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.
Sound View Greenport

Sound View Greenport

4 out of 5
per person
Sep 21 - Sep 24
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very Good! (544 reviews)
Property, views, and interior design is beautiful. Staff was underwhelming. Front desk woman seemed like didnt want to be there. They have a beautiful lobby area with stunning views and a little cafe but you cant enjoy coffee or anything before 5pm which was odd and a waste of a beautiful space. So if its cloudy/cool and you want to sit and enjoy views with a coffee you cant. Bizarre. Also no room service. For the money the amenities were underwhelming.

Reviewed on Aug. 6, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,511 reviews)
We loved the location. What we didn’t like was that there was no refrigerator or microwave in the room. There was also a fight in the room next door to ours and no one checked in to see if we were okay.

Reviewed on Aug. 5, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (2,066 reviews)
Great location and nice on site areas

Reviewed on Aug. 5, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,259 reviews)
Amazing stay! Room was spotless and had everything I needed. I even forgot my phone adapter and reception was kind enough to lend me one. I would definitely recommend NobleDEN

Reviewed on Aug. 5, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on Aug. 6, 2025

Ready to book your vacation to Dering Harbor?

 

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Dering Harbor Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is CA $435 per night from Sep 1 to Sep 2
CA $435
CA $565 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (548 reviews)
"Great location"

Reviewed on Aug. 2, 2025

Sound View Greenport
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 Aug 26 to Aug 27
CA $495
CA $596 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
Beautiful hotel but filled with non hotel guests.
"The hotel was beautiful, on the marina. Our room was nicely decorated and everything was clean - view was amazing. The pool, sauna, etc. was overflowing with people who had "memberships" and not guests of the hotel. I would have appreciated more space for paying guests. Upon checking out, the front ..."

Reviewed on Aug. 4, 2025

Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $346 per night from Aug 17 to Aug 18
CA $346
CA $430 total
Aug 17 - Aug 18
includes taxes & fees
7/10 Good! (892 reviews)
"Great Budget friendly hotel without sacrificing on amenities and comfort would definitely go back again no problem"

Reviewed on Aug. 4, 2025

The Atlantic Hotel
See all 3,992 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.
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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 $203
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 $190
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 $732 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.