Cutchogue Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Adriana T

Top hotels in Cutchogue

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 7.603.374 ₫ per night from 9 Sept to 10 Sept
7.603.374 ₫
9.972.116 ₫ total
9 Sept - 10 Sept
includes taxes & fees
8.4/10 Very Good! (557 reviews)
"Thank you Adrian. She was wonderful and made my mother’s birthday special. Every interaction we had with the staff was positive. The halyard served a delicious lobster roll in a beautiful setting. We will be back."

Reviewed on 9 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 9.219.137 ₫ per night from 26 Aug to 27 Aug
9.219.137 ₫
11.126.481 ₫ total
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (1,003 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 4,288 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.

Popular places to visit

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

Pellegrini Vineyards

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

Pellegrini Vineyards

Pugliese Vineyards

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

Pugliese Vineyards

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.