Cutchogue Vacations from $897

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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.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (533 reviews)
Our stay was wonderful

Reviewed on Sep 21, 2024

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,800 reviews)
Great location and nicely appointed rioms and hotel.

Reviewed on Sep 20, 2024

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
Dec 5 - Dec 8
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (2,127 reviews)
bath towels are not clear, they have weak smell

Reviewed on Sep 22, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,106 reviews)
Need desperately a full renovation

Reviewed on Sep 12, 2024

Life Hotel New York

Life Hotel New York

3.5 out of 5
Manhattan
Save 100% on your flight
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,010 reviews)
Perfect location for a NYC adventure. Staff was fantastic! They went above and beyond in many areas. Would definitely recommend this area. Perfect walking distance to all areas of NYC and very clean area!

Reviewed on Sep 16, 2024

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

Ready to book your vacation to Cutchogue?

 

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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
The price is $82 per night from Sep 25 to Sep 26
$82
includes taxes & fees
$71 per night
Sep 25 - Sep 26
7.6/10 Good! (852 reviews)
"Nice and quite…cozy and warm decorated"

Reviewed on Sep 19, 2024

Pier Blue Inn Old Saybrook - Essex
Greenview Inn Riverhead
Greenview Inn Riverhead
2 out of 5
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is $101 per night from Oct 1 to Oct 2
$101
includes taxes & fees
$88 per night
Oct 1 - Oct 2
6.4/10 (495 reviews)
"Recently renovated rooms are simple but functional and clean. The noise insulation between rooms even in the renovated area is minimal, so we did hear the guests in the next room over. The hotel is near a race track, so there was a lot of noise from the zooming racecars too. Overall it was a good ..."

Reviewed on Sep 23, 2024

Greenview Inn Riverhead
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
The price is $351 per night from Sep 30 to Oct 1
$351
includes taxes & fees
$308 per night
Sep 30 - Oct 1
8.8/10 Excellent! (171 reviews)
"Great Property"

Reviewed on Sep 12, 2024

Baron's Cove
See all 4,289 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.

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 $897 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?
Use Expedia’s filter tool to help you find some of the best Cutchogue package deals. When you start your search, simply set your maximum budget and then sort the results by “Price: low to high.” If you want to save, plan your break for midweek, or search for Cutchogue package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s typically best to book your vacation package well in advance.
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?
If you’ve got your Cutchogue travel dates finalized, book as soon as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Cutchogue?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Cutchogue.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and flights. Your hotel will probably be the biggest expense during your trip to Cutchogue.
  3. Organize your Cutchogue escape with Expedia’s trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Cutchogue together.
  4. Decide how long to go for: Now that you know more about Cutchogue, you can work out the right length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Cutchogue vacation package.
  6. Add on experiences and excursions: Take a look at our travel guide to find some awesome things to do in Cutchogue. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities once you arrive.

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.

Discover the most popular places to visit in Cutchogue

Image for Bedell Cellars

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
Image for Peconic Bay Winery

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
Image for Pellegrini Vineyards

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

Image for Long Island Wine and Food Day Trip with Sommelier host from NYC

Long Island Wine and Food Day Trip with Sommelier host from NYC

$149
Per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Image for Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

$1,299
Per adult
Hamptons Private Day Trip from New York City
Image for Long Island North Fork Sights, Bites & Flights: Full-Day Tour

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

$446
Per adult
Long Island North Fork Sights, Bites & Flights: Full-Day Tour
See all activities in Cutchogue

Other vacations you might like

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