Dering Harbor Vacation Packages

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Your Dering Harbor Vacation

Say goodbye to the stress of planning and hello to a Dering Harbor vacation package. With the finer details organized before you leave, you can focus on discovering this city, starting with Orient Point, which is good for views, fishing and nature. Love to explore? 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery are some of the top-rated places to visit during your trip to Dering Harbor. Don't put off your visit to this destination any longer. Your dream Dering Harbor vacation is a few clicks away with Expedia.

Top Dering Harbor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,914, price is now CA $3,152 per person
CA $3,152
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

Staypineapple, An Artful Hotel, Midtown

Staypineapple, An Artful Hotel, Midtown

3 out of 5
Manhattan
Price was CA $3,342, price is now CA $2,085 per person
CA $2,085
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,037 reviews)
very friendly staff, water refill, good location although the particular street is not so nice,

Reviewed on Aug. 20, 2025

YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Manhattan
Price was CA $2,897, price is now CA $1,870 per person
CA $1,870
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (2,308 reviews)
Good hotel, good price/quality

Reviewed on Aug. 21, 2025

New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,284, price is now CA $834 per person
CA $834
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,915 reviews)
The only problem I had with this hotel was that at check-in, a black woman, a bit rude because I didn't want to pay for the upgrade she was offering, assigned me a room (1460) with a view that was worse than terrible. I immediately went down to the front desk to complain, and a very kind gentleman assisted me. He understood the situation and moved me to an excellent room (3509) with a partial view of Times Square.

Reviewed on Aug. 20, 2025

Ready to book your vacation to Dering Harbor?

 

Choose your dates

Dering Harbor Hotel Deals

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $223 per night from Sep 21 to Sep 22
CA $223
CA $290 total
Sep 21 - Sep 22
includes taxes & fees
7/10 Good! (913 reviews)
"Nice place. Recommend."

Reviewed on Aug. 18, 2025

The Atlantic Hotel
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is CA $495 per night from Sep 8 to Sep 9
CA $495
CA $596 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"The venue is great."

Reviewed on Aug. 20, 2025

Saybrook Point Resort & Marina
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is CA $402 per night from Sep 9 to Sep 10
CA $402
CA $527 total
Sep 9 - Sep 10
includes taxes & fees
8.4/10 Very Good! (561 reviews)
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"

Reviewed on Aug. 18, 2025

Sound View Greenport
See all 3,977 properties in Dering Harbor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Discover the most popular places to visit in Dering Harbor

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

What to do in Dering Harbor

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

CA $204
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $191
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Dering Harbor

Frequently asked questions

How much does a Dering Harbour vacation package cost?
Offering great value package deals from CA $560 on Expedia, you'll be thrilled with how little a vacation to Dering Harbour costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Dering Harbour?
January, February and March are the best times to look for cheap Dering Harbour vacation packages. Opting to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Dering Harbour?
With about 2 days, you'll have enough time to visit popular neighbourhoods like Silver Beach and Hay Beach during your Dering Harbour vacation. Remember to also add Wades Beach and Menhadden Lane Beach to your must-do list. Looking for more adventures? Consider venturing outside of Dering Harbour on day trips and tours.
How to find the best Dering Harbour package deals?
Start your search for a Dering Harbour package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Dering Harbour package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Dering Harbour adventure off to a flying start.
Is it cheaper to book a Dering Harbour vacation as a package?
You can enjoy significant savings on your next Dering Harbour break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Dering Harbour?
If you're considering an impromptu Dering Harbour trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Dering Harbour?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Dering Harbour.
  2. Set a budget: Factor in expenses such as flights, food and transportation when working out how much to save for your trip to Dering Harbour. Then, select a property that suits your budget, whether that's an economical option or a swankier retreat.
  3. Decide your trip length: Think about how much time you want to spend discovering Dering Harbour. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: Once you've settled on your dates and duration, book the perfect Dering Harbour vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.