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Head of the Harbor Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Head of the Harbor holiday rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is RM725
RM1,083 total
includes taxes & fees
12 Oct - 13 Oct
DUNE Fairfield Beach
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

2. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is RM705
RM1,210 total
includes taxes & fees
21 Oct - 22 Oct
Spacious 3BR Family Home Near Everything
A white shelving unit with decorative items, including a mixtape box, two golden bird figurines, and three glass vases.

3. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is RM541
RM1,225 total
includes taxes & fees
12 Oct - 13 Oct
Sundown Escape-South Shore Long Island
Interior

4. Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is RM495
RM1,993 total
includes taxes & fees
28 Oct - 29 Oct
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

5. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is RM2,489
RM3,782 total
includes taxes & fees
11 Oct - 12 Oct
4 Mi to Beach & Dtwn! Charming Fairfield 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.
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Top Head of the Harbor Hotel Reviews

Danfords Hotel and Marina

Danfords Hotel and Marina

8/10 Good
"The location is great, and it's a nice place."
Esther 1-night trip
Posted less than an hour ago
Danfords Hotel and Marina

Find out more about Head of the Harbor

Search for holiday rentals in Head of the Harbor on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Head of the Harbor using one of the methods below:

  • View our selection of featured holiday rentals in Head of the Harbor
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Look no further and take a look at our great range of rental properties in Head of the Harbor!

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 Stony Brook Grist Mill and Harmony Vineyards.

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.