Dering Harbor Trips (flight + hotel)

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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 P6,251 per night from Aug 3 to Aug 4
P6,251
P7,188 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,004 reviews)
"The staff was exceptionally helpful in orienting us to the hotel and helping us find a restaurant that met our needs."

Reviewed on Jul 7, 2025

Quality Inn Old Saybrook - Westbrook
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 P19,885 per night from Jul 20 to Jul 21
P19,885
P23,999 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Fantastic!! Loved staying at this luxurious hotel"

Reviewed on Jul 8, 2025

Saybrook Point Resort & Marina
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 P4,413 per night from Jul 16 to Jul 17
P4,413
P5,075 total
Jul 16 - Jul 17
includes taxes & fees
7.6/10 Good! (988 reviews)
"Friendly staff and met needs of offering cold water upon check in and extra pillows when requested. The bed was comfortable and hotel was quiet at night even though sold out for a busy holiday weekend. The room and bathroom was clean but does need some modernization."

Reviewed on Jul 8, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,042 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.

Popular places to visit

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

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

P8,964
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Vetted Flights and food pairings at local winery.

Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM

P19,112
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

P7,946
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 Harbor vacation package cost?
You can grab a vacation package to this popular destination 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?
January, February and March are great times to look for cheap Dering Harbor vacation packages. Traveling in less busy periods means you can generally find better prices on flights and hotels.
How many days is enough for Dering Harbor?
With a well-planned schedule, you can easily tick off the main Dering Harbor sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider 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. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Dering Harbor.
  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 Harbor.
  3. Decide your trip length: Think about how much time you want to spend exploring Dering Harbor. 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 accommodations: After you've nailed down your dates and duration, lock in the right Dering Harbor vacation package for you.

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