Cutchogue Vacations from $268

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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.
NoMo SoHo

NoMo SoHo

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $466, price is now $268 per person
$268
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,224 reviews)
Location was perfect. Rooms were small, walls were paper thin. I could hear clear conversations from the room next to us like they were in our room. Headboard was peeling, definitely can use some renovations. Was not up to my expectations when considering the price.

Reviewed on Nov 4, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $761, price is now $389 per person
$389
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Amazing stay. Great food, great bed, great staff

Reviewed on Nov 5, 2025

The Mansion at Glen Cove

The Mansion at Glen Cove

4 out of 5
Save 100% on your flight
Price was $593, price is now $327 per person
$327
per person
Jan 22 - Jan 25
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7/10 Good! (1,001 reviews)
perfect stay. love the nature and the vibe there. will be best for vacation.

Reviewed on Nov 2, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,563, price is now $868 per person
$868
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Nice hotel , needs a bit of tender love and care !

Reviewed on Oct 14, 2025

NOVA HOTEL BRONX

NOVA HOTEL BRONX

2 out of 5
Save 100% on your flight
Price was $696, price is now $413 per person
$413
per person
Jan 14 - Jan 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.2/10 Very Good! (209 reviews)
Was looking for a convenient, clean and safe hotel on a visit to NYC for the marathon, and I found it! They’ve got free self-parking that’s constantly monitored, and their rooms are clean and tidy. The staff was professional, courteous and happy to help. It’s also about an 18 min walk to the subway/train stations—perfect for travelers! Very pleased and hope to be back!

Reviewed on Nov 5, 2025

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Discover the most popular places to visit in Cutchogue

Bedell Cellars

4/5(2 reviews)

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
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip 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
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
$82 nightly
The price is $95 total per night from Nov 11 to Nov 12
$95 total
Nov 11 - Nov 12
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...

Reviewed on Nov 3, 2025

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$195 nightly
The price is $223 total per night from Nov 20 to Nov 21
$223 total
Nov 20 - Nov 21
Total with taxes and fees
8.4/10 Very Good! (585 reviews)
We love the Sound View. We stay every year for a girls’ weekend. Rooms are great with a beautiful view. One thing the rooms could use are a standing closet for your clothes. Otherwise, it’s lovely.

Reviewed on Nov 2, 2025

Sound View Greenport
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$278 nightly
The price is $320 total per night from Dec 7 to Dec 8
$320 total
Dec 7 - Dec 8
Total with taxes and fees
9.4/10 Exceptional! (1,008 reviews)
This hotel has everything!!! We went for a girls’ night away, and we never had to leave. The heated pools and steam/sauna rooms were wonderful. The on-site restaurants and room service options were delicious. Our room was very clean and cozy, especially with the service of a staff member starting ...

Reviewed on Nov 2, 2025

Saybrook Point Resort & Marina
See all 4,266 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 $268 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.