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.
Hotel St. James
Manhattan
Price was CA $2,193, price is now CA $1,250 per person
CA $1,250
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
Great hotel, awesome staff. Bilingual staff.
Reviewed on Feb 10, 2026
The Fifth Avenue Hotel
Manhattan
Price was CA $5,205, price is now CA $2,909 per person
CA $2,909
per person
Apr 22 - Apr 28
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping.
Reviewed on Jan 3, 2026
The Towers at Lotte New York Palace
Manhattan
Price was CA $4,432, price is now CA $2,634 per person
CA $2,634
per person
Apr 22 - Apr 28
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (638 reviews)
Close to major shopping and multiple dining options
Reviewed on Jan 21, 2026
The Wall Street Hotel
Manhattan
Price was CA $3,406, price is now CA $2,055 per person
CA $2,055
per person
Apr 22 - Apr 28
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (591 reviews)
Great room, great staff, great bar
Reviewed on Feb 4, 2026
NobleDEN Hotel
Manhattan
Price was CA $2,255, price is now CA $1,374 per person
CA $1,374
per person
Mar 18 - Mar 24
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
NobleDEN has very clean rooms. The staff are also very friendly and accommodating. There are some nice amenities included in your stay including discounts at nearby establishments with your keycard! Cool and unexpected.
Reviewed on Feb 10, 2026
Dering Harbor Hotel Deals
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is CA $189 per night from Feb 24 to Feb 25
CA $189
CA $255 total
Feb 24 - Feb 25
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from Feb 15 to Feb 16
CA $86
CA $99 total
Feb 15 - Feb 16
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Room was clean and warm and the staff was very friendly
Reviewed on Feb 1, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is CA $265 per night from Feb 17 to Feb 18
CA $265
CA $328 total
Feb 17 - Feb 18
includes taxes & fees
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.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
