Cutchogue Holidays from £1,092

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    Save up to £335 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Your Cutchogue Holiday

With plenty of highlights as well as some hidden gems, this city is best explored with a Cutchogue holiday 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 holiday is just a few clicks away. Search accommodation, flights and more on Expedia for an adventure that's tailored just for you.

Top Cutchogue Flight + Hotel 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
Save 100% on your flight
per person
16 Sept - 23 Sept
found 6 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on 6 Aug 2025

La Quinta Inn & Suites by Wyndham Times Square South

La Quinta Inn & Suites by Wyndham Times Square South

3 out of 5
Manhattan
per person
20 Oct - 24 Oct
found 15 hours ago
Return direct flight included
Manchester (MAN) to New York (JFK)
9/10 Wonderful! (1,010 reviews)
Clean. Good location to where I needed to be.

Reviewed on 28 Jul 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
17 Oct - 22 Oct
found 1 day ago
Return direct flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on 3 Aug 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
9 Sept - 13 Sept
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (1,009 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul 2025

ModernHaus SoHo

ModernHaus SoHo

4.5 out of 5
Manhattan
Save 100% on your flight
per person
23 Sept - 30 Sept
found 23 hours ago
Return flight included
London (LGW) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
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Reviewed on 2 Jul 2025

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

Top hotels in Cutchogue

Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
7/10 Good! (668 reviews)
"New clean room"

Reviewed on 2 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 £308 per night from 1 Sept to 2 Sept
£308
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (549 reviews)
"Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread ..."

Reviewed on 5 Aug 2025

Sound View Greenport
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is £326 per night from 26 Aug to 27 Aug
£326
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
Beautiful hotel but filled with non hotel guests.
"The hotel was beautiful, on the marina. Our room was nicely decorated and everything was clean - view was amazing. The pool, sauna, etc. was overflowing with people who had "memberships" and not guests of the hotel. I would have appreciated more space for paying guests. Upon checking out, the front ..."

Reviewed on 4 Aug 2025

Saybrook Point Resort & Marina
See all 4,299 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

8 Hands Farm

Enjoy an outing to 8 Hands Farm during your stay in Cutchogue.

8 Hands Farm

McCall Wines

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

McCall Wines

What to do in Cutchogue

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

£103
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
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

£110
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

£967
per traveller
Hamptons Private Day Trip from New York City
See all activities in Cutchogue

Frequently asked questions

How much does a Cutchogue travel package cost?
We make it easy to see the world, with Cutchogue travel packages starting from just £1,092. You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate getaway, why not add some activities and tours to your itinerary?
If I'm not able to travel, can I cancel my Cutchogue travel package?
Certainly, and we're here to help. You may be able to cancel or change your Cutchogue travel package at no cost within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, take a look at our Customer Service Portal for further information.
How do I get a cheap travel package to Cutchogue?
Bundling your hotel and flight with Expedia won't just save valuable time — it'll save you dollars too. A Cutchogue travel package makes it a cinch to arrange your perfect trip. With more than 550 airlines throughout the world to pick from, finding flights that fit your busy schedule won't be an issue. In addition to that, we have over 1,000,000 hotel options globally to select from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Does Expedia offer Book Now, Pay Later Cutchogue holidays?
Yes. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that suit all budgets, so you can jet away on that well-earned holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip in multiple transactions.
  • Low deposit holidays: Pressing the "book now" button is much easier with this option. Simply put down a small deposit on your booking and then start working on your travel plans.

How far in advance should I book my Cutchogue holiday?
While prices fluctuate, we generally suggest booking your holiday as soon as possible. Most international airfares can be found on Expedia up to 12 months in advance. If circumstances have left you booking late, you might still get lucky. Low prices to Cutchogue sometimes appear only weeks before departure.
What does an Expedia Cutchogue travel package include?
That's up to you. You can select from a range of Cutchogue packages, such as a hotel, rental car and flight. You can also book a hotel and a flight, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your ideal Cutchogue break looks like, get ready to save!
What should I know before booking a Cutchogue travel package?
You'll enjoy excellent savings when you bundle your flights, hotels and rental cars into a travel package. Not only that, booking everything together makes trip planning much easier. So why waste time or money? Whether you're putting together a ritzy city getaway or a budget family adventure, explore our travel packages today.
Can I choose my airline with a Cutchogue Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Just select the airline you want and put together the perfect Cutchogue trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.