Greenport West Vacations from $464

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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.

The Latest Greenport West vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $765, price is now $464 per person
$464
per person
Feb 13 - Feb 16
found 6 hours ago
Roundtrip flight included
San Juan (SJU) to New York (NYC)
9.2/10 Wonderful! (1,002 reviews)
I stay here often and the rooms are spacious clean and the hotel staff is very accommodating. I always have a wonderful experience and I highly recommend staying here. They also offer free breakfast and dinner which is a nice perk.

Reviewed on Nov 25, 2025

Pendry Natirar

Pendry Natirar

5 out of 5
Price was $2,195, price is now $1,244 per person
$1,244
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (NYC)
9.8/10 Exceptional! (7 reviews)
The staff is lovely and the property gorgeous. The room could have been more complete (no slippers to be found and no in-room mini bar amenities, which was surprising). The grounds are pristine and peaceful.

Reviewed on Jun 13, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,969, price is now $1,132 per person
$1,132
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (NYC)
8.8/10 Excellent! (1,000 reviews)
The view is soooo good!

Reviewed on Dec 2, 2025

Chateau Grande Hotel

Chateau Grande Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,196, price is now $698 per person
$698
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to New York (NYC)
8.6/10 Excellent! (242 reviews)
My sister shared that her stay was not what she expected. She expressed that it was not Kid friendly. She indicated that she and her family had to request for clean towels daily. She is a disabled Veteran. She also shared the that she was confronted a couple of times about parking in the Handicapped space. The decal was displayed on her license plate. Hopefully the next visit would be better!

Reviewed on Dec 5, 2025

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,222, price is now $728 per person
$728
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (NYC)
9.2/10 Wonderful! (3,941 reviews)
Everyone on staff was helpful, accommodating and always smiling! We truly enjoyed staying here.

Reviewed on Dec 3, 2025

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Discover the most popular places to visit in Greenport West

67 Steps Beach

4.5/5(4 reviews)

Why not spend a carefree afternoon at 67 Steps Beach during your travels in Greenport? Take in the festivals and sunsets in the area.

67 Steps Beach

Kontokosta Winery

4/5(9 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.

Kontokosta Winery

Railroad Museum of Long Island

You can spend time studying the exhibits at Railroad Museum of Long Island during your travels in Greenport. Stroll along this family-friendly area's waterfront, or simply enjoy its wineries.

Railroad Museum of Long Island

What to do in Greenport West

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
See all activities in Greenport West

Greenport West Hotel Deals

Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
8.8/10 Excellent! (249 reviews)
The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken.

Reviewed on Nov 12, 2025

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Cliffside Resort Condominiums
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
$194 nightly
The price is $222 total per night from Jan 4 to Jan 5
$222 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.8/10 Exceptional! (139 reviews)
Just a perfect little get away! The facility was perfectly quaint yet trendy, the staff was friendly, and it was so cozy and close to all the local wineries! 10/10 recommend and I will most definitely be back!

Reviewed on Nov 15, 2025

Silver Sands Motel & Beach Bungalows
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
$77 nightly
The price is $89 total per night from Dec 8 to Dec 9
$89 total
Dec 8 - Dec 9
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
A welcoming place with some nice touches.

Reviewed on Nov 30, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,166 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.

Find the Best Greenport West Vacation Packages

Greenport West Essential Information

Language
English
Currency
U.S dollars
Population
2,100
Top Sights
67 Steps Beach, Kontokosta Winery and Railroad Museum of Long Island

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Frequently asked questions

How much does a Greenport West vacation package cost?
Offering excellent value package deals from $464 on Expedia, you'll be pleasantly surprised at how much a vacation to Greenport West costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Greenport West?
You can typically find reduced prices and better availability in November, December and January. Check out our cheap Greenport West vacation packages and you could land some great off-season deals.
How many days is enough for Greenport West?
The ideal length for your Greenport West vacation depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to hit all the major sights and discover some hidden gems along the way.
How to find the best Greenport West package deals?
Use Expedia's filter tool to find some terrific Greenport West package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Greenport West package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Greenport West vacation as a package?
You can enjoy significant savings on your Greenport West getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Greenport West?
If you've got your Greenport West vacation dates finalized, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Greenport West?

  1. Pick your dates: The things you'd like to do in Greenport West and your favorite season can help you decide when to go.
  2. Set a budget: Factor in expenses such as food, flights and transportation when calculating how much to save for your trip to Greenport West. Then, choose a hotel that matches your budget, whether that's an economical option or a deluxe getaway.
  3. Use Expedia's trip planning tool to discover Greenport West: Research every aspect of your trip to Greenport West with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with Greenport West, you can work out the right length of your vacation. Put together a rough itinerary and give yourself enough time for all the things you want to do.
  5. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the right Greenport West vacation package for you.
  6. Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Explore some of the exciting things to do in Greenport West in Greenport West and book your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Greenport West vacation packages?
Set off on your dream getaway to Greenport West with our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.