Hotels in Head of the Harbor

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Check prices for these dates

Tonight
Dec 23 - Dec 24
Tomorrow
Dec 24 - Dec 25
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Head of the Harbor?

Panoramic Room | Memory foam beds, individually decorated, individually furnished
The Surfside Hotel
The Surfside Hotel
2.0 star property
9.4 out of 10, Exceptional, (171)
  • cleanliness
    Revitalize steps from the shore with massages and coastal dining at this beachfront retreat.
The price is $135
$155 total
includes taxes & fees
Dec 29 - Dec 30
The Surfside 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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Top landmarks in Head of the Harbor

Avalon Harbor Aerial view from the hills - Catalina Island, California

Avalon Park and Preserve

Avalon Park and Preserve is 0.5 mi (0.8 km) from central Head of the Harbor, why not stop by during your stay. Want to stretch your legs some more? Head to West Meadow Beach Historic District, located nearby.
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Reflections in stream and flowers in bloom at Stony Brook Grist Mill.; Brewster, Massachusetts.

Stony Brook Grist Mill

You might want to get your camera out and head to Stony Brook Grist Mill— just one of the landmarks located 1 mi (1.5 km) from central Head of the Harbor.
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Learn more about Head of the Harbor

Head of the Harbor is well-known for its attractions such as Avalon Park and Preserve and Stony Brook Grist Mill.

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Avalon Harbor Aerial view from the hills - Catalina Island, California

Check out reviews of Head of the Harbor hotels guests love

SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

10/10 Excellent
"Good location and room. Also, it provided a nice choice of items during breakfast."
Emery 3-night trip
Posted 1 day ago
SureStay Plus by Best Western Woodbury Inn

Frequently asked questions

What accommodations do travelers recommend in Head of the Harbor?
Guests like Hyatt Regency Long Island, Holiday Inn Express Hauppauge-Long Island and La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport.
Can I book refundable accommodations in Head of the Harbor?
If you want the flexibility to change your plans to Head of the Harbor, most hotels provide refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Head of the Harbor be like during my vacation?
The warmest months in Head of the Harbor are usually July and August with an average temp of 72°F. January and February are the chilliest months when the average temp is 37°F. The rainiest months are October and December.
Why should I book my Head of the Harbor hotel with Hotels.com?
There are plenty of reasons to book your Head of the Harbor travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.