Cutchogue Vacations from $381

Book a Hotel + Flight or Car together to unlock savings

Photo by Adriana T

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Cutchogue Vacation

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

The Latest Cutchogue vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $728, price is now $381 per person
$381
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $941, price is now $494 per person
$494
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (125 reviews)
Lovely renovation with everything new and fresh. Just a couple of things missing like a bedside clock and a hair dryer, but a quite good accommodation within easy walking distance of town.

Reviewed on Aug 19, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,262, price is now $1,236 per person
$1,236
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Rooms are so nice and spacious. Plenty of room to enjoy indoor time. Lots of outdoor options on and near the property. Highly recommend. Beautiful views of the bridges and the city.

Reviewed on Aug 19, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,358, price is now $752 per person
$752
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (548 reviews)
Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound

Reviewed on Aug 18, 2025

Windrose On Hudson

Windrose On Hudson

2 out of 5
Save 100% on your flight
Price was $950, price is now $536 per person
$536
per person
Oct 28 - Nov 1
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (8 reviews)
Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again.

Reviewed on Aug 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to Cutchogue
View all trips

Discover the most popular places to visit in Cutchogue

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

Peconic Bay Winery

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

Peconic Bay Winery

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

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

$148
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

$1,299
per traveler
Hamptons Private Day Trip from New York City
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

$559
per adult
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
See all activities in Cutchogue

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
$109 nightly
The price is $125 total per night from Sep 18 to Sep 19
$125 total
Sep 18 - Sep 19
Total includes taxes and fees
7.2/10 Good! (697 reviews)
"All good"

Reviewed on Aug 17, 2025

Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
$201 nightly
The price is $230 total per night from Sep 8 to Sep 9
$230 total
Sep 8 - Sep 9
Total includes taxes and fees
7/10 Good! (913 reviews)
"Nice place. Recommend."

Reviewed on Aug 18, 2025

The Atlantic Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$332 nightly
The price is $380 total per night from Sep 9 to Sep 10
$380 total
Sep 9 - Sep 10
Total includes taxes and fees
8.4/10 Very Good! (561 reviews)
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"

Reviewed on Aug 18, 2025

Sound View Greenport
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cutchogue vacation package cost?
You can grab a vacation package to this popular destination from $381 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?
You can usually find lower rates and better availability in January, October and December. Take a look at our cheap Cutchogue vacation packages and you could get some excellent off-season deals.
How many days is enough for Cutchogue?
The ideal length for your Cutchogue vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to check out all the major attractions and explore some hidden spots along the way.
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 your dates: What you'd like to do in Cutchogue and your favorite season will help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Cutchogue.
  3. Use Expedia's trip planning tool to discover Cutchogue: Research every aspect of your trip to Cutchogue with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the attractions you want to experience in Cutchogue. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your airfare and accommodations: After you've settled on your travel dates and duration, book the perfect Cutchogue vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Cutchogue's best offerings. Find all the incredible things to do in Cutchogue with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Cutchogue vacation packages?
Jet off on your perfect escape to Cutchogue with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next paycheck — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.