Cutchogue Vacations from ￥386,279

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The Latest Cutchogue Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Price was ￥519,878, price is now ￥386,279 per person
￥386,279
per person
Sep 14 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
7.6/10 Good! (6,916 reviews)
Clean room, helpful staff, great location, quiet and friendly area

Reviewed on Jul 12, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥588,421, price is now ￥391,790 per person
￥391,790
per person
Sep 3 - Sep 9
found 12 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Great

Reviewed on Jul 12, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥714,840, price is now ￥477,590 per person
￥477,590
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Excellent experience at the RIU Manhattan Times Square Hotel. The professionalism started the moment we walked into the hotel until we checked out 5 days later. Extremely clean room, comfortable beds and roomy (for a NY hotel where space is gold). Thank you to the entire RIU staff for making us feel comfortable in our home away from home for a week!

Reviewed on Jul 12, 2026

Washington Square Hotel

Washington Square Hotel

3.5 out of 5
Manhattan
Price was ￥606,798, price is now ￥430,190 per person
￥430,190
per person
Sep 14 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (1,303 reviews)
Gym is closed but otherwise great. Awesome location!

Reviewed on Jul 12, 2026

Hotel Park Ave NYC

Hotel Park Ave NYC

4.5 out of 5
Manhattan
Price was ￥591,216, price is now ￥427,369 per person
￥427,369
per person
Sep 14 - Sep 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,408 reviews)
I will be back! I found my NYC home whenever I visit.

Reviewed on Jul 12, 2026

Find the Best Cutchogue Vacation Packages

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 refundable
The price is ￥14,132 per night from Jul 22 to Jul 23
￥14,132
￥16,252 total
Jul 22 - Jul 23
includes taxes & fees
8/10 Very Good! (1,016 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on Jul 11, 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ￥77,052 per night from Aug 3 to Aug 4
￥77,052
￥101,886 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ￥48,342 per night from Aug 12 to Aug 13
￥48,342
￥58,382 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"your unit bathrooms need an upgrade. it would be inexpensive to use a piece of furniture at the sinks. the furniture in the italian restaurant could also be better."

Reviewed on Jul 11, 2026

Water's Edge Resort & Spa
See all 4,300 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.

Stay near popular Cutchogue attractions

Bedell Cellars

8.6/10 (4 reviews)
This award-winning Long Island winery served its 2009 Merlot at the 2013 Presidential Inauguration. Sample handcrafted wines in a renovated barn with panoramic vineyard views and artisanal cheese pairings.
See properties

What to do in Cutchogue

great fun with friends

Full Day Private Long Island Wine Tours from New York City

￥30,720
per adult
Full Day Private Long Island Wine Tours from New York City
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

￥211,139
per traveler
100% of travellers recommend
Hamptons Private Day Trip from New York City
The Hamptons Coastal Escape from NYC

The Hamptons Coastal Escape from NYC

￥149,260
per traveler
The Hamptons Coastal Escape from NYC
See all activities in Cutchogue

Frequently asked questions

How much does a Cutchogue vacation package cost?
You can grab a vacation package to this popular destination from ￥386,279 on Expedia. But how much your vacation 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 vacation 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 vacation. 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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize 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 vacation 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 favorite 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 accommodations 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 accommodations: Once you've nailed down your travel dates and duration, book the perfect Cutchogue vacation package for you.

Explore a world of travel with Expedia

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