Cutchogue Holidays

Photo by Adriana T

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Top hotels in Cutchogue

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 S$118 per night from 3 Aug to 4 Aug
S$118
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"The property was clean."

Reviewed on 26 Jul, 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
7/10 Good! (659 reviews)
"Nice and clean."

Reviewed on 28 Jul, 2025

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Greenview Inn Riverhead
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is S$750 per night from 21 Aug to 22 Aug
S$750
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (544 reviews)
"Every room comes with an ocean view, steps down to the beach. Activities at night. Band at the ocean on certain nights. Will be back every year! Help with bags and getting to room by golf cart."

Reviewed on 22 Jul, 2025

Sound View Greenport
See all 4,307 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.

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

S$204
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

S$1,663
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

S$1,663
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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.