Dering Harbor Vacations from $321

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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.

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 $567, price is now $321 per person
$321
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
The room was simple but clean and the location couldn’t be beat!

Reviewed on Feb 11, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,748, price is now $904 per person
$904
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $610, price is now $327 per person
$327
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Rooms Property were Fantastic !

Reviewed on Feb 6, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $649, price is now $360 per person
$360
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Yes amazing will recommend and do it all over again

Reviewed on Feb 11, 2026

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Discover the most popular places to visit in Dering Harbor

Man watching sailboat on Long Island Sound

Wades Beach

Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach
Colorful pebbles and shells on a beach

Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach

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

Dering Harbor Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$158 nightly
The price is $180 total per night from Feb 26 to Feb 27
$180 total
Feb 26 - Feb 27
Total with taxes and fees
8.4/10 Very Good! (609 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

Sound View Greenport
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 Feb 15 to Feb 16
$91 total
Feb 15 - Feb 16
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
Room was clean and warm and the staff was very friendly

Reviewed on Feb 1, 2026

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
$244 nightly
The price is $281 total per night from Feb 16 to Feb 17
$281 total
Feb 16 - Feb 17
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Great room and staff

Reviewed on Jan 14, 2026

Water's Edge Resort & Spa
See all 3,983 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

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Frequently asked questions

How much does a Dering Harbor vacation package cost?
You can grab a vacation package to this popular destination from $321 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.