Cutchogue Vacation Packages

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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.

Top Cutchogue Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Aug. 8 - Aug. 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (2,453 reviews)
Really enjoyed our stay

Reviewed on Jun. 5, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 6 - Aug. 11
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
9.2/10 Wonderful! (547 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on May 28, 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Aug. 30 - Sep. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,005 reviews)
Staff amazing! Concierge amazing Daniella is always fantastic with customer service!

Reviewed on Jun. 4, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 8 - Aug. 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
The location was perfect. Nearby sights, restaurants, and easy access to transportation. The Hotel was beautiful and service was great!

Reviewed on Jun. 4, 2024

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 12 - Jul. 15
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
Great location! Great service!

Reviewed on May 20, 2024

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 CA $104 per night from Jun. 9 to Jun. 10
CA $104
CA $120 total
includes taxes & fees
Jun 9 - Jun 10
7.6/10 Good! (787 reviews)
"Very clean room, nice view of the costal area from balcony. They are under remodling so some areas were umderstamdaly rough. Bit the awesome staff find us the perfect room was appreciated. We will stay there again soon."

Reviewed on May 31, 2024

Pier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton
The Bentley Hotel Southampton
2 out of 5
161 Hills Station Rd, Southampton, NY
The price is CA $259 per night from Jun. 9 to Jun. 10
CA $259
CA $356 total
includes taxes & fees
Jun 9 - Jun 10
9.2/10 Wonderful! (76 reviews)
"Large room recently updated, didn’t hear other guests"

Reviewed on May 29, 2024

The Bentley Hotel Southampton
Hilton Garden Inn Riverhead
Hilton Garden Inn Riverhead
3 out of 5
2038 Old Country Rd, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jun. 16 to Jun. 17
CA $196
CA $223 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (1,004 reviews)
"Nice property and service in a great location."

Reviewed on May 30, 2024

Hilton Garden Inn Riverhead
See all 4,355 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cutchogue vacation package cost?
Live it up in Cutchogue from as little as CA $835. We offer a wonderful selection of hotels, flights and rental cars to suit your budget. Land even more discounts when you add some experiences or tours to your vacation package.
How do I get a cheap travel package to Cutchogue?
Booking a Cutchogue vacation package with Expedia is an easy way to save. We offer access to over 550 partner airlines and 1,000,000 properties spread across the globe. With such a fabulous range to select from, you’ll have no worries putting together your perfect adventure.
How far in advance should I book my Cutchogue vacation?
While not all airlines advertise tickets early, customers are usually able to compare international fares on Expedia up to 12 months in advance. This is the time when you’ll nab some incredible deals. If you’re booking at the last minute, you might get lucky. Low prices sometimes appear a few weeks prior to departure.
What does an Expedia Cutchogue travel package include?
Expedia has everything you need to plan your Cutchogue getaway, but how your package is structured is your call. Select from any combination of rental cars, hotels and flights. In search of a few activities to fill in your time? Once you’ve made your booking, you can add them on too. No matter your budget, there’s a package deal to meet your needs.
What should I know before booking a Cutchogue travel package?
Whether it’s adventure or relaxation you’re chasing, a Cutchogue vacation package lets you plan your escape your way. Plus, you’ll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Cutchogue Expedia vacation package?
Yes, and with over 550 airlines to choose from across the globe, you’re not short on choice. Browse the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Cutchogue vacation package?
Yes you can, and we’re here to help. You may be able to change or cancel your Cutchogue vacation package at no cost within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If life throws you a curveball, visit our Customer Service Portal for further information.

Discover the most popular places to visit in Cutchogue

Image for Bedell Cellars

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
Image for Peconic Bay Winery

Peconic Bay Winery

Enjoy an outing to Peconic Bay Winery during your stay in Cutchogue. While you're in the area, stroll along the beautiful beaches.

Peconic Bay Winery
Image for Pugliese 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

What to do in Cutchogue

Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

CA $1,623
Per adult
Private Hamptons Tour with Outlet Center Shopping
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.