Cutchogue Holidays from AU$3,094

Book a Hotel + Flight or Car together to unlock savings

Photo by Adriana T

Your Cutchogue Holiday

Say goodbye to planning worries and hello to a Cutchogue holiday package. With your travel details organised before you take off, you can focus on discovering the best of this city, starting with Village of Southampton, which is great for history, coastal beaches and culture. You'll want to do some exploring during your trip to Cutchogue. Drop by major attractions such as Macari Vineyards, Harbes Family Farm and Pindar Vineyards. Don't put off exploring this city any longer. Your ultimate Cutchogue holiday is a couple of clicks away with Expedia.

The Latest Cutchogue Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
7.6/10 Good! (852 reviews)
Their phone hasn't worked so I couldn't call down to the desk. Also they claimed that they never received payment from Expedia so everyone who registered that way had to give them a credit card again even if we paid in full already. I got the payment taken off, but not sure if they were trying to scam us

Reviewed on 11 Aug. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
What a find! We loved this little hotel in the heart of Little Italy. Great welcoming staff. Wonderful room with a TERRACE! There are tons of restaurants and stores within walking distance. We were thrilled by this place. The bed offered multiple pillow options and was comfortable. We spent quality time on our terrace and on the terrific roof deck!

Reviewed on 15 Aug. 2025

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Save 100% on your flight
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
I absolutely loved this hotel. Very clean and nice and accommodating and great staff!

Reviewed on 13 Aug. 2025

The Dominick

The Dominick

5 out of 5
Manhattan
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
Perfect location for the girls trip with my 15year old daughter. Soho shopping was great! The pool was fantastic and the location was less than a block to the subway. We rode the subway all week and never felt unsafe. Excellent hotel, we will be back!

Reviewed on 14 Aug. 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,945 reviews)
We stay at the property every time we’re in nyc - the location is unbeatable and the staff is awesome!

Reviewed on 10 Aug. 2025

Cutchogue Holiday

Cutchogue Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
3,300
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Long Island Aquarium and Exhibition Centre, 67 Steps Beach and Macari Vineyards

Our pick of the best 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
7.2/10 Good! (689 reviews)
"Great staff and great room, but they used too much (or too strong) of a cleaning solution before we arrived."

Reviewed on 12 Aug. 2025

Get rates
Greenview Inn Riverhead
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is AU$584 per night from 9 Sept to 10 Sept
AU$584
9 Sept - 10 Sept
includes taxes & fees
8.4/10 Very Good! (560 reviews)
"Feels like a remote vacation destination just a couple of hours from home. Self-contained property with private beach and pool away from crowds and tourists, but close to town."

Reviewed on 13 Aug. 2025

Sound View Greenport
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$660 per night from 26 Aug to 27 Aug
AU$660
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"I love this property. But, very disappointed in the pool and lack of variety of food"

Reviewed on 9 Aug. 2025

Saybrook Point Resort & Marina
See all 4,269 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

AU$227
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

AU$1,978
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

AU$1,978
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Cutchogue

Frequently asked questions

How much does a Cutchogue holiday package cost?
You can grab a holiday package to this popular destination from AU$3,094 on Expedia. But how much your holiday to Cutchogue costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Cutchogue?
If you're looking to book a cheap Cutchogue holiday package, consider planning a trip in January, February and March. You're likely to find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Cutchogue?
Generally, a handful of days is enough to check out the main attractions during your Cutchogue holiday. However, if you prefer to have time to kick back or take day tours, consider extending your trip.
How to find the best Cutchogue package deals?
Begin your search for a Cutchogue package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Cutchogue package deal straight away, just play around with your dates and search again. Remember 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Cutchogue trip to match your exact needs. 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 holiday package to Cutchogue?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Cutchogue break.
How to plan a trip to Cutchogue?

  1. Choose when to go: Check your diary and pack your bags. Your favourite season and the activities available will also help you decide when to visit Cutchogue.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Cutchogue.
  3. Decide your trip length: Consider how long you want to spend discovering Cutchogue. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodation: Once you've nailed down your travel dates and duration, book the perfect Cutchogue 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.