Search Holiday Rentals in Head of the Harbor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
19 Jul - 20 Jul
Tomorrow
20 Jul - 21 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Top Holiday Rentals in Head of the Harbor

DUNE Fairfield Beach
Enjoy a serene beach experience with a tranquil atmosphere, perfect for relaxation or contemplation.

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (60)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach
LUXURY BAY SHORE HOME
Modern kitchen with a central island, stainless steel appliances, and white marble tiles.

LUXURY BAY SHORE HOME

2.0 star property
LUXURY BAY SHORE HOME
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Head of the Harbor Hotel Reviews

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

10/10 Excellent
"yes my stay was pleasant,the room was clean,and quite and my service was great"
ava 1-night trip
Posted 1 day ago
Jake's 58 Casino Hotel - Adult Only

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 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.