Dering Harbor Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Dering Harbor

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 S$162 per night from 5 Aug to 6 Aug
S$162
5 Aug - 6 Aug
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Just a little tired looking, but very nice staff. Everything went well. Thank you. Good value for everything."

Reviewed on 21 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 S$118 per night from 5 Aug to 6 Aug
S$118
5 Aug - 6 Aug
includes taxes & fees
7.6/10 Good! (1,001 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
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is S$741 per night from 21 Aug to 22 Aug
S$741
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (541 reviews)
"Every room comes with an ocean view, steps down to the beach. Activities at night. Band at the ocean on certain nights. Will be back every year! Help with bags and getting to room by golf cart."

Reviewed on 22 Jul, 2025

Sound View Greenport
See all 4,019 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.

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

S$204
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

S$175
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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.