Dering Harbor Vacations from $256

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Dering Harbor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $471, price is now $256 per person
$256
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
The staff were friendly and helpful. There was air con but with it being -9 we didn’t use it. The room was well heated though so didn’t notice the cold. The room we had was a bit small for 4 people but we’ve stayed before and had a very spacious room, just depends what’s available in check in. The location is amazing, 3 min walk and your on Times Square!

Reviewed on Dec 12, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,061, price is now $486 per person
$486
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Place was big, clean and well located

Reviewed on Dec 13, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $854, price is now $433 per person
$433
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Electric charging in back

Reviewed on Dec 9, 2025

Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
Price was $1,001, price is now $545 per person
$545
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $1,011, price is now $564 per person
$564
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
helpful staff, nice rooms, location

Reviewed on Nov 24, 2025

Don't see what you're looking for?
See all available trips from Columbus to Dering Harbor
View all trips

Discover the most popular places to visit in Dering Harbor

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve

Shelter Island Historical Society

4/5(1 review)

You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

What to do in Dering Harbor

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Dering Harbor

Dering Harbor Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $91 total per night from Dec 21 to Dec 22
$91 total
Dec 21 - Dec 22
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
The staff couldn’t have been nicer! Courteous and caring. The room was immaculate with all necessary amenities. Somewhat dated but not shabby. Very close to town. Parking was ample and right outside my door! I attended a concert at the Kate and did not want to drive an hour home late that evening, ...

Reviewed on Dec 7, 2025

Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $256 total per night from Jan 1 to Jan 2
$256 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!

Reviewed on Dec 7, 2025

Water's Edge Resort & Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$212 nightly
The price is $242 total per night from Jan 12 to Jan 13
$242 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
8.4/10 Very Good! (598 reviews)
Great room with amazing views! Staff was fantastic and the food was great too

Reviewed on Nov 28, 2025

Sound View Greenport
See all 3,974 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.

Find the Best Dering Harbor Vacation Packages

Dering Harbor Essential Information

Language
English
Currency
U.S dollars
Top Sights
Wades Beach, Shell Beach and Menhadden Lane Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Dering Harbor vacation package cost?
You can grab a vacation package to this popular destination from $256 on Expedia. However, how much your vacation to Dering Harbor costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Dering Harbor?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Dering Harbor vacation packages and you could land some great off-season discounts.
How many days is enough for Dering Harbor?
With a well-organized travel plan, you can easily hit the top Dering Harbor sights in a handful of days. But if you want to explore off the beaten track or go on day trips, think about booking your Dering Harbor vacation for longer.
How to find the best Dering Harbor package deals?
Use Expedia's handy filters to find some unbeatable Dering Harbor package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Dering Harbor package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Dering Harbor vacation as a package?
You can enjoy significant savings on your Dering Harbor getaway by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Dering Harbor?
Score fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Dering Harbor getaway.
How to plan a trip to Dering Harbor?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to Dering Harbor.
  2. Budget wisely: In addition to the cost of your hotel, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may come up during your trip to Dering Harbor.
  3. Use our trip planning tool to discover Dering Harbor: Research every aspect of your trip to Dering Harbor with this comprehensive planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Dering Harbor. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Dering Harbor vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Have a look at our dedicated travel guide to find some incredible things to do in Dering Harbor. Book tickets or make reservations in advance to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Dering Harbor vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Dering Harbor break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.