

Homewood Suites by Hilton Ronkonkoma

3.0 star property
9.0 out of 10, Wonderful, (506)
"Place was nice breakfast was great. "
The price is ￥26,374
￥30,132 total
includes taxes & fees
Sep 7 - Sep 8
Homewood Suites by Hilton Ronkonkoma
Holiday Inn Long Island-Islip Arpt East by IHG
Ballroom

Holiday Inn Long Island-Islip Arpt East by IHG

3.0 star property
9.2 out of 10, Wonderful, (782)
"Great location while visiting family. "
The price is ￥17,370
￥19,844 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Long Island-Islip Arpt East by IHG
Hampton Inn Long Island-Brookhaven
Gazebo

Hampton Inn Long Island-Brookhaven

2.5 star property
8.8 out of 10, Excellent, (1200)
"Places a little worn down but it's still a very nice place to stay"
The price is ￥18,640
￥21,295 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn Long Island-Brookhaven
Come As You Are Inn
Terrace/patio

Come As You Are Inn

3.0 star property
10.0 out of 10, Exceptional, (52)
"Owner very hospitable. Property super clean with spacious room. Very convenient location "
The price is ￥26,723
￥30,531 total
includes taxes & fees
Oct 2 - Oct 3
Come As You Are Inn
Residence Inn by Marriott Melville
Bar (on property)

Residence Inn by Marriott Melville

3.0 star property
The price is ￥35,927
￥41,047 total
includes taxes & fees
Sep 9 - Sep 10
Residence Inn by Marriott Melville
Grove Hotel
Gallery Quadruple Room, 2 Queen Beds | Blackout drapes, iron/ironing board, free WiFi, bed sheets

Grove Hotel

3.0 star property
9.4 out of 10, Exceptional, (414)
"Great stay"
Grove Hotel
112 Motel
Front of property

112 Motel

2.0 star property
8.6 out of 10, Excellent, (103)
"Very Clean Motel!!!"
The price is ￥21,797
￥24,903 total
includes taxes & fees
Sep 14 - Sep 15
112 Motel
SureStay Plus by Best Western Woodbury Inn
Exterior

SureStay Plus by Best Western Woodbury Inn

2.5 star property
7.2 out of 10, Good, (1017)
"Very nice place to stay. I liked my stay in and the options you have if you want to go out for a coffee, get breakfast, etc. "
The price is ￥18,414
￥20,555 total
includes taxes & fees
Sep 9 - Sep 10
SureStay Plus by Best Western Woodbury Inn
Clegg's Hotel
Front of property

Clegg's Hotel

3.0 star property
8.0 out of 10, Very Good, (194)
"Excellent service and location! Ocean Beach is a great place to get away for a couple of days!"
The price is ￥35,494
￥42,175 total
includes taxes & fees
Sep 4 - Sep 5
Clegg's Hotel
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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Learn more about Head of the Harbor

Head of the Harbor awaits: its wineries, parks, and more!

See all hotels in Head of the Harbor

Top Head of the Harbor Hotel Reviews

More cheap stays in Head of the Harbor

More cheap stays in Head of the Harbor

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2000 North Ocean Ave., Farmingville, NY
The price is ￥18,640 per night from Sep 10 to Sep 11
￥18,640
￥21,295 total
Sep 10 - Sep 11
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's the best place for a stay in Head of the Harbor?

Jake's 58 Casino Hotel - Adult Only, located 6.5 mi (10.5 km) from the heart of Head of the Harbor, is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport and Hampton Inn Long Island-Brookhaven. See all available top hotels, or vacation rentals in Head of the Harbor.

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. See all vacation rentals in Head of the Harbor.

If I need to cancel my hotel reservation in Head of the Harbor, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Head of the Harbor.

Where can I learn more about changing or cancelling my trip to Head of the Harbor?

For additional details about rescheduling or cancelling your trip to Head of the Harbor, click here.

What is staying in Head of the Harbor like?

Visitors can enjoy all that Head of the Harbor has to offer including the wineries and parks. There are 1097 hotels and other accommodations in the surrounding area. Find out more about Head of the Harbor.

What should I do while I'm visiting Head of the Harbor?

Favorite places to visit include Avalon Park and Preserve, Harmony Vineyards, and Stony Brook Grist Mill. You'll also find Smithaven Mall and Sunken Meadow State Park in the area. Check out what more to see and do in Expedia's Head of the Harbor guide.

What's the weather like in Head of the Harbor?

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.