Cutchogue Vacations from $404

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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.
Topping Rose House

Topping Rose House

4.5 out of 5
Price was $800, price is now $404 per person
$404
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $2,369, price is now $1,179 per person
$1,179
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
Pro: Desk staff was very nice and helpful. Con: Cleaning carts being rolled around the floors are super loud

Reviewed on Jan 31, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,453, price is now $787 per person
$787
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
Great hotel, great location, perfect trip.

Reviewed on Jan 31, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $1,065, price is now $581 per person
$581
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Our room was clean, they made our bed every day, staff was nice and polite I had no issues! It was wonderful. Amazing location and I would definitely stay here again

Reviewed on Jan 31, 2026

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Discover the most popular places to visit in Cutchogue

Wine on the vine!

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

8 Hands Farm

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

8 Hands Farm

What to do in Cutchogue

East Hampton Shops

Hamptons Private Day Trip from New York City

$1,299
per traveler
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

$1,299
per traveler
The Hamptons and Long Island Wineries Private Tour
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

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
$79 nightly
The price is $91 total per night from Feb 2 to Feb 3
$91 total
Feb 2 - Feb 3
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!

Reviewed on Jan 23, 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$151 nightly
The price is $173 total per night from Feb 9 to Feb 10
$173 total
Feb 9 - Feb 10
Total with taxes and fees
8.4/10 Very Good! (608 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 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
$244 nightly
The price is $281 total per night from Feb 3 to Feb 4
$281 total
Feb 3 - Feb 4
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Great room and staff

Reviewed on Jan 14, 2026

Water's Edge Resort & Spa
See all 4,285 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.

Find the Best Cutchogue Vacation Packages

Cutchogue Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
3,300
Max Temp Winter
40ºF
Max Temp Summer
75ºF
Top Sights
Coopers Beach, Wolffer Estates Vineyard and The Hamptons Beaches

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Frequently asked questions

How much does a Cutchogue vacation package cost?
You can grab a vacation package to this popular destination from $404 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.

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