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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $538, price is now $321 per person
$321
per person
Nov 18 - Nov 20
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,134, price is now $692 per person
$692
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (JFK)
7/10 Good! (2,403 reviews)
The area is great, but the hotel itself is quite old and outdated. If you’re on a tight budget and need a place to stay, it’ll suffice, but don’t expect anything fancy.

Reviewed on Oct 3, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,122, price is now $689 per person
$689
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
Great location, modern conveniences, and excellent staff

Reviewed on Sep 27, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,615, price is now $1,648 per person
$1,648
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on Sep 28, 2025

Ace Hotel New York

Ace Hotel New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,277, price is now $817 per person
$817
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Burbank (BUR) to New York (JFK)
8/10 Very Good! (1,007 reviews)
Great place to stay, good vibes

Reviewed on Oct 2, 2025

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See all available trips from Columbus to Dering Harbor
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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

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

What to do in Dering Harbor

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

$139
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
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

$148
per adult
Long Island Wine and Food Day Trip with Sommelier host 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 Oct 7 to Oct 8
$91 total
Oct 7 - Oct 8
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"Property was a little dated, but very comfortable. The staff was terrific."

Reviewed on Sep 27, 2025

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (1,012 reviews)
"We have stayed there before so have been pleased with it."

Reviewed on Sep 29, 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$288 nightly
The price is $329 total per night from Nov 2 to Nov 3
$329 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (574 reviews)
"Clean and beautiful view"

Reviewed on Sep 16, 2025

Sound View Greenport
See all 3,961 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.

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.