Dering Harbor Holidays from AU$1,150

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Your Dering Harbour Holiday

With plenty of highlights as well as some hidden gems, this city is best explored with a Dering Harbour holiday package. Book a hotel in Orient Point, which is good for views, fishing and nature. A trip to Dering Harbour is a terrific opportunity to do some sightseeing. Be sure to look around renowned attractions like 67 Steps Beach, Kontokosta Winery and Sunset Beach. Expedia is here to help you escape your routine. Tailor your holiday to Dering Harbour to suit your travel style, whatever that may look like.

The Latest Dering Harbor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 20 hours ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (1,487 reviews)
The lobby area was welcoming and decorated nicely. Our room was spacious and had a great private balcony. We enjoyed the breakfast pastry and coffee. The only negative was the amount of time it took to check in when we arrived at a non peak time. We also had a visit from housekeeping an hour before checkout which made us feel rushed to leave. I would recommend this location.

Reviewed on 16 Jul. 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 20 hours ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
7.8/10 Good! (1,475 reviews)
Amazing landscaping and great views. Property was in a great location along with great customer service and staff

Reviewed on 17 Jul. 2025

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 20 hours ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
8.2/10 Very Good! (1,310 reviews)
Great attention. Allowed late check out

Reviewed on 18 Jul. 2025

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
per person
2 Sept - 7 Sept
found 20 hours ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
9.4/10 Exceptional! (1,226 reviews)
Excellent location to attend concert at the Beacon and to explore the Upper Westside.

Reviewed on 18 Jul. 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Hamilton (YHM) to New York (JFK)
7.8/10 Good! (2,087 reviews)
I had a fantastic experience here. The rooms are spacious and modern, and the location is perfect for exploring Manhattan. I asked for more toiletries, and they provided everything I needed promptly. Amazing service!

Reviewed on 14 Jul. 2025

Dering Harbor Holiday

Dering Harbour Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Shell Beach, Menhadden Lane Beach and Wades Beach

Our pick of the best Dering Harbor Hotel Deals

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
The price is AU$195 per night from 3 Aug to 4 Aug
AU$195
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (1,013 reviews)
Swimming pool is the best
"The pool was the best part of the hotel. Warm and deep enough, long enough to actually swim some 1/2 laps"

Reviewed on 14 Jul. 2025

Quality Inn Old Saybrook - Westbrook
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
The price is AU$141 per night from 21 July to 22 July
AU$141
21 July - 22 July
includes taxes & fees
7.6/10 Good! (998 reviews)
"Very convenient to the beaches and very clean room. I had some trouble with the door lock but nothing major. I'm a doofus. Will definitely return."

Reviewed on 16 Jul. 2025

Pier Blue Inn Old Saybrook - Essex
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$666 per night from 20 July to 21 July
AU$666
20 July - 21 July
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"loved being able to order food around the pool"

Reviewed on 16 Jul. 2025

Saybrook Point Resort & Marina
See all 4,073 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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

Wades Beach

Why not spend a care-free 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

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

AU$243
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

AU$210
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 holiday package cost?
You can grab a holiday package to this popular destination from AU$1,150 on Expedia. However, how much your holiday to Dering Harbour costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Dering Harbour?
January, February and March are great times to look for cheap Dering Harbour holiday packages. Travelling in less busy periods means you can generally find better prices on flights and hotels.
How many days is enough for Dering Harbour?
With a well-planned schedule, you can easily tick off the main Dering Harbour sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Dering Harbour holiday for longer.
How to find the best Dering Harbour package deals?
Use Expedia's handy filters to find some unbeatable Dering Harbour 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 Harbour 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 holiday package as soon as possible.
Is it cheaper to book a Dering Harbour holiday as a package?
You can enjoy significant savings on your Dering Harbour getaway by booking a tailored holiday 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 holiday package to Dering Harbour?
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 Harbour getaway.
How to plan a trip to Dering Harbour?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Dering Harbour.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to experiences and flights. Your hotel will likely be the largest expense during your trip to Dering Harbour.
  3. Decide your trip length: Think about how much time you want to spend exploring Dering Harbour. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Dering Harbour holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.