Cutchogue Vacation Packages

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Your Cutchogue Vacation

With plenty of highlights as well as some hidden gems, this city is best explored with a Cutchogue vacation package. Find a place to stay in Village of Southampton, which is good for history, coastal beaches and culture. If taking in sights is part of the plan during your trip to Cutchogue, swing by leading attractions like Macari Vineyards, Raphael Winery and Pindar Vineyards. That dream Cutchogue vacation is just a few clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored just for you.

Top Cutchogue Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 19
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (474 reviews)
This hotel is a pure gem. The service is fantastic, the front desk team works to make sure you are truly taken care of, including our dog. Very calm vibe, its super clean, quiet and perfect. Already looking at another couple of nights in August!

Reviewed on Jul. 11, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (531 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on Jul. 12, 2025

ModernHaus SoHo

ModernHaus SoHo

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
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Reviewed on Jul. 2, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 3 - Oct 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7/10 Good! (2,169 reviews)
Clean, friendly, easy check in

Reviewed on Jul. 13, 2025

Ready to book your vacation to Cutchogue?

 

Choose your dates

Cutchogue 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
The price is CA $109 per night from Aug 12 to Aug 13
CA $109
CA $126 total
Aug 12 - Aug 13
includes taxes & fees
7.6/10 Good! (989 reviews)
"The roadside in exceeded my expectations in all areas"

Reviewed on Jul. 9, 2025

Pier Blue Inn Old Saybrook - Essex
Greenview Inn Riverhead
Greenview Inn Riverhead
2 out of 5
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 14 to Jul 15
CA $175
CA $200 total
Jul 14 - Jul 15
includes taxes & fees
7/10 Good! (626 reviews)
"Front desk very nice, although the place is still under construction, room was very comfortable"

Reviewed on Jul. 12, 2025

Greenview Inn Riverhead
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 CA $492 per night from Jul 14 to Jul 15
CA $492
CA $593 total
Jul 14 - Jul 15
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"Fantastic!! Loved staying at this luxurious hotel"

Reviewed on Jul. 8, 2025

Saybrook Point Resort & Marina
See all 4,381 properties in Cutchogue
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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Cutchogue

Bedell Cellars

You can enjoy a tasting or tour at Bedell Cellars during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches.

Bedell Cellars

What to do in Cutchogue

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

CA $218
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
East Hampton Shops

Hamptons Private Day Trip from New York City

CA $1,778
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,774
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Cutchogue

Frequently asked questions

How much does a Cutchogue vacation package cost?
Offering great value package deals from CA $769 on Expedia, you'll be pleasantly surprised at how much a vacation to Cutchogue costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Cutchogue?
If you'd like to book a cheap Cutchogue vacation package, consider travelling in January, February and March. You'll generally find better rates on airfares and hotels during these months --- ideal for travellers wishing to save money.
How many days is enough for Cutchogue?
Typically, a handful of days is enough to explore the major sights during your Cutchogue vacation. However, if you prefer to have some time to chill out or go on day trips, consider extending your itinerary.
How to find the best Cutchogue package deals?
Begin your search for a Cutchogue package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Cutchogue package deal straight away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cutchogue adventure off to a flying start.
Is it cheaper to book a Cutchogue vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can tailor your Cutchogue trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Cutchogue?
If you've got your Cutchogue travel dates locked in, book early to score some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Cutchogue?

  1. Choose your travel dates: What you want to do in Cutchogue and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your accommodations will likely be the largest expense during your trip to Cutchogue.
  3. Decide how long to go away for: Now that you're more familiar with Cutchogue, you can work out the ideal length of your break. Put together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Cutchogue vacation package that brings all your bookings together.

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