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 Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.

Reviewed on Aug. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,736, price is now CA $2,074 per person
CA $2,074
per person
Oct 28 - Oct 31
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Luxury Collection Hotel Manhattan Midtown

The Luxury Collection Hotel Manhattan Midtown

5 out of 5
Manhattan
Price was CA $1,798, price is now CA $1,101 per person
CA $1,101
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Great location, complimentary water which saved us a lot of money on bottled water! Front desk hooked us up with an upgrade. We requested to have all snacks and drinks removed from our son's room and they didn't do it. He got into the snacks and we were charged $160 super annoying, we knew he would get into the snacks and would have appreciated them doing us a solid by removing the $20 gummy bears

Reviewed on Aug. 17, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $2,990, price is now CA $1,871 per person
CA $1,871
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (129 reviews)
Love the hotel especially the design and decor. Staff is so nice and professional. Room service food is excellent. The only negative is the lack of an in-house gym. Would stay again.

Reviewed on Aug. 22, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,352, price is now CA $855 per person
CA $855
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
This hotel had a beautiful view of the Hudson and the city. It was super convenient to the PATH station and parking garage.

Reviewed on Aug. 25, 2025

Ready to book your vacation to Cutchogue?

 

Choose your dates

Cutchogue Hotel Deals

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 $138 per night from Sep 2 to Sep 3
CA $138
CA $158 total
Sep 2 - Sep 3
includes taxes & fees
Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $222 per night from Sep 21 to Sep 22
CA $222
CA $288 total
Sep 21 - Sep 22
includes taxes & fees
The Atlantic Hotel
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 $491 per night from Sep 8 to Sep 9
CA $491
CA $593 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"Very nice checkin"

Reviewed on Aug. 23, 2025

Saybrook Point Resort & Marina
See all 4,273 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

East Hampton Shops

Hamptons Private Day Trip from New York City

CA $1,788
per traveller
Hamptons Private Day Trip from New York City
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $191
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,788
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 $697 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.