Greenport West Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Greenport West Vacation

Book a Greenport West vacation package and get set to experience the best of this city. Consider staying in the neighborhood of Orient Point, which is good for views, fishing and nature. You'll want to take in some sights during your trip to Greenport West. Find time for leading attractions such as 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island. No matter your travel plans or the size of your budget, organizing a tailored Greenport West vacation is easy with Expedia.

Top Greenport West Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,831, price is now CA $1,119 per person
CA $1,119
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $2,681, price is now CA $1,531 per person
CA $1,531
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,566, price is now CA $1,494 per person
CA $1,494
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
Best hotel in town, I recommend it 100%

Reviewed on Nov 9, 2026

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $3,020, price is now CA $1,759 per person
CA $1,759
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (555 reviews)
Large room and very clean overall property! Staff was very friendly and was able to accommodate an early check in (without request).

Reviewed on Nov 8, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,379, price is now CA $1,402 per person
CA $1,402
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
My second time staying here and it never disappoints. Very clean, comfortable and attentive staff.

Reviewed on Nov 9, 2026

Ready to book your vacation to Greenport West?

 

Choose your dates

Greenport West Hotel Deals

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
The price is CA $274 per night from Dec 10 to Dec 11
CA $274
CA $313 total
Dec 10 - Dec 11
includes taxes & fees
Silver Sands Motel & Beach Bungalows
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
The price is CA $440 per night from Nov 10 to Nov 11
CA $440
CA $503 total
Nov 10 - Nov 11
includes taxes & fees
North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
The price is CA $271 per night from Nov 26 to Nov 27
CA $271
CA $467 total
Nov 26 - Nov 27
includes taxes & fees
Cliffside Resort Condominiums
See all 4,068 properties in Greenport West
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

Stay near popular Greenport West attractions

Kontokosta Winery

9.2/10 (48 reviews)
You can enjoy a tasting or tour at Kontokosta Winery during your travels to Greenport West. Wander the beautiful beaches in this family-friendly area.
See properties

Frequently asked questions

How much does a Greenport West vacation package cost?
Offering great value package deals from CA $1,119 on Expedia, you'll be thrilled with how little a vacation to Greenport West costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Greenport West?
January, February and November are the best times to search for cheap Greenport West vacation packages. Opting to travel in quieter months means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Greenport West?
You can visit all the leading sights in Greenport West in a few days, including the must-see East End Seaport Maritime Museum. If you're looking for a longer Greenport West vacation, check out what sort of activities and day tours are available close by.
How to find the best Greenport West package deals?
Start your search for a Greenport West package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Greenport West package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Greenport West getaway off to a flying start.
Is it cheaper to book a Greenport West vacation as a package?
You can enjoy significant savings on your Greenport West escape by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Greenport West?
If you're planning a spontaneous Greenport West vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Greenport West?

  1. Choose your travel dates: What you want to do in Greenport West and your favourite season can help you decide when to travel.
  2. Budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may crop up during your trip to Greenport West.
  3. Decide how long to go for: Now that you're more familiar with Greenport West, you can figure out the perfect length of your vacation. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Greenport West vacation package for you.

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